Molbank doi: 10.3390/M1798
Authors: Bakr F. Abdel-Wahab Hanan A. Mohamed Benson M. Kariuki Gamal A. El-Hiti
The reaction of equimolar quantities of 3-(1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde and (2,4,6-trichlorophenyl)hydrazine in ethanol containing concentrated hydrochloric acid (0.2 mL; 37%) as a catalyst under reflux for 2 h yielded 1-(1-(benzofuran-2-yl)ethylidene)-2-(2,4,6-trichlorophenyl)hydrazine. The crude produced was purified by crystallization using dimethylformamide to provide the title heterocycle in a 95% yield. The structure of the newly synthesized heterocycle was confirmed through X-ray diffraction and spectral analyses.
]]>Molbank doi: 10.3390/M1797
Authors: Pankaj Das Catherine Elleouet François Y. Pétillon Philippe Schollhammer
The reaction of the dianionic species [Fe2(CO)6(μ-PPh)2]2− with tBuN(CH2Cl)2 gives the di-iron carbonyl aza-diphosphido-bridged complex [Fe2(CO)6(µ-{P(Ph)CH2}2NtBu)] (1). Attempts to prepare 1 by click-chemistry by reacting [Fe2(CO)6(μ-PHPh)2] with CH2O and tBuNH2 afforded a bis-phosphido compound [Fe2(CO)6(µ-P(Ph)CH2NHtBu)2] (2) which exists as two, syn and anti, isolable isomers depending on the relative orientation of the groups carried by the phosphorus atoms. In the presence of HBF4.Et2O, in dichloromethane, 1 leads to the stabilized ammonium species [Fe2(CO)6(µ-{P(Ph)CH2}2NHtBu)](BF4) (3). The derivatives 1–3 were characterized by IR and 1H, 31P-{1H} NMR spectroscopies. Their structures in a solid state were determined by X-ray diffraction analyses, which accord with their spectroscopic characteristics.
]]>Molbank doi: 10.3390/M1796
Authors: Deiby F. Aparicio Acevedo Marlyn C. Ortiz Villamizar Vladimir V. Kouznetsov
The quinoline derivative, N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide, was synthesized in a conventional three-step procedure from 4,7-dichloroquinoline using a N-oxidation reaction/C2-amide formation reaction/C4 SNAr reaction sequence. The structure of the compound was fully characterized by FT-IR, 1H-, 13C-NMR, DEPT-135°, and ESI-MS techniques. Its physicochemical parameters (Lipinski’s descriptors) were also calculated using the online SwissADME database. Such derivatives are relevant therapeutic agents exhibiting potent anticancer, antibacterial, antifungal, and antiparasitic properties.
]]>Molbank doi: 10.3390/M1795
Authors: Paul R. Palme Richard Goddard Peter Imming Rüdiger W. Seidel
4-(4-nitrophenyl)thiomorpholine, the title compound, has been used as a precursor for the corresponding 4-thiomorpholinoaniline, which is a useful building block in medicinal chemistry. The crystal and molecular structures of the title compound, however, have not been described thus far. We synthesized the title compound by means of a nucleophilic aromatic substitution reaction of 4-fluoronitrobenzene and thiomorpholine and structurally characterized it by X-ray crystallography, DFT calculations, and Hirshfeld surface analysis. In the crystal, the molecule exhibits an approximately CS-symmetric structure, with the nitrogen-bound 4-nitrophenyl group in a quasi axial position on the six-membered thiomorpholine ring in a low-energy chair conformation. The solid-state structure of the title compound is markedly different from that of its morpholine analogue. This can be ascribed to the formation of centrosymmetric dimers through intermolecular C–H···O weak hydrogen bonds involving the methylene groups adjacent to the sulfur atom and face-to-face aromatic stacking.
]]>Molbank doi: 10.3390/M1794
Authors: Diego Quiroga Ericsson Coy-Barrera
The multicomponent reaction between ʟ-tryptophan 1, 2-oxobutanoic acid 2, and 1-butanol in the presence of SiMe3Cl was studied using microwave irradiation conditions. The main product was identified as an unreported acetal-containing compound, namely, butyl (2,2-dibutoxybutanoyl)-ʟ-tryptophanate (3), yielding 89%. NMR experiments demonstrated that the adjacent methylene protons of the acetal group appeared as two signals exhibiting their behavior as diastereotopic protons. DFT/B3LYP calculations revealed an asymmetric molecular structure with specific angles, leading to an explanation of the NMR results. The calculated chemical shifts showed slight differences with the experimental values and suggested magnetic anisotropy and inductive deprotection around the methylene hydrogen atoms in the acetal location. The reaction mechanism was proposed in which SiMe3Cl plays a crucial role by promoting water removal through key steps.
]]>Molbank doi: 10.3390/M1793
Authors: Phelelisiwe S. Dube Dylan Hart Lesetja J. Legoabe Audrey Jordaan Digby F. Warner Richard M. Beteck
Nitrothiazole derivatives have been reported to exhibit activity against aerobic, anaerobic, and microaerophilic bacteria. This activity profile makes the nitrothiazole compound class an ideal lead source against Mycobacterium tuberculosis, which flourishes in varied environments with different oxygen concentrations. In this work, we investigated six nitrothiazole derivatives for antitubercular activity. The compounds exhibited potent activity, with compounds 9 and 10 possessing an equipotent MIC90 value of 0.24 µM. The compounds were investigated for cytotoxicity against HEK293 cells and hemolysis against red blood cells, and they demonstrated no cytotoxicity nor hemolytic effects, suggesting they possess inherent antitubercular activity.
]]>Molbank doi: 10.3390/M1792
Authors: Nikita S. Gudim Ekaterina A. Knyazeva Oleg A. Rakitin
Donor–π spacer–acceptor (D–π–A) dyes are among the most attractive structures for the design of organic dye-sensitized solar cells (DSSCs). Typically, the key intermediates for these sensitizers are D–π compounds containing an aldehyde group to which an anchor acceptor group is attached via the Knoevenagel reaction. In this communication, 5-(9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazol-6-yl)thiophene-2-carbaldehyde was prepared via the Suzuki cross-coupling reaction. The structure of the newly synthesized compound was established by means of high-resolution mass spectrometry, 1H NMR, 13C NMR, IR, and UV–Vis spectroscopy. The title compound would be used in the synthesis of sensitizers for DSSCs.
]]>Molbank doi: 10.3390/M1791
Authors: Anna Nacher-Luis Isidro M. Pastor
The study of new catalytic protocols for the synthesis of organic compounds with a more sustainable perspective is of interest. The use of ionic organic solids, such as 1,3-bis(carboxymethyl)imidazolium chloride as a catalyst has allowed the Michael addition of N-heterocycles to chalcones. This methodology has been applied to the unique preparation of the potential bioactive compound 1-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one with moderate yield, due to the retro-Michael reaction. Both synthetic reactions (i.e., preparation of chalcone and triazole Michael-addition to chalcone) have good green metrics.
]]>Molbank doi: 10.3390/M1790
Authors: Bakr F. Abdel-Wahab Hanan A. Mohamed Benson M. Kariuki Gamal A. El-Hiti
The reaction of a mixture of equimolar quantities of 2-acetylbenzofuran and (2,4,6-trichlorophenyl)hydrazine in ethanol containing concentrated hydrochloric acid (0.2 mL; 37%) as a catalyst under reflux for two hours yielded 1-(1-(benzofuran-2-yl)ethylidene)-2-(2,4,6-trichlorophenyl)hydrazine. The crude product was purified by crystallization using dimethylformamide to provide the title heterocycle in a 90% yield. The structure of the new heterocycle was confirmed through X-ray diffraction and spectral analyses.
]]>Molbank doi: 10.3390/M1789
Authors: Bakr F. Abdel-Wahab Hanan A. Mohamed Benson M. Kariuki Gamal A. El-Hiti
The reaction of (E)-2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one and (2,4-dinitrophenyl)hydrazine in boiling ethanol containing hydrochloric acid (0.2 mL; 37%) for 1.5 h gave 1-(2,4-dinitrophenyl)-2-(2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine in a 90% yield. Various spectral analyses, including NMR, and X-ray crystallography established the structure of the newly synthesized hydrazone.
]]>Molbank doi: 10.3390/M1788
Authors: Roman P. Kustin Oleg V. Levin Sofia S. Filippova Elena V. Alekseeva
TEMPO-containing conductive polymers are used in organic electronics due to their electrochemical properties. One of significant limitations in developing such materials is the structural modification by several TEMPO moieties. Here, we report a synthesis of the first-generation dendrimer containing two TEMPO fragments, bis(2,2,6,6-tetramethyl-1-(λ1-oxidaneyl)piperidin-4-yl) 3,3′-((2-hydroxyethyl)azanediyl)dipropionate, that can be implemented into a conductive polymer structure. The resulting product was characterized using 1H and 13C nuclear magnetic resonance spectroscopy (NMR) and high-resolution mass spectroscopy (HRMS).
]]>Molbank doi: 10.3390/M1787
Authors: Anton A. Shetnev Julia A. Efimova Mikhail K. Korsakov Anél Petzer Jacobus P. Petzer
4-(2-Methyloxazol-4-yl)benzenesulfonamide was synthesized by the reaction of 4-(2-bromoacetyl)benzenesulfonamide with an excess of acetamide. The compound was evaluated as a potential inhibitor of human monoamine oxidase (MAO) A and B and was found to inhibit these enzymes with IC50 values of 43.3 and 3.47 μM, respectively. The potential binding orientation and interactions of the inhibitor with MAO-B were examined by molecular docking, and it was found that the sulfonamide group binds and interacts with residues of the substrate cavity. 4-(2-Methyloxazol-4-yl)benzenesulfonamide showed no cytotoxic effect against human stromal bone cell line (HS-5) in the concentration range of 1–100 µmol. Thus, the new selective MAO-B inhibitor was identified, which may be used as the lead compound for the development of antiparkinsonian agents.
]]>Molbank doi: 10.3390/M1786
Authors: Dennis M. Seth Rory Waterman
The titanium amidate compound bis(N-tert-butylacetamido)(dimethylamido)(chloro)titanium was synthesized by the protonolysis of tris(dimethylamido)(chloro)titanium and structurally characterized by 1H and 13C NMR spectroscopy as well as X-ray diffraction. The compound does not appear to react cleanly nor readily with routine alkylating agents such as sec-butyllithium, benzyl potassium, or trimethylsilyl methyllithium.
]]>Molbank doi: 10.3390/M1785
Authors: Olha-Maria Fedusevych Andrii Lozynskyi Marta Sulyma Roman Lesyk
In this work, the title compound was synthesized via the Claisen–Schmidt condensation of a 2-((5-acetyl-4-methylthiazol-2-yl)amino)isoindoline-1,3-dione with 2-fluorobenzaldehyde. The structure of the synthesized compound (yield 62%) was confirmed by 1H, 13C NMR, and LC–MS spectra. According to US NCI protocols, the compound displayed a high level of antimitotic activity against tested human tumor cells, with mean GI50/TGI values of 15.72/50.68 μM. The drug-like properties of the synthesized compound were evaluated using SwissAdme, revealing satisfactory drug-like parameters, and it presents interest for the design of new synthetic agents with biological activity.
]]>Molbank doi: 10.3390/M1784
Authors: Haruka Nishino Bo-Tao Zhang Hajime Uchida Michiya Kamio Hiroshi Nagai Masayuki Satake
A novel oxylipin, okeanoate (1), was isolated from the Okinawan cyanobacterium Okeania hirsuta. The structure of 1 was elucidated based on spectroscopic data including 1D and 2D NMR, as well as high-resolution mass spectrometry. This is the first oxylipin with a dimethylsulfonium moiety in the middle of the hydrocarbon chain.
]]>Molbank doi: 10.3390/M1783
Authors: Bastien Moreno Isabelle Jourdain Michael Knorr Sarra Boudriga Carsten Strohmann Tobias Schrimpf
To extend the existing library of arylidenerhodanines which display a potential biological activity, 3-N-allylrhodanine 1 was condensed under Knoevenagel conditions with p-nitrobenzaldehyde in acetic acid to afford the π-conjugated heterocyclic compound 3-allyl-5-(4-nitrobenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one 2. Compound 2 was characterized by IR and NMR spectroscopy, and its UV-vis spectrum was compared with that of compound 3-allyl-5-(4-methoxybenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one 3. The molecular structure is ascertained by a single-crystal X-ray diffraction study performed at 100 K.
]]>Molbank doi: 10.3390/M1782
Authors: Gabrielė Varvuolytė Aurimas Bieliauskas Neringa Kleizienė Asta Žukauskaitė Algirdas Šačkus
Herein, we describe the synthesis of 3-(2-chloroethoxy)-1-(4-methoxyphenyl)-1H-pyrazole-4-carbaldehyde via the Vilsmeier-Haack reaction. The structure of this previously unreported compound is thoroughly elucidated through NMR, FT-IR spectroscopy and HRMS spectrometry.
]]>Molbank doi: 10.3390/M1781
Authors: Narimi Hosoda Akihiko Ishii Norio Nakata
The title complex [{PhS(tBuN)2}(Cl)Ge:→RhCl(cod)] (2) was synthesized by the reaction of three-coordinated chlorogermylene, [PhS(tBuN)2]GeCl (1), supported by a diimidosulfinate ligand with a half equivalent of [RhCl(cod)]2 in benzene. The molecular structure of 2 was determined by 1H and 13C NMR spectroscopies and single-crystal X-ray diffraction (SCXRD) analysis. The electronic property of germylene 1 was assessed by determining the Tolman electronic parameter of the corresponding cis-dicarbonyl Rh(I) complex, [{PhS(tBuN)2}(Cl)Ge:→RhCl(CO)2] (3), that was prepared by the treatment of 2 with carbon monoxide.
]]>Molbank doi: 10.3390/M1780
Authors: Nikolai S. Li-Zhulanov Artem D. Rogachev Yuri V. Gatilov Konstantin P. Volcho Nariman F. Salakhutdinov
The reaction of (−)-nopol mesylate with piperazine in acetonitrile under reflux, afforded symmetric 1,4-bis(2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl)piperazine in a good yield. The compound was fully characterized and its structure was confirmed using X-ray diffraction analysis.
]]>Molbank doi: 10.3390/M1779
Authors: Laura Giraldo-Arroyave Andrés F. Yepes Wilson Cardona-Galeano
A series of 5-fluorouracil/coumarin and 5-fluorouracil/chromone hybrids were synthesized with good yields using click chemistry as the key step. The structures of these compounds and all intermediates were elucidated by spectroscopic analysis. Furthermore, pharmacokinetic and drug-like computations taken together indicated that the novel hybrids have a strong possibility to advance to further biological studies.
]]>Molbank doi: 10.3390/M1778
Authors: Plamen Angelov Pavel Yanev
2-Methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylic acid phenylamide was obtained as a single product in an experiment on the cyclization modes of a glycine-derived enamino amide. High yield and operational simplicity are the main features of the presented synthetic procedure. Additionally, this result extends our previous observations on the cyclization reactions of similarly functionalized enamines, by revealing the preferred cyclization pathway under Boc-deprotection conditions.
]]>Molbank doi: 10.3390/M1777
Authors: Chadron M. Friesen Nathan J. Weeks Scott T. Iacono
The title compound was synthesized at a near-quantitative yield using the nucleophilic aromatic substitution of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with perfluoropyridine (PFP). The purity and structure were determined by NMR (1H, 13C, 19F), GC-EIMS, and single-crystal X-ray crystallography.
]]>Molbank doi: 10.3390/M1776
Authors: Kirill A. Gomonov Vasilii V. Pelipko Igor A. Litvinov Ruslan I. Baichurin Sergey V. Makarenko
The synthesis of previously unknown 4,5-dimethylfuro[3,4-d]pyridazin-1(2H)-one has been proposed and structurally characterized via a single-crystal X-ray diffraction analysis, 1H, 13C–{1H}, 1H–13C HMQC, and 1H–13C HMBC NMR spectroscopy, and IR spectroscopy.
]]>Molbank doi: 10.3390/M1775
Authors: Diyana Dimitrova Stanimir Manolov Iliyan Ivanov Dimitar Bojilov Lyusi Kasamova Paraskev Nedialkov
In this study, we outline the eco-friendly mechanosynthesis of N-(2,2-diphenylethyl)-4-nitrobenzamide by reacting 2,2-diphenylethan-1-amine with 4-nitrobenzoyl chloride. The resulting bio-functional hybrid compound was meticulously characterized through the analysis of 1H-, 13C-NMR, UV, and detailed mass spectral analysis.
]]>Molbank doi: 10.3390/M1774
Authors: Emmanouil Broumidis Samuel B. H. Patterson Georgina M. Rosair Panayiotis A. Koutentis Andreas S. Kalogirou
3,5-Diphenyl-4H-1,2,6-thiadiazin-4-one treated with meta-chloroperoxybenzoic acid undergoes an oxidative ring contraction to give 2-benzoyl-4-phenyl-1,2,5-thiadiazol-3(2H)-one 1,1-dioxide in a 29% yield, the structure of which is supported by single-crystal X-ray diffraction analysis and the available spectroscopic data.
]]>Molbank doi: 10.3390/M1773
Authors: Enrique B. Aparicio Stephen R. Isbel Alejandro Bugarin
This communication reports a four-step protocol to produce 3-allyl-2-(allyloxy)-5-bromoaniline 5 from commercially available 2-allylphenol. The synthetic steps used were nitration, selective bromination, allylation, and reduction of the nitro group.
]]>Molbank doi: 10.3390/M1772
Authors: Maksim V. Dmitriev Ekaterina E. Khramtsova Danila Y. Apuskin Alexander I. Andreev Ilya I. Kovalenko Irina V. Mashevskaya Andrey N. Maslivets
Non-steroidal anti-inflammatory drugs (NSAIDs) are an important class of medications; however, they have some drawbacks. We are developing a new NSAID with pronounced anti-inflammatory and analgesic activities and a very low toxicity—(Z)-3-(2-oxo-2-(p-tolyl)ethylidene)piperazin-2-one (piron). In this work, we describe the synthesis of the main metabolite of piron—(Z)-4-(2-(3-oxopiperazin-2-ylidene)acetyl)benzoic acid. The anti-inflammatory activity of the synthesized metabolite was determined in vivo.
]]>Molbank doi: 10.3390/M1771
Authors: Niall Hehir John F. Gallagher
The title compound N-(2,4-difluorophenyl)-2-fluorobenzamide (Fo24) was synthesized in high yield (1.09 g; 87%) using standard synthetic procedures from the condensation reaction of 2-fluorobenzoyl chloride with 2,4-difluoroaniline. Crystals of Fo24 were grown from CH2Cl2 at room temperature. The Fo24 crystal structure was determined using single-crystal X-ray diffraction methods at 294 (1) K in space group Pn (No. 7). Fo24 is the second regular tri-fluorinated benzamide with the formula C13H8F3N1O1 to be reported and contrasts with the more common difluorinated and tetra-fluorinated analogues. In Fo24, both aromatic rings are effectively coplanar with an interplanar angle of 0.7(2)°. The central amide group plane is oriented by 23.04(18)° and 23.69(17)° from both aromatic rings, forming an intramolecular contact with an ortho-F12 atom with H1⋯F12 = 2.12(4) Å. The primary hydrogen bonds are 1D amide–amide interactions that form along the b-axis direction. In addition, weaker C-H⋯F/O interactions are noted: a R22(12) synthon involving two C-H, a N-H and two C-F groups, with C-F⋯C ring–ring stacking contacts completing the interactions.
]]>Molbank doi: 10.3390/M1770
Authors: Stefan Weigand Karlheinz Sünkel
Treatment of 2-pyridyl-ferrocene wit [Cp*IrCl2]2 in the presence of NaOAc produces the title compound Cp*ClIr[(C5H3C5H4N-кN,кC)Fe(C5H5)] (2) in low yield. A crystal structure determination shows the (SpSIr/RpRIr)-2 enantiomeric pair of diastereomers.
]]>Molbank doi: 10.3390/M1769
Authors: Nobuyoshi Morita Saki Kurami Naho Ishii Kosaku Tanaka Yoshimitsu Hashimoto Osamu Tamura
One-pot synthesis of (E)-5-[bromo(phenyl)methylene]-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole (9) from propargylic alcohol 5 and p-toluamide (6) was achieved via gold(III)-catalyzed propargylic substitution, followed by gold(III)-catalyzed bromocyclization. The structure of 9 was confirmed by an X-ray crystallographic analysis.
]]>Molbank doi: 10.3390/M1768
Authors: Kristina Svetlova Alexander Kazantsev Oleg Levin Sofia Filippova Elena Alekseeva
Carbazole polymers attract significant attention as promising luminophores, organic electronic and photovoltaic materials, photo/electrocatalysts, energy storage materials, redox mediators and catalysts. However, the oxidation potential of the commercially available poly(vinylcarbazole) is insufficient for some applications such as high-voltage Li-Ion batteries. We have proposed a monomer for the novel polycarbazole with an increased oxidation potential, which will be compatible with high-voltage cathode materials for Li-Ion. In addition, the proposed polymer is an interesting substrate for the further carbonization to obtain N-doped carbons with a high electrocatalytic activity level.
]]>Molbank doi: 10.3390/M1767
Authors: Gavin R. Hoffman Allen M. Schoffstall
Intramolecular cycloadditions have the great advantage of forming two rings simultaneously. We report the use of intramolecular [3 + 2] cycloaddition of the nitrile oxide derived from an N-propargylbenzimidazole oxime in the synthesis of a hitherto unreported tetracyclic isoxazole-containing ring system bearing “6-5-5-5”-membered ring fusions. The initial condensation was achieved through reaction of o-phenylenediamine with ethyl diethoxyacetate, followed by alkylation with propargyl bromide, deprotection of the acetal to the aldehyde, formation of an aldoxime, and intramolecular nitrile oxide cycloaddition (INOC). Characterization of the aldoxime and tetracyclic isoxazole is included herein.
]]>Molbank doi: 10.3390/M1766
Authors: Petr A. Buikin Anna V. Vologzhanina Alexander A. Korlyukov
1-(3-(2-(Dimethylammonio)ethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide succinate (sumatriptan succinate, HSum+·HSucc−) is a serotonin receptor agonist used to treat migraines. By the recrystallization of this substance from ethanol, its hemi(ethanol solvate), HSum+·HSucc−·0.5EtOH, was obtained. The solid was characterized by X-ray diffraction and FT-IR spectroscopy. In HSum+·HSucc−·0.5EtOH, solvent molecules link succinate anions into infinite O–H…O bonded chains, which are further connected by N–H…O interactions with cations into H-bonded layers.
]]>Molbank doi: 10.3390/M1765
Authors: Ildar R. Iusupov Victor A. Tafeenko Andrea Altieri Alexander V. Kurkin
This work describes the synthesis of spirocyclic compounds based on 8-azaspiro[5.6]dodec-10-ene. Diastereomerically pure pyrrole derivatives were prepared from the spirocyclic 1,2,3-triazole using a coupling reaction. The resulting compounds were characterized via 1H and 13C NMR spectroscopy and HRMS, and the crystallographic characteristics of one of them were studied via X-ray diffraction.
]]>Molbank doi: 10.3390/M1764
Authors: Tatiana S. Vlasova Yulia E. Romanova Ilya V. Taidakov Stanislav A. Paveliev
In this work, the title compound was synthesized via the reaction of an aryl-substituted pyrazole with potassium tetrachloroplatinate, followed by the reaction of the postulated intermediate chloro-bridged dimer with a pyrazole-containing 1,3-diketonate ligand. The structure of the synthesized complex was established by 1H, 13C NMR spectroscopy and mass spectrometry. According to UV-Vis spectrometry studies, the obtained complex exhibits green fluorescence with a maximum at 514 nm. Based on cyclic voltammetry studies, the HOMO, LUMO and band gap values were calculated.
]]>Molbank doi: 10.3390/M1763
Authors: Rusi Rusew Kostadin Iliev Vanya Kurteva Boris Shivachev
The title compound 1-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl) quinolin-1-ium bromide was obtained in good yield by a facile one-pot, one-step synthetic procedure involving quinoline and an aromatic α-bromo ketone. The product was isolated using hot recrystallization from acetone/acetonitrile solution and characterized using powder and single-crystal XRD, 1D and 2D NMR, DSC, FT-IR, and HRMS analyses.
]]>Molbank doi: 10.3390/M1762
Authors: Cosimo Antonini Franca M. Cordero Fabrizio Machetti
We describe here the palladium hydrogenation of ethyl 5-(benzoyloxymethyl)isoxazole-3-carboxylate. The presence of two reducible sites in the molecule, namely the benzylic-like position and the isoxazole N–O bond, creates a possible competition. The results show that under the applied conditions, ethyl (Z)-2-amino-4-oxo-2-pentanoate is obtained as the only product. Accordingly, a domino process occurs, consisting of deoxygenation to the 5-methylisoxazole derivative followed by reductive opening of the isoxazole ring. The isoxazole substrate was prepared by NaOH-catalyzed cycloaddition-condensation of ethyl nitroacetate and propargyl benzoate in water. Complete characterizations of the isoxazole and Z-enaminone derivatives are reported.
]]>Molbank doi: 10.3390/M1761
Authors: Andreas S. Kalogirou Panayiotis A. Koutentis
Stille coupling between 5,5′-dibromo-4,4′-diphenyl-2,2′-bithiazole and 9-(2-ethylhexyl)-3-(tributylstannyl)-9H-carbazole in the presence of Pd(Ph3P)2Cl2 in toluene, heated at reflux for 2 h, gave 5,5′-bis[9-(2-ethylhexyl)-9H-carbazol-3-yl]-4,4′-diphenyl-2,2′-bithiazole in 85% yield.
]]>Molbank doi: 10.3390/M1760
Authors: Marija Matković
Diarylethene (DAE) molecular photoswitches draw attention as building units in the preparation of diverse photoactive molecules. An interesting class of these molecules are photoactive peptides. A way to build DAE moiety into peptides/peptidomimetics is via DAE amino acids, an example of which has been demonstrated in bioactive cyclic peptides, wherein the DAE Fmoc-amino acid was prepared and used. Herein, the preparation of DAE Boc-amino acid is presented using a modified method of synthesis. This contribution to the DAE amino acid collection could be useful in the further enhancement of diversity in designing different routes to photoactive peptides.
]]>Molbank doi: 10.3390/M1759
Authors: Petr A. Buikin Anna V. Vologzhanina Roman A. Novikov Alexander A. Korlyukov
Alectinib hydrochloride is an anticancer medication used for the first-line treatment of non-small cell lung cancer. Although it was approved for medical use ten years ago, and three polymorphs of this substance were proposed based on X-ray diffraction patterns, their crystal structures remained unknown to date. The main problem was the preparation of high quality single crystals due to the very low solubility of the salt. Herein, we report on the molecular and crystal structure of form I of alectinib hydrochloride as obtained using powder X-ray diffraction data from a laboratory source. Short Cl…N distances between the anion and the nitrogen atoms of the morpholine and benzo[b]carbazole rings indicate the positions of the H(N) atoms. As a result, the cation and anion form infinite Cl…H(N)-bonded chains.
]]>Molbank doi: 10.3390/M1758
Authors: Regina A. Tuktarova Lilya U. Dzhemileva Usein M. Dzhemilev
For the first time, a synthetic analogue of natural (5Z,9Z)-dienoic acid has been synthesized in the form of a hybrid molecule containing a fragment of oleanolic acid and (5Z,9Z)-tetradeca-5.9-dienedicarboxylic acid, synthesized using a new reaction of Ti-catalyzed homo-cyclomagnesiation 1,2-dienes. The high cytotoxic activity of (5Z,9Z)-14-[(3,28-dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic acid against tumor cells Jurkat, K562, U937 and HL60 was established. This compound is also an inducer of apoptosis, affects the cell cycle and inhibits human topoisomerase I.
]]>Molbank doi: 10.3390/M1757
Authors: Anastasia A. Andreeva Maksim V. Dmitriev Andrey N. Maslivets
The reaction of 4-(4-bromophenyl)-2,4-dioxobutanoic acid with thiosemicarbazide, in a ratio of 1:2, when boiled in ethanol gives 3-(4-bromophenyl)-1-carbamothioyl-5-(2-carbamothioylhydrazinyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid with a good yield. This compound was fully characterized.
]]>Molbank doi: 10.3390/M1756
Authors: Dawid J. Kucharski Przemysław J. Boratyński
An unexpected diastereoselective C-alkylation of a mefloquine derivative in up to 57% yield was the result of an attempted Williamson etherification of Boc-mefloquine. The domino reaction involved oxazolidinone ring closure, deprotonation, and stereoselective carbon–carbon bond formation. The structure was confirmed with 2D NMR experiments.
]]>Molbank doi: 10.3390/M1755
Authors: Marwa Essid Chakib Hrizi Salah Ammar Abderrahim Khatyr Michael Knorr Annika Schmidt Carsten Strohmann
The olefinic dithioether (Z)-1,4-bis(pyridin-2-ylthio)but-2-ene Z-PyS(CH2CH=CHCH2)SPy (L) was prepared by the treatment of cis-ClCH2CH=CHCH2Cl with in situ generated potassium pyridine-2-thiolate Py-SK and analyzed by IR and NMR spectroscopy. To investigate the chemistry of polynuclear iodobismuthate complexes, two equivalents of BiI3 were reacted with L in the MeOH solution to afford the anionic tetranuclear title compound (C14H15S2N2)2(C9H10SN)2[Bi4I116] with a N-protonated (Z)-1,4-bis(pyridin-2-ylthio)but-2-ene as a counterion. Compound 1 was characterized by IR and UV spectroscopy; the formation of a tetranuclear framework was ascertained by a single-crystal X-ray diffraction study performed at 100 K. Furthermore, an unusual Bi(III)-meditated cyclization of one Z-PyS(CH2CH=CHCH2)SPy ligand occurred, affording the bicyclic pyridinium salt 3-vinyl-2,3-dihydrothiazolo[3,2-a]pyridinium bearing a terminal vinyl group, compensating the second negative charge of the Bi4I164− cluster anion. The SCXRD characterization was completed by a Hirshfeld surface analysis, revealing some secondary interactions occurring in the crystal.
]]>Molbank doi: 10.3390/M1754
Authors: Aziz Alabed Kwaku Kyeremeh Hai Deng
In our continued desire to isolate more bioactive compounds from the Streptomyces sp. MA37 variant, ΔaccJ, three new accramycin derivatives have been successfully characterised. The structures of accramycin L-N (1–3) were established by high-resolution mass spectrometry and 1D and 2D nuclear magnetic resonance. The antimicrobial evaluation of accramycin L-N against Staphylococcus aureus, Klebsiella pneumoniae, and Enterobacter cloacae showed minimum inhibitory concentration (MIC) values ranging from 0.77 to 13.02 µg/mL. Accramycin L exhibited the most significant activity against S. aureus. In addition, accramycin L-N (1–3) displayed significant activity against K. pneumoniae at the MIC values of 0.81, 0.77, and 0.79 µg/mL, respectively.
]]>Molbank doi: 10.3390/M1753
Authors: Enrico Podda Eleanor Dodd Massimiliano Arca M. Carla Aragoni Vito Lippolis Simon J. Coles Anna Pintus
N,N′-Dipropyloxamide (1) was synthesised by the reaction between diethyloxalate and n-propylamine in ethanol. Compound 1 was fully characterised by both microanalytical (elemental analysis, melting point determination) and spectroscopic means (FT-IR and NMR spectroscopy). Crystals suitable for single crystal X-ray diffraction were isolated by the slow evaporation of a methyl alcohol solution of the compound. The resulting crystal structure shows the prominent role exerted by intermolecular hydrogen bonds in the crystal packing.
]]>Molbank doi: 10.3390/M1752
Authors: Evelyn Popa Adelina A. Andelescu Valentin Badea Paula Svera (m. Ianăşi) Elisabeta I. Szerb
The present paper describes the preparation and characterization of a new dinuclear ligand based on terpyridine featuring a diselenide unit. This new compound was synthesized in a two-step procedure that first involved the insertion of the diselenide moiety on a carboxylic acid and was followed by a Steglich esterification reaction between the biscarboxylic acid containing the diselenide unit and 2,6-di(pyridin-2-yl)pyridin-4-ol (tpyOH). The title compound was characterized via FT-IR, Raman, NMR (1D and 2D), and UV-Vis spectroscopies and elemental analysis. Emission properties were investigated.
]]>Molbank doi: 10.3390/M1751
Authors: Nikita A. Tretyakov Andrey N. Maslivets
The reaction of 8-(4-bromobenzoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-1,6,7-trione with benzylamine in acetonitrile at room temperature afforded a good yield of (Z)-1-benzyl-5-(4-bromophenyl)-5-hydroxy-4-(2-oxomorpholin-3-ylidene)pyrrolidine-2,3-dione. The compound was fully characterized.
]]>Molbank doi: 10.3390/M1750
Authors: Oscar Leonardo Avendaño Leon Christophe Curti Hussein El-Kashef Youssef Kabri Sébastien Redon Patrice Vanelle
As part of our ongoing attempt to broaden the applications of the amidoxime moiety as a potential source of new antileishmanial agents, this study focuses on the product 4-(5-Benzyl-3-((4-fluorophenyl)sulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-2-nitrobenzamide. This unexpected amide was obtained in an 85% yield as the major product with a conventional amidoxime synthesis protocol (Ethanol/Na2CO3) involving the reaction of hydroxylamine and a nitrile group. The formation of this amide derivative instead of the expected amidoxime can be attributed to two complementary effects: the strong electron effect of the nitro group and the influence of ethanol, a polar protic solvent. Alternatively, the desired amidoxime derivative, 4-(5-benzyl-3-((4-fluorophenyl)sulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-N′-hydroxy-2-nitrobenzimidamide, was obtained in an 80% yield by an alternative protocol (DMSO/KOtBu). This original compound, featuring a nitro group in the ortho position to the amidoxime, will be further evaluated, both in the field of medicinal chemistry and in other relevant areas, highlighting an unusual method to access amidoximes from hindered substrates.
]]>Molbank doi: 10.3390/M1749
Authors: Ekaterina A. Lystsova Ekaterina E. Khramtsova
The reaction of 3-benzoylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-trione with 2,3-dimethylquinoxaline afforded 3-benzoyl-2-hydroxy-3a-[(3-methylquinoxalin-2-yl)methyl]-1H-pyrrolo[2,1-c][1,4]benzothiazine-1,4(3aH)-dione in a moderate yield. The compound was fully characterized.
]]>Molbank doi: 10.3390/M1748
Authors: Ivan Lentin Ilia Korniltsev Alexander Gorbunov Dmitry Cheshkov Stanislav Bezzubov Vladimir Kovalev Ivan Vatsouro
Copper(I)-catalyzed azide-alkyne cycloaddition was employed to construct biscalixarene assemblies from the calix[4]arene dipropargyl ethers and 4,4′-bis-azidomethylated azobenzene or stilbene. Three bis(calixarenes) having the calix[4]arene cores linked to each other by pairs of (E)-azobenzene/stilbene units through four triazole groups were obtained as confirmed by NMR, HRMS and X-ray diffraction data. Nevertheless, the formation of larger macrocycles and polymeric/oligomeric products was found to be the major competing process that seriously limited the applicability of the one-step macrocyclization approach for the construction of photoresponsive biscalixarene assemblies linked by pairs of azobenzene/stilbene units.
]]>Molbank doi: 10.3390/M1747
Authors: Arkadiusz Sokal Roman Wrzalik Joanna Klimontko Elwira Chrobak Ewa Bębenek Monika Kadela-Tomanek
Quinoline and isoquinoline moieties occur in many natural and synthetic compounds exhibiting high biological activity. The purpose of this study was to analyze the chemical structures of 5,8-quinolinedione and 5,8-isoquinoline derivatives using FT-IR spectroscopy supplemented with theoretical DFT calculations. Spectroscopic measurements were conducted using the attenuated total reflection (ATR) mode in the frequency range of 4000–400 cm−1. An analysis of FT-IR spectra was carried out, assigning the characteristic vibration frequencies of various functional groups to individual peaks. It was found that the experimental and calculated FT-IR spectra showed a good correlation for all the compounds under study. The most significant difference in the spectra occurred in the region of carbonyl bands. For compounds with the 5,8-quinolinedione moiety, two separated C=O vibration peaks were observed, while for compounds with the 5,8-isoquinolinedione moiety, the carbonyl vibrations created only one peak. This difference makes it possible to distinguish between the 5,8-quinolinedione and 5,8-isoquinolinedione derivatives.
]]>Molbank doi: 10.3390/M1746
Authors: Nadezhda V. Danilenko Mariia O. Lutsuk Svetlana E. Patlasova Elena I. Korotkova Andrei I. Khlebnikov
New 2-(4-(fluorosulfonyloxy)phenyl)benzoxazole (2) was synthesized through the SuFEx click reaction in a two-chamber reactor. The effect of silylation on the yield of the target compound was investigated. The fluorescent properties of compound 2 were determined using experimental and computational methods.
]]>Molbank doi: 10.3390/M1744
Authors: Tanjia M. Syeda Muadh R. Al-Shaidi Ibtihal Basri Mahboub Merzouk Fawaz Aldabbagh
Treatment of the non-purified mixture of dinitro isomers obtained from the nitration of 1,4-dimethoxybenzene with piperidine led to the isolation of novel but minor adduct, 1-(2,5-dimethoxy-4-nitrophenyl)piperidine (2b) in 15% yield. Yields of nucleophilic aromatic substitution adducts are high when using purified 1,4-dimethoxy-2,5-dinitrobenzene (1b) with piperidine and pyrrolidine to give (2b) and 1-(2,5-dimethoxy-4-nitrophenyl)pyrrolidine (3b) in 76% and 82% yield, respectively.
]]>Molbank doi: 10.3390/M1745
Authors: Wilson Castrillón-López Andrés F. Yepes Wilson Cardona-Galeano
A series of 5-FU-ASA hybrids were synthesized with good yields using click chemistry as the key step. The structures of these compounds were elucidated by spectroscopic analysis. Finally, an optimal pharmacokinetic profile was also estimated for each synthetized hybrid. Taken together, hybrids 4a–h could be used as starting points for further pharmacological studies concerning therapeutic cancer intervention.
]]>Molbank doi: 10.3390/M1743
Authors: Kseniya S. Kovaleva Olga I. Yarovaya Irina A. Chernyshova Alexandra L. Zakharenko Sergey V. Cheresiz Amirhossein Azimirad Andrey G. Pokrovsky Olga I. Lavrik Nariman F. Salakhutdinov
New imidazolidine-2,4,5-triones with norabietic, nordehydroabietic, and adamantane substituents were synthesized by reacting oxalyl chloride and the corresponding ureas, providing good yields. Bioisosteric replacement of the ureide group with a parabanic acid fragment made it possible to increase the solubility of compounds and conduct biological studies. The compounds inhibit the DNA repair enzyme tyrosyl-DNA phosphodiesterase 1 in submicromolar concentrations. Cytotoxic concentrations were also studied on the glioblastoma cell line SNB19.
]]>Molbank doi: 10.3390/M1742
Authors: Lorenza Romagnoli Andrea D’Annibale Alessandro Latini
Despite having been known for a long time, quaternary 4,4′-bipyridinium salts, or viologens, are still a highly inspiring class of compounds, thanks to their peculiar redox and charge transfer properties. However, more complex structures containing multiple pyridinium rings, also interspaced by conjugated moieties, allow an even wider synthetic variability and tunability of their characteristics. The compound described herein is a star-shaped, fully conjugated molecule with three methylated pyridinium rings connected by a triple bond spacer to a central benzene core, which was synthesized from readily available building blocks, representing a quite simple model of multi-pyridyl extended viologen; its UV–visible absorption and fluorescence spectra have also been investigated.
]]>Molbank doi: 10.3390/M1741
Authors: Ewa Bębenek Monika Kadela-Tomanek Beata Filip-Psurska Elwira Chrobak
New derivative of 28-acetylbetulin containing a phenylpropynoyl moiety at the C-3 position was obtained by Steglich method. The chemical structure of this compound has been determined through 1H NMR, 13C NMR, IR, EI MS and HRMS. The antiproliferative effects of 28-O-acetyl-3-O’-(phenylpropynoyl)betulin were evaluated against three human cancer cell lines: T47D (breast cancer), CCRF/CEM (leukemia), SW707 (colorectal adenocarcinoma) and murine cell line P388 (leukemia). The synthesized compound exhibited moderate antiproliferative activity against P388 cells (IC50 = 35.51 µM). The in silico analysis showed that the title compound meets the criteria of Veber’s rule.
]]>Molbank doi: 10.3390/M1740
Authors: Stefano D’Errico Annalisa Guaragna
This Special Issue, “Molecules from Side Reactions II”, belongs to the section Organic Synthesis of the journal Molbank and was launched in 2021, after the first edition, “Molecules from Side Reactions” [...]
]]>Molbank doi: 10.3390/M1739
Authors: Anastasiya V. Petrova Irina V. Zueva Konstantin A. Petrov
In this study, the synthesis and biological activities of previously and newly synthesized oleanolic acid derivatives containing seven-membered cyclic amines at the C28 position were described. The obtained compounds were fully characterized via 1H and 13C NMR spectroscopy, and the bioactivity was evaluated by Ellman’s method. Among the tested compounds, 2,3-indolo-oleanolic acid was found to be the most active compound with an IC50 value of 0.78 µM against acetylcholinesterase. These results are significant due to the fact that research on the inhibition of acetylcholinesterase and butyrylcholinesterase enzymes by oleanolic acid, in particular indoloderivatives, is limited.
]]>Molbank doi: 10.3390/M1738
Authors: Lorenzo Suigo Valentina Straniero Ermanno Valoti
In this work, we report the unexpected conversion of a pyridine derivative into the corresponding N-benzylated pyridinium salt due to the presence of unreacted benzyl bromide in the crude product. This transformation was observed at room temperature in a solvent-free environment and without any stirring. These interesting data show how pyridinium salts can be formed in mild conditions, avoiding high temperatures that could promote the degradation of the desired product.
]]>Molbank doi: 10.3390/M1737
Authors: Paul R. Palme Richard Goddard Markus Leutzsch Adrian Richter Peter Imming Rüdiger W. Seidel
Betaines of squaric acid have gained research interest because of their structural and spectral properties. We elucidated the crystal and molecular structure of the triethylammonium betaine of squaric acid (1) by X-ray crystallography, IR, and NMR spectroscopy augmented by Hirshfeld surface analysis and DFT calculations. The crystal structure determination using Hirshfeld atom refinement reveals that the resonance hybrid structure with partial enolate character of the two lateral squaric acid C=O groups describes 1 best. The solid-state supramolecular structure features weak intermolecular C−H···O hydrogen bonds. The number of C=O bands in the IR spectrum in the solid-state is consistent with local C2v symmetry of the squaric acid residue in 1. The 13C NMR signals of this group in solution were assigned based on 2D NMR experiments and computational prediction using the Gauge-Independent Atom Orbital (GIAO) method. The present study provides the first structural characterization of a betaine of squaric acid containing a four-coordinate nitrogen atom directly attached to the four-membered ring.
]]>Molbank doi: 10.3390/M1736
Authors: Oscar Leonardo Avendaño Leon Christophe Curti Fabiana Maia Santos Urbancg Moncorvo Youssef Kabri Sébastien Redon Eduardo Caio Torres-Santos Romain Paoli-Lombardo Patrice Vanelle
As part of our ongoing research into the antileishmanial properties of amidoxime derivatives, we report a preliminary assessment of the antiparasitic properties of a novel compound, diethyl (5-benzyl-2-(4-(N′-hydroxycarbamimidoyl)phenyl)-5-methyl-4,5-dihydrofuran-3-yl)phosphonate. This compound was evaluated in vitro for the first time against the promastigote form of Leishmania amazonensis. Compounds containing both amidoxime and phosphonyl functional groups in dihydrofuran scaffolds are relatively rare, despite the extensive study of this heterocycle in various biological applications. Therefore, this work makes a valuable contribution to the fight against Leishmania spp. as a neglected disease. The cyclized 4,5-dihydrofuran intermediate scaffold was obtained via a three-step synthetic route that had previously been developed for accessing other derivatives, including the sulfone moiety. This synthesis was performed using a manganese-based free radical oxidative method under microwave irradiation. The intermediary 4,5-dihydrofuran, which included a nitrile group, tolerated the subsequent reaction with hydroxylamine hydrochloride, resulting in the formation of the target product. The target compound showed moderate activity in vitro against the promastigote form of L. amazonensis (IC50 = 91.1 µM).
]]>Molbank doi: 10.3390/M1735
Authors: Camille Blouet Stéphanie Letast Thomas Robert Stéphane Bach Noël Pinaud Nicolas Joubert Marie-Claude Viaud-Massuard Jean Guillon Cédric Logé Caroline Denevault-Sabourin
Potassium 6-oxo-7,13,16,22-tetraazatetracyclo[12.6.2.18,12.017,21]tricosa-1(20),8(23),9,11,14,16,18,21-octaen-2-yne-15-carboxylate was synthesized through a multi-step pathway, starting from commercially available 3-iodo-1,2-phenylenediamine. Structure characterization of this new substituted macrocyclic quinoxaline compound was achieved using 1H NMR, 13C NMR, and HRMS spectral analysis. This new macrocyclic derivative demonstrated submicromolar potency on both Pim-1 and Pim-2 isoforms, with an interesting selectivity profile against a selected panel of human kinases.
]]>Molbank doi: 10.3390/M1734
Authors: Irina V. Ilyina Nikolai S. Li-Zhulanov Yuri V. Gatilov Konstantin P. Volcho Alexander Yu. Sidorenko Vladimir E. Agabekov Nariman F. Salakhutdinov
The development of highly efficient methods for the synthesis of chemical products by using renewable raw materials is one of the topical areas of medicinal chemistry. The paper presents the synthesis of (2aR,2a1S,5aR,9bR)-4-isopropyl-7,8-dimethoxy-2a1-methyl-2,2a,2a1,3,5a,9b-hexahydrofluoreno[9,1-bc]furan. The title compound was obtained through Prins–Friedel–Crafts cascade reactions of trans-4-hydroxymethyl-2-carene, which was synthesized from 3-carene, one of the main components of gum turpentine. The product yield after purification was 48%. The compound’s structure was confirmed by X-ray diffraction analysis.
]]>Molbank doi: 10.3390/M1733
Authors: Lorenza Romagnoli Andrea D’Annibale Alessandro Latini
Viologens are a highly advantageous class of compounds for the synthesis of functional materials. Owing to their versatile structure, they can embed additional conjugated moieties, thus representing a convenient platform, for example for organic semiconductors and other energy-related uses. A straightforward synthesis of an extended viologen containing a bithiophene is described here, together with its UV-visible absorption and fluorescence spectroscopy, showing multiple absorption and emission bands. Thanks to its ease of synthesis and optical properties, this organic salt appears to be of potential interest for various optoelectronic applications.
]]>Molbank doi: 10.3390/M1732
Authors: Loubna Mokhi Karim Chkirate Xiaodong Zhang Mohsine Driowya Khalid Bougrin
A novel single crystal of (3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl)methyl benzenesulfonate has been synthetized via a one-pot sequential strategy under sonication. The single crystal has been investigated using X-ray diffraction analysis. Hydrogen bonding between C–H···O and C–H···N produces a layer structure in the crystal. According to a Hirshfeld surface analysis, interactions H···H (28.9%), H···O/O···H (26.7%) and H···C/C···H (15.8%) make the largest contributions to crystal packing. The optimized structure and the solid-state structure that was obtained through experiments are compared using density functional theory at the B3LYP/6-311 G + (d,p) level. The computed energy difference between the lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) is 4.6548 eV.
]]>Molbank doi: 10.3390/M1731
Authors: R. Alan Aitken Alexandra H. Campbell Chloé E. Fletcher Alexandra M. Z. Slawin
The X-ray structure of the title compound, formed at low conversion in the reaction of thiosalicylic acid with thionyl chloride, has been determined. The acid chloride groups are oriented to permit an attractive non-bonding O…S interaction. Mechanisms are suggested for the formation of this unexpected product. 1H and 13C NMR data are also reported for the first time for the major reaction product, 2-mercaptobenzoyl chloride.
]]>Molbank doi: 10.3390/M1730
Authors: Tiffany H. Li Lucas C. Messer Nathan J. Weeks Timothy J. Fuhrer Scott T. Iacono
The title compound was synthesized in near quantitative yields via initial nucleophilic aromatic substitution of pentafluoropyridine (PFP) with 4-(2-bromoethyl)phenol as a versatile precursor for ionic liquids (ILs). The purity and structure were determined using 1H, 13C, and 19F NMR and GC-EIMS.
]]>Molbank doi: 10.3390/M1729
Authors: R. Alan Aitken David B. Cordes An Jie Ler Aidan P. McKay
The title dibromodisalicylaldehyde, obtained as a by-product in the m-chloroperoxybenzoic acid oxidation of 5-bromo-2-(methoxymethoxy)benzaldehyde, has been characterised by IR and NMR spectroscopy and X-ray diffraction. The structure features two independent molecules with a π–π stacking interaction between them.
]]>Molbank doi: 10.3390/M1728
Authors: R. Alan Aitken David B. Cordes Aidan P. McKay Dheirya K. Sonecha
The X-ray structure of the title compound has been determined for the first time. This features ribbons formed by two parallel chains of molecules joined by C=O···H–N hydrogen bonding, which are then cross-linked by C=O···H–O hydrogen bonds. The structure is compared to those of closely related compounds.
]]>Molbank doi: 10.3390/M1727
Authors: Aleksey A. Vasilev Meglena I. Kandinska Anton Kostadinov Laura Dietz Stanislav Baluschev
The development of new selective fluorogenic probes for monitoring microbiological objects and cellular compartments may help to determine the mechanism of pathogenesis of new pathogens in living cells. The easy and reliable synthetic strategy for the direct preparation of chemically pure styryl dye (E)-3-heptyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide is described. The photophysical properties in different solvents and in water medium neat and in the presence of the dsDNA and RNA of the dye is demonstrated and compared with that of the known structure analogue. The cellular uptake and the ability to bind cell organelles is determined. The introduction of a heptyl substituent attached to the quaternary nitrogen atom of the benzothiazole ring leads to an improvement in the photophysical properties of the dye.
]]>Molbank doi: 10.3390/M1726
Authors: Dayi Liu Régis Guillot Sylvie Robin David J. Aitken
trans-3-Benzyloxycarbonylamino-1-methyl-3-(methylcarbamoyl)azetidine-1-oxide was prepared by stereoselective oxidation of the corresponding azetidine precursor. The stable molecule was characterized in a low-polarity solution by IR, 1H-NMR and 13C-NMR, and in the solid state as a co-crystal with water by X-Ray diffraction. The N-oxide function made a strong intramolecular 7-membered ring hydrogen bond with the methyl amide NH in solution and formed an intermolecular H-bond with the carbamate NH in a neighboring molecule in the solid state.
]]>Molbank doi: 10.3390/M1725
Authors: Rahisa Mohammed Peace Ogadi Dennis M. Seth Amrutaa Vibho Sarah K. Gallant Rory Waterman
2-(((2,7-Dihydroxynaphthalen-1-yl)methylene)amino)-3′,6′-bis(ethylamino)-2′,7′-dimethylspiro[isoindoline-1,9′-xanthen]-3-one was synthesized using Rhodamine 6G hydrazide (prepared using literature methods) and commercially available 2,7-dihydroxynaphthalene-1-carbaldehyde via imine condensation. Structural characterization was performed using FT-IR, 1H-NMR, 13C-NMR, X-ray, and HRMS. This Schiff base shows promise as a ligand for the colorimetric analysis of uranium in water.
]]>Molbank doi: 10.3390/M1724
Authors: Panagiotis Kouvatsis Dimitrios Glykos John C. Plakatouras Gerasimos Malandrinos
A new heteroleptic Cu(I) complex, [Cu(L)(PPh3)2][BF4] (L = 6-(furan-2-yl)-2,2′-bipyridine; PPh3 = triphenylphosphine), was successfully synthesized and characterized. Its molecular structure was determined using X-ray crystallography, and NMR as well as HR-ESI-MS data confirm the compound’s integrity in solution. The complex exhibits emission solely in the solid state (λem = 576 nm) and demonstrates a photoluminescence quantum yield of 2.5%.
]]>Molbank doi: 10.3390/M1723
Authors: Nirmal Kumar Shee Hee-Joon Kim
[Sn(OSO3)2(TPyHP)](HSO4)2∙8H2O (1), an ionic Sn(IV)-porphyrin complex, was prepared by reacting [Sn(OH2)2TPyP] with dilute sulfuric acid. X-ray structural analysis revealed that the zwitterionic [Sn(OSO3)2TPyHP]2+ species consists of two anionic axial Sn–O–SO3 units and four peripheral pyridinium moieties, with an overall dicationic charge balanced by two hydrogen sulfate (HSO4−) counter-anions. Ionic hydrogen bonding between the oxygen atoms of axial sulfato ligands and the peripheral pyridinium groups of adjacent Sn(IV)-porphyrin cations led to the formation of a 1D channel filled with counter-anions and water molecules. The supramolecular self-assembly of 1 was further characterized using various spectroscopic techniques, including 1H NMR spectroscopy, elemental analysis, ESI-mass spectrometry, UV-vis spectroscopy, fluorescence spectroscopy, FT-IR spectroscopy, thermogravimetric analysis (TGA), and powder X-ray diffractometry. The zwitterionic [Sn(OSO3)2TPyHP]2+ complex is a structurally well-defined complementary scaffold involved in supramolecular self-assembly. This novel class of ion-assembled metalloporphyrin is a potential functional porphyrin material used in ion exchange applications.
]]>Molbank doi: 10.3390/M1722
Authors: Thomas Gelbrich Jascha Schinke Ulrich J. Griesser
The two-component compound formed by codeine and cyclopentobarbital was produced using grinding techniques and through evaporation from alcoholic solutions. The cocrystal nature of this phase was established unequivocally through single crystal X-ray structure determination. The asymmetric unit contains one formula unit. In the cyclopentobarbital molecule, the cyclopentenyl ring is disordered over two positions related by a rotation of approximately 180° about its C—C bond to the pyrimidine ring. The two NH groups of the cyclopentobarbital molecule form N—H⋯N and N—H⋯O bonds to piperidine and hydroxyl groups, respectively, belonging to different codeine molecules. In addition, the hydroxyl and methoxy groups of neighboring codeine molecules are linked by O—H⋯O interactions, resulting in a H-bonded framework structure of codeine and cyclopentobarbital molecules. The cocrystal was also characterized using thermal analysis, X-ray powder diffraction and IR spectroscopy.
]]>Molbank doi: 10.3390/M1721
Authors: Yuliya E. Ryzhkova Varvara M. Kalashnikova Fedor V. Ryzhkov Artem N. Fakhrutdinov Michail N. Elinson
Pseudo-multicomponent reactions (Pseudo-MCRs) have led to a variety of compounds with interesting biological properties, especially desirable in the pharmaceutical industry. The isatin nucleus could be considered a privileged scaffold for the design of biologically active substances. Dimedone is an interesting and versatile molecule for most organic transformations, especially one-pot and multicomponent reactions. Xanthene derivatives are still an attractive research field for both academia investigations and industry. In this investigation, a simple and efficient tandem Knoevenagel–Michael protocol with subsequent cyclization for the synthesis of the previously unknown 4a′-hydroxy-3′,3′,5,6′,6′,7-hexamethyl-3′,4′,4a′,6′,7′,9a′-hexahydrospiro[indole-3,9′-xanthene]-1′,2,8′(1H,2′H,5′H)-trione was elaborated. The suggested method is based on the pseudo-MCR of 5,7-dimethylisatin and dimedone. The structure of the earlier unknown compound was proven using 1H, 13C-NMR, and IR spectroscopy, mass spectrometry, and elemental analysis. To compare the developed protocol with the existing ones, unsubstituted spiro[indole-3,9′-xanthene] was synthesized. Its structure has been proven using two-dimensional (2D) NMR spectroscopy techniques.
]]>Molbank doi: 10.3390/M1720
Authors: Bakr F. Abdel-Wahab Ahmed F. Mabied James C. Fettinger Abdelbasset A. Farahat
The reaction of 2-bromo-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (1) with 4-amino-5-((2,4-dichlorophenoxy)methyl)-4H-1,2,4-triazole-3-thiol (2) in absolute ethanol in the presence of triethyl amine as catalyst gave 2-((4-amino-5-((2,4-dichlorophenoxy)methyl)-4H-1,2,4-triazol-3-yl)thio)-1-(5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)ethan-1-one (3) in 73% yield. The structure of the title heterocycle (3) was confirmed by X-ray single crystal diffraction and spectral analyses (NMR and IR).
]]>Molbank doi: 10.3390/M1719
Authors: Mohamed Kdider Catherine Elleouet François Y. Pétillon Philippe Schollhammer
The di-iron carbonyl dithiolene bridged complex [Fe2(CO)6(µ-S2C2(CO2Me)2)] (1) reacts with 1 equivalent of phosphane PR3 (R = Ph, OMe) to give, as major products, monosubstituted derivatives [Fe2(CO)5L(µ-S2C2(CO2Me)2)] (L = PPh3 (2), P(OMe)3 (3)). In the presence of an excess (3–4 equiv.) of P(OMe)3, the cleavage of 1 arises partly and a mixture of the mononuclear species [Fe(CO)(P(OMe)3)2(κ2-S2C2(CO2Me)2)] (4) and 3 is obtained. The compounds 2–4 were analyzed by IR and 1H, 31P-{1H} NMR spectroscopies. Their structures in solid state were determined by X-ray diffraction analyses, which accord with their spectroscopic characteristics.
]]>Molbank doi: 10.3390/M1718
Authors: Luka Ciber Helena Brodnik Franc Požgan Jurij Svete Bogdan Štefane Uroš Grošelj
A monosubstituted benzene-1,2-diamine building block, N1-(3,5-bis(trifluoromethyl)benzyl)benzene-1,2-diamine, was prepared in two steps from commercially available 3,5-bis(trifluoromethyl)benzylamine and 1-fluoro-2-nitrobenzene, while the use of 3,5-bis(trifluoromethyl)aniline as the starting amine gave a triarylamine, N,N-bis(2-nitrophenyl)-3,5-bis(trifluoromethyl)aniline. The structures of the newly synthesized compounds were fully characterized.
]]>Molbank doi: 10.3390/M1717
Authors: Niall Hehir John F. Gallagher
The title compound N-(2,3-difluorophenyl)-2-fluorobenzamide or (Fo23) was obtained at high yield (88%) from the condensation reaction of 2-fluorobenzoyl chloride with 2,3-difluoroaniline using standard synthetic procedures. The crystal structure of Fo23 was determined at 294 (1) K using single crystal X-ray diffraction methods and represents the first regular tri-fluorinated benzamide with formula C13H8F3NO compared to the difluorinated and tetra-fluorinated analogues. In the structure, both aromatic rings are effectively co-planar, with an interplanar angle of 0.5(2)°; however, the central amide group plane is oriented by 23.17(18)° and 23.44(17)° from the aromatic rings as influenced by 1D amide⋯amide hydrogen bonds along the a-axis direction. Longer C-H⋯F/O interactions and the arrangement of a R22(12) synthon involving two C-F, a N-H and two C-H, together with C-F⋯C ring⋯ring stacking contacts, complete the interactions in the Fo23 crystal structure.
]]>Molbank doi: 10.3390/M1716
Authors: Yuhan Xie Houin Kuan Qin Wei Alessandra Gianoncelli Giovanni Ribaudo Paolo Coghi
We herein report the synthesis of a derivative of the natural compound celastrol linked to the antimalarial drug primaquine through an amide obtained by the activation of the carboxylic acid with HOBt/EDC. The chemical structure of the new molecule was fully characterized by proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), heteronuclear single quantum coherence (HSQC), correlation spectroscopy (1H-1H-COSY), distortionless enhancement by polarization transfer (DEPT), mass spectrometry, Fourier-transform infrared (FTIR), and ultraviolet (UV) spectroscopies. Computational studies were enrolled to predict the interaction of the synthesized compound with sarco-endoplasmic reticulum (SR) Ca2+ transport ATPase (SERCA), a target of relevance for developing new therapeutics against arthritis. The drug-likeness of the compound was also investigated by predicting its pharmacokinetic properties.
]]>Molbank doi: 10.3390/M1715
Authors: Beniamin-Nicolae Pintea Ion Burcă Valentin Badea Francisc Peter
The scope of the current work was to synthesize an S-alkylated 1,2,4-triazole-3-thiol derivative. Synthesis was carried out in two steps: in the first step, 4,5-diphenyl-4H-1,2,4-triazole-3-thiol was S-alkylated using a halogenated acetal and cesium carbonate. In the second step, several acetal deprotection procedures were tested, and the aldehyde obtained was isolated as a bisulfite adduct. The structures of the new compounds were characterized by FT-IR, 1D, and 2D NMR spectroscopic methods.
]]>Molbank doi: 10.3390/M1714
Authors: Yuriy A. Kvashnin Pavel A. Slepukhin Denis A. Gazizov Ekaterina F. Zhilina Gennady L. Rusinov Egor V. Verbitskiy Valery N. Charushin
[1,2,5]Oxadiazolo[3,4-b]pyrazines are of great interest due to their promising photophysical and electrochemical properties, as well their potential use in a wide range of electronic devices. Herein, we report on the preparation of the unexpected product derived from the interaction of 2′-([1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl)-N,N-diphenyl-[1,1′-biphenyl]-4-amine with 2-cyanoacetic acid under basic conditions. The resulting product was characterized using 1H and 13C NMR spectra, high resolution mass spectrometry, Fourier-transform infrared spectroscopy (FTIR), and X-ray diffraction analyses. Furthermore, its photophysical and electrochemical properties were studied using cyclic voltammetry, UV–Vis, and emission spectroscopy. The experimental results have been further rationalized through theoretical DFT calculations.
]]>Molbank doi: 10.3390/M1713
Authors: Stephen R. Isbel Alejandro Bugarin
There is a growing interest in developing more efficient synthetic alternatives for the synthesis of nitrogen-containing allylic compounds. This article presents a straightforward two-step protocol to produce 5-(3-azidoprop-1-en-2-yl)benzo[d][1,3]dioxole 4 from the natural product safrole. The method yielded the expected α-azidomethyl styrene 4, in good yield, via a dearomative rearrangement.
]]>Molbank doi: 10.3390/M1712
Authors: Caterina Momoli Valerio Morlacci Marco Chiarini Laura Palombi Antonio Arcadi
To optimize the experimental conditions used for the Friedländer-type condensation, an angular fused 4-substituted quinoline steroid has been obtained in very high yield and regioselectivity using readily available 4-cholesten-3-one and 2′-aminoacetophenone. Moreover, by varying the reaction conditions and the catalyst, the corresponding linear regioisomer was also achieved with an acceptable isolated yield and high chemoselectivity. Both structures have been definitively elucidated via 2D-NMR and fully characterized.
]]>Molbank doi: 10.3390/M1711
Authors: Camila Caro Garrido Tom Leyssens Koen Robeyns
The structure of K5(HPO4)2(H2PO4)·H2O was determined via single crystal diffraction. The crystal structures of phosphate salts of potassium have been known since the early days of crystallography. Here, we present a new monohydrate adduct between K2HPO4 and KH2PO4.
]]>Molbank doi: 10.3390/M1710
Authors: Yiwei Gong Jas S. Ward Kari Rissanen Florian F. Mulks
Site-selective functionalization of pyridines is a crucial tool for the synthesis of diverse pharmaceuticals and materials. We introduced diiminium pyridine adducts as highly convenient and potent Lewis acids. We report that tributylphosphine selectively adds to the 4-position of pyridine in tetramethyldiiminium pyridine ditrifluoromethanesulfonate, resulting in the formation of the title compound. This finding represents an advancement towards the utilization of diiminium units as organic reagents or catalysts for pyridine functionalization. We also employ computational models to determine fluoride and hydride ion affinities, Fukui function f+(r), molecular electrostatic potential, and pKa values, providing valuable insights for future investigations in this area.
]]>Molbank doi: 10.3390/M1709
Authors: Lara Mollà-Guerola Alejandro Baeza
The synthesis of (E)-2-(1,3-diphenylallyl)-3,5-dimethoxyphenol is described by means of the reaction of 3,5-dimethoxyphenol with (E)-1,3-diphenylprop-2-en-1-ol in 1,1,1,3,3,3-hexafluoroispropanol (HFIP), which acts as a solvent and reaction promoter. The reaction proceeds smoothly to afford the mentioned compound in high yield under a metal and additive-free procedure. The corresponding allylated phenol has been fully characterized.
]]>Molbank doi: 10.3390/M1708
Authors: Egar Pamela Lukman Atmaja Mardi Santoso
Isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) was obtained from the 2-methyl-6-nitrobenzoic anhydride (MNBA)/4-dimethylaminopyridine (DMAP)-catalyzed reaction at room temperature for 190 min in dichloromethane with a yield of 95%. The structure of isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) was elucidated using NMR, FTIR, and high-resolution mass spectrometry. In vitro sun protection factor evaluation exhibited a value of 37.10 ± 0.03 which indicates that isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate (1) is a sunscreen agent with high protection.
]]>Molbank doi: 10.3390/M1707
Authors: Anna A. Smirnova Liana M. Zakirova Irina E. Smirnova Elena V. Tretyakova
Novel diterpenic peptide derivatives were synthesized via the Ugi four-component reaction at ambient temperature. The protocol employed a reaction between formaldehyde, benzyl amine, the corresponding diterpene acid, and ethyl 2-isocyanoacetate. The anticancer properties of the compounds were studied in vitro.
]]>Molbank doi: 10.3390/M1706
Authors: Ersya Yanu Ramadhani Nur Pasca Aijijiyah Eko Santoso Lukman Atmaja Mardi Santoso
N′-(5-bromofuran-2-carbonyl)isonicotinohydrazide (1) was obtained in the form of a colorless solid from the 2-methyl-6-nitrobenzoic anhydride (MNBA)/4-dimethylaminopyridine (DMAP)-catalyzed reaction of 5-bromofuran-2-carboxylic acid and isoniazid in dichloromethane at room temperature with a yield of 83%. The structure of N′-(5-bromofuran-2-carbonyl)isonicotinohydrazide (1) was elucidated using 1H NMR, 13C NMR, FTIR, and high-resolution mass spectrometry. Molecular docking screening of the title compound (1) on cyclooxygenase-2 (COX-2) protein (PDB ID: 5IKR) indicated that compound (1) has a good binding affinity, suggesting that further structure optimization and in-depth research can be carried out on compound (1) as a potential COX-2 inhibitor.
]]>Molbank doi: 10.3390/M1705
Authors: Ion Burcă Valentin Badea Calin Deleanu Vasile-Nicolae Bercean Francisc Péter
A new triazol-3-one resulted unexpectedly from the reduction reaction of a heterocyclic thioketone using sodium borohydride in pyridine containing a small amount of water. The structure of the new compound was characterised using FT-IR, 1D and 2D NMR, and HRMS spectroscopic methods.
]]>Molbank doi: 10.3390/M1704
Authors: Liliya E. Nikitina Ilmir R. Gilfanov Roman S. Pavelyev Svetlana A. Lisovskaya Elena Y. Trizna Ilfat Z. Rakhmatullin Vladimir V. Klochkov Rustam R. Davletshin Olga B. Babaeva Alena I. Kolesnikova Olga V. Ostolopovskaya Larisa L. Frolova Airat R. Kayumov
The syntheses of the title compounds were performed using lauric and myristic acids. The compounds obtained were characterized using 1H-, 13C-NMR and 2D 1H-1H COSY, 1H-13C HSQC NMR, IR, and high-resolution mass spectrometry. Both compounds exhibited bactericidal activity on S. aureus comparable to that of a reference drug (miramistin). Compound 10, with lauric acid fragment, had a 16-fold higher activity on P. aeruginosa compared to compound 11, which in turn contains myristic acid fragment (with minimum inhibitory concentrations of 32 and 512 μg/mL, respectively). Compound 11 exhibited a pronounced activity against all types of fungi (higher than the activity of miramistin), while the activity of compound 10 was considerably lower. Thus, compound 11 can serve as a promising antimicrobial agent for the treatment of various fungal and staphylococcal infections, while compound 10 is of interest to treat P. aeruginosa-associated infections.
]]>Molbank doi: 10.3390/M1703
Authors: Enrico Podda Massimiliano Arca Anna Pintus Vito Lippolis Giulio Ferino James B. Orton Simon J. Coles Maria Carla Aragoni
2,7-Bis(pyridin-4-ylethynyl)-9H-carbazole (1) was synthesized by reacting 4-ethynylpyridine hydrochloride with 2,7-dibromo-9H-carbazole. The full characterization of compound 1 is presented, and the crystal structure of its monohydrate was determined by single-crystal XRD analysis.
]]>Molbank doi: 10.3390/M1702
Authors: Olga I. Adaeva Dmitry V. Demchuk Victor V. Semenov
This article presents a novel approach for synthesizing a new 5,8-dimethoxy derivative of esculetin via the selective cleavage of the methylene bridge in sabandin—naturally occurring and easily synthetically accessible methoxylated coumarin. A high selectivity is achieved by using acetoxylation of methylenedioxy group with lead tetraacetate. Natural coumarin sabandin as a starting compound was prepared in a few simple steps from 5-allyl-4,7-dimethoxybenzo[d][1,3]dioxole (apiol), which is readily available from parsley and dill seed extracts. The developed method enables an efficient and straightforward synthesis of a new derivative of esculetin with potential medicinal and therapeutic applications.
]]>Molbank doi: 10.3390/M1701
Authors: Ion Burcă Alexandra-Mihaela Diaconescu Valentin Badea Francisc Péter
A new azo compound was synthesized via an azo coupling reaction between 4-(phenyldiazenyl)benzenediazonium chloride and 8-hydroxyquinoline (8-Hq). The new diazene compound can be used to synthesize metal complexes as a derivative of 8-Hq. The structure of the new compound was characterized using UV–Vis, FT-IR, and 2D NMR spectroscopic methods.
]]>Molbank doi: 10.3390/M1700
Authors: Natalia V. Obruchnikova Oleg A. Rakitin
1,2,5-Oxadiazol-3-amines with a heterocyclic substituent in the 4-position are being intensively investigated as compounds with valuable pharmacological activity. In this communication, the reaction of 1,2,5-oxadiazole-3,4-diamine with 2,5-hexanedione was shown to selectively give 4-(2,5-dimethyl-1H-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine as a product of the Paal–Knorr reaction. The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, 1H and 13C NMR, and IR spectroscopy.
]]>Molbank doi: 10.3390/M1699
Authors: R. Alan Aitken Lynn A. Power Alexandra M. Z. Slawin
The product formed by base-induced dimerisation of (2S,5S)-2-tert-butyl-5-methyl-1,3-dioxolan-4-one is shown by X-ray diffraction to be the title compound and not the isomeric fused-ring 1,3-dioxolane/1,3-dioxane-4-one structure proposed by previous researchers. The analogous compound derived from (2S,5S)-5-benzyl-2-tert-butyl-1,3-dioxolan-4-one has also been obtained and characterised.
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