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Molbank, Volume 2020, Issue 4 (December 2020) – 19 articles

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Open AccessShort Note
N-(9,10-Dioxo-9,10-dihydroanthracen-1-yl)-2-methylbenzamide
Molbank 2020, 2020(4), M1175; https://0-doi-org.brum.beds.ac.uk/10.3390/M1175 - 04 Dec 2020
Viewed by 452
Abstract
In the present Short Note, we report a synthesis for the title compound, N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-2-methylbenzamide by reacting 2-methylbenzoyl chloride (or 2-methylbenzoic acid) with 1-aminoanthraquinone. The synthesized target compound was fully characterized by various spectroscopic methods (1H-NMR, 13C-NMR, IR, GC-MS). The [...] Read more.
In the present Short Note, we report a synthesis for the title compound, N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-2-methylbenzamide by reacting 2-methylbenzoyl chloride (or 2-methylbenzoic acid) with 1-aminoanthraquinone. The synthesized target compound was fully characterized by various spectroscopic methods (1H-NMR, 13C-NMR, IR, GC-MS). The importance of this compound lies its possession of an N,O-bidentate directing group, potentially suitable for metal-catalyzed C-H bond functionalization reactions. Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note
6,6′-{[Ethane-1,2-diylbis(azaneylylidene)]bis(methaneylylidene)}bis[2-(hexyloxy)phenolato] Nickel(II)
Molbank 2020, 2020(4), M1174; https://0-doi-org.brum.beds.ac.uk/10.3390/M1174 - 03 Dec 2020
Viewed by 552
Abstract
Polymeric nickel complexes of salen ligands meet a wide range of applications in catalysis and electrochemistry. Because these polymers usually form very rigid films, the introduction of the conformationally flexible fragments in the corresponding monomers favors the amorphization and, thus, the mass transport. [...] Read more.
Polymeric nickel complexes of salen ligands meet a wide range of applications in catalysis and electrochemistry. Because these polymers usually form very rigid films, the introduction of the conformationally flexible fragments in the corresponding monomers favors the amorphization and, thus, the mass transport. Herein we report a preparation of the hexyloxy-substituted monomeric NiSalen complex by the direct alkylation of the hydroxy-substituted complex. The resulting product was characterized by the 1H and 13C nuclear magnetic resonance (NMR), ESI-high resolution mass spectrometry (ESI-HRMS, and Fourier-transform infrared spectroscopy (FTIR). The crystal structure of the product was examined by an XRD, indicating the formation of the solvate with dichloromethane. The obtained product was found to be highly soluble in non-polar solvents, in contrast to typical NiSalens. Full article
Open AccessCommunication
Synthesis of 3-Trifluoromethyl-5,6-dihydro-[1,2,4]triazolo Pyrazine Derivatives and Their Anti-Cancer Studies
Molbank 2020, 2020(4), M1173; https://0-doi-org.brum.beds.ac.uk/10.3390/M1173 - 02 Dec 2020
Viewed by 406
Abstract
The synthesis of a wide variety of 3-trifluoromethyl-5,6-dihydro-[1,2,4]triazolo pyrazine derivatives, by the treatment of 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride with an array of isocyanates in the presence of triethylamine, is reported. All the target compounds were synthesized in excellent yields under mild reaction conditions. The target [...] Read more.
The synthesis of a wide variety of 3-trifluoromethyl-5,6-dihydro-[1,2,4]triazolo pyrazine derivatives, by the treatment of 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride with an array of isocyanates in the presence of triethylamine, is reported. All the target compounds were synthesized in excellent yields under mild reaction conditions. The target molecules were effectively screened for their anti-cancer properties and the results are promising. The resultant compounds were assessed for their antiproliferative action against two human colon cancer cell lines (HCT-116 and HT-29 colon cancer cell lines). The IC50 range was estimated at 6.587 to 11.10 µM showing that compound RB7 had remarkable anticancer movement on HT-29. Additionally, it was discovered that RB7 incited the mitochondrial apoptotic pathway by up-regulating Bax and down-regulating Bcl2, eventually leading to the activation of Caspase 3 in HT-29 cells and initiation of cell death via the mitochondrial apoptotic pathway. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessEditorial
Editorial: Special Issue “Molecules from Side Reactions”
Molbank 2020, 2020(4), M1172; https://0-doi-org.brum.beds.ac.uk/10.3390/M1172 - 30 Nov 2020
Viewed by 403
Abstract
Organic synthesis is a powerful tool that allows researchers to express their scientific creativity [...] Full article
(This article belongs to the Special Issue Molecules from Side Reactions) Printed Edition available
Open AccessShort Note
N-(2-(1H-indol-3-yl)ethyl)-2-(6-chloro-9H-carbazol-2-yl)propanamide
Molbank 2020, 2020(4), M1171; https://0-doi-org.brum.beds.ac.uk/10.3390/M1171 - 24 Nov 2020
Viewed by 519
Abstract
The titular compound was prepared by a reaction between tryptamine and carprofen, applying, as a “dehydrating” reagent, N,N’-dicyclohexylcarbodiimide. The newly synthesized compound was fully analyzed and characterized via 1H, 13C-NMR, UV, IR, and mass spectral data. Full article
(This article belongs to the Section Structure Determination)
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Open AccessShort Note
Poly[1,3-Dimethyltetrahydropyrimidin-2(1H)-iminium [tri-µ2-cyanido-κ6C:N-dicuprate(I)]]
Molbank 2020, 2020(4), M1170; https://0-doi-org.brum.beds.ac.uk/10.3390/M1170 - 24 Nov 2020
Cited by 1 | Viewed by 504
Abstract
The title compound contains a guanidinium cation that was unexpectedly found during X-ray single crystal analysis of a copper(I) cyanide network expected to contain protonated N,N’-dimethyl-1,3-diaminopropane. The cation was presumably formed by reaction of the amine with cyanide ions in [...] Read more.
The title compound contains a guanidinium cation that was unexpectedly found during X-ray single crystal analysis of a copper(I) cyanide network expected to contain protonated N,N’-dimethyl-1,3-diaminopropane. The cation was presumably formed by reaction of the amine with cyanide ions in the aqueous sodium cyanide/copper cyanide mixtures used in the synthesis. The structure of the network solid features the guanidinium cation as a guest in an anionic two-dimensional polymeric framework with stoichiometry Cu2(CN)3. Confirmation of the structure was provided by analytical, thermal gravimetric and infrared data. Full article
(This article belongs to the Special Issue Molecules from Side Reactions) Printed Edition available
Open AccessShort Note
4,4′-(Pyrrolo[3,2-b]pyrrole-1,4-diyl)dianiline
Molbank 2020, 2020(4), M1169; https://0-doi-org.brum.beds.ac.uk/10.3390/M1169 - 23 Nov 2020
Viewed by 439
Abstract
4,4′-(Pyrrolo[3,2-b]pyrrole-1,4-diyl)dianiline was synthesized in one step from benzene-1,4-diamine and ethylene glycol with Pd/Al2O3 and ZnO. The title compound was characterized by means of NMR techniques and HRMS mass spectrometry. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
Open AccessShort Note
6-Nitro-7-tosylquinazolin-4(3H)-one
Molbank 2020, 2020(4), M1168; https://0-doi-org.brum.beds.ac.uk/10.3390/M1168 - 21 Nov 2020
Viewed by 548
Abstract
Sulfones are important building blocks in the construction of biologically active molecules or functional materials. The sulfonyl functional group in sulfones is so versatile that it can act as either a nucleophile, an electrophile, or a radical in different organic reactions. Recently, quinazoline [...] Read more.
Sulfones are important building blocks in the construction of biologically active molecules or functional materials. The sulfonyl functional group in sulfones is so versatile that it can act as either a nucleophile, an electrophile, or a radical in different organic reactions. Recently, quinazoline sulfones have been used to build asymmetrical ether derivatives as inhibitors of signaling pathways governed by tyrosine kinases and the epidermal growth factor-receptor. In this paper, we report a facile synthesis of a novel quinazoline sulfone, 6-nitro-7-tosylquinazolin-4(3H)-one (III), using the modified protocol from 7-chloro-6-nitroquinazolin-4(3H)-one (I) and sodium p-toluenesulfinate (II). The structure of the title compound III was determined using mass-spectrometry, FT-IR, 1H-NMR, 13C-NMR, DEPT, HSQC (Heteronuclear single quantum coherence), HMBC (Heteronuclear Multiple Bond Correlation Spectroscopy) spectroscopies, and PXRD analysis. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
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Open AccessShort Note
Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate
Molbank 2020, 2020(4), M1167; https://0-doi-org.brum.beds.ac.uk/10.3390/M1167 - 20 Nov 2020
Viewed by 481
Abstract
The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. The cyclization reaction by “click chemistry” was carried out [...] Read more.
The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. The cyclization reaction by “click chemistry” was carried out in a water/ethanol solvent mixture (50/50), in the presence of copper sulfate pentahydrate and catalytic sodium ascorbate. The characterization of the structure of the resulting 1,4-regioisomer was performed by 1D and 2D-NMR experiments, infrared spectroscopy, and elemental analysis. Full article
(This article belongs to the collection Molecules from Catalytic Processes)
Open AccessShort Note
Ethyl (S)-2-Benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate
Molbank 2020, 2020(4), M1166; https://0-doi-org.brum.beds.ac.uk/10.3390/M1166 - 13 Nov 2020
Viewed by 554
Abstract
Pyrimidines are compounds with a wide range of biological activities, and the synthesis of pyrimidine derivatives—useful in chemical and medicinal applications—is important in medicinal chemistry. This work shows the synthesis under microwave irradiation of the novel compound ethyl (S)-2-benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate (3 [...] Read more.
Pyrimidines are compounds with a wide range of biological activities, and the synthesis of pyrimidine derivatives—useful in chemical and medicinal applications—is important in medicinal chemistry. This work shows the synthesis under microwave irradiation of the novel compound ethyl (S)-2-benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate (3) from (S)-N-α-benzoyl-l-arginine ethyl ester hydrochloride (1) and acetylacetone (2). Compound 3 was easily purified, obtained in moderate yield (70%), and fully characterized by UV-Vis, FTIR-ATR spectroscopy, 1H-NMR, 13C-NMR, HRMS, and EI-MS. Full article
(This article belongs to the Special Issue Heterocycle Reactions)
Open AccessShort Note
4,6-Dinitro-7-(thiazol-2-ylamino)benzo[c][1,2,5]oxadiazole 1-oxide
Molbank 2020, 2020(4), M1165; https://0-doi-org.brum.beds.ac.uk/10.3390/M1165 - 29 Oct 2020
Viewed by 636
Abstract
4,6-Dinitro-7-(thiazol-2-ylamino)benzo[c][1,2,5]oxadiazole 1-oxide was synthesized by a SNAr reaction between 7-chloro-4,6-dinitrobenzofuroxan and 2-aminothiazole. The structure of the newly synthesized compound (45% yield) was elucidated based on 1H-NMR, 13C-NMR, NOESY-1D, ESI-MS, UV-Vis, and FT-IR techniques. Full article
Open AccessShort Note
2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide
Molbank 2020, 2020(4), M1164; https://0-doi-org.brum.beds.ac.uk/10.3390/M1164 - 26 Oct 2020
Viewed by 520
Abstract
2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide was obtained in 80% yield via the Einhorn variation of the Schotten–Baumann method by (+)-camphor hydrazide condensation with valproic acid (VPA) chloride. The structure of the titled compound was verified by Raman, FTIR, 1H-NMR, and 13C-NMR spectral analysis [...] Read more.
2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide was obtained in 80% yield via the Einhorn variation of the Schotten–Baumann method by (+)-camphor hydrazide condensation with valproic acid (VPA) chloride. The structure of the titled compound was verified by Raman, FTIR, 1H-NMR, and 13C-NMR spectral analysis along with FAB-mass spectrometry. Thermal properties of synthesized derivative were elucidated by DSC and its purity by HPLC. The compound was successfully tested as a potential anticonvulsant agent based on models of chemically- and electrically-induced seizures. Full article
(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)
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Open AccessShort Note
4,4-Bis(hydroxymethyl)-2-phenyl-2-oxazoline
Molbank 2020, 2020(4), M1163; https://0-doi-org.brum.beds.ac.uk/10.3390/M1163 - 21 Oct 2020
Viewed by 591
Abstract
The title compound, 4,4-bis(hydroxymethyl)-2-phenyl-2-oxazoline 2, a well-known substance, was resynthesized in high yields through a conventional method. The structure of compound 2 was characterized for the first time by a single-crystal X-ray structure determination. The compound was further established through NMR spectroscopy [...] Read more.
The title compound, 4,4-bis(hydroxymethyl)-2-phenyl-2-oxazoline 2, a well-known substance, was resynthesized in high yields through a conventional method. The structure of compound 2 was characterized for the first time by a single-crystal X-ray structure determination. The compound was further established through NMR spectroscopy (1D and 2D). In the molecular packing, two molecules of 4,4-bis(hydroxymethyl)-2-phenyl-2-oxazoline interact through H-Bonds to define “dimers” in which phenyl groups interact especially using π…π contact. Full article
(This article belongs to the Section Structure Determination)
Open AccessShort Note
(7E)-3-(4-Methoxyphenyl)-7-[(4-methoxyphenyl)methylidene]-4,5,6,7-tetrahydro-3aH-indazole
Molbank 2020, 2020(4), M1162; https://0-doi-org.brum.beds.ac.uk/10.3390/M1162 - 21 Oct 2020
Viewed by 589
Abstract
Indazole derivatives are well known to have various pharmacological activities. We synthesized a novel derivative of indazole, namely (7E)-3-(4-methoxyphenyl)-7-[(4-methoxyphenyl)methylidene]-4,5,6,7-tetrahydro-3aH-indazole by condensation reaction between 3-(4-methoxyphenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole and 4-methoxy-benzaldehyde in good yield (61%). Full article
(This article belongs to the Section Organic Synthesis)
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Open AccessShort Note
6-Bromo-N-(3-(difluoromethyl)phenyl)quinolin-4-amine
Molbank 2020, 2020(4), M1161; https://0-doi-org.brum.beds.ac.uk/10.3390/M1161 - 20 Oct 2020
Viewed by 640
Abstract
A routine synthesis was performed to furnish the title compound which incorporates a versatile difluoromethyl group on the aniline substitution of a 4-anilinoquinoline kinase inhibitor motif. In addition, the small molecule crystal structure (of the HCl salt) was solved, which uncovered that the [...] Read more.
A routine synthesis was performed to furnish the title compound which incorporates a versatile difluoromethyl group on the aniline substitution of a 4-anilinoquinoline kinase inhibitor motif. In addition, the small molecule crystal structure (of the HCl salt) was solved, which uncovered that the difluoromethyl group was disordered within the packing arrangement and also a 126.08(7)° out of plane character between the respective ring systems within the molecule. The compound was fully characterized with 1H/13C-NMR and high-resolution mass spectra (HRMS), with the procedures described. Full article
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Open AccessShort Note
Di(bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)dimethylsilane
Molbank 2020, 2020(4), M1160; https://0-doi-org.brum.beds.ac.uk/10.3390/M1160 - 12 Oct 2020
Viewed by 579
Abstract
Di(bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)dimethylsilane (DiBCB-DMS) was synthesized as a promising monomer for polymer coating production with good dielectric properties for electronics. DiBCB-DMS was characterized by 1H, 13C NMR, IR, UV/VIS, and HRMS analysis. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessShort Note
3,5-Bis((E)-4-methoxybenzylidene)-1-(2-morpholinoethyl)piperidin-4-one
Molbank 2020, 2020(4), M1159; https://0-doi-org.brum.beds.ac.uk/10.3390/M1159 - 08 Oct 2020
Viewed by 663
Abstract
The 3,5-bis((E)-4-methoxybenzylidene)-1-(2-morpholinoethyl)piperidin-4-one (3) compound was synthesized by a two-step reaction with 92% yield. The chemical structure of compound 3 was confirmed by IR, NMR, and mass spectrometry. The title compound was screened for its anti-dengue activity against DENV2 NS2B-NS3 [...] Read more.
The 3,5-bis((E)-4-methoxybenzylidene)-1-(2-morpholinoethyl)piperidin-4-one (3) compound was synthesized by a two-step reaction with 92% yield. The chemical structure of compound 3 was confirmed by IR, NMR, and mass spectrometry. The title compound was screened for its anti-dengue activity against DENV2 NS2B-NS3 protease and showed 39.09% inhibitory activity at 200 µg/mL. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessShort Note
3-Hydroxy-2-iodophenyl-(4-methylbenzenesulfonate)
Molbank 2020, 2020(4), M1158; https://0-doi-org.brum.beds.ac.uk/10.3390/M1158 - 06 Oct 2020
Viewed by 636
Abstract
3-Hydroxy-2-iodophenyl-(4-methylbenzenesulfonate) was synthesized via a three-step procedure, starting from commercially available resorcinol, with an overall yield of 65%. The structures of the products were determined by 1H and 13C NMR, HRMS and IR. Full article
(This article belongs to the Section Organic Synthesis)
Open AccessShort Note
3-Hydroxy-8,14-secogammacera-7,14-dien-21-one: A New Onoceranoid Triterpenes from Lansium domesticum Corr. cv kokossan
Molbank 2020, 2020(4), M1157; https://0-doi-org.brum.beds.ac.uk/10.3390/M1157 - 30 Sep 2020
Viewed by 636
Abstract
A new onoceranoid triterpenes, namely 3-hydroxy-8,14-secogammacera-7,14-dien-21-one (1), has been isolated from the fruit peels of Lansium domesticum Corr. cv kokossan. The structure of 1 was determined on the basis of spectroscopic data including infrared, 1D and 2D-NMR, as well as [...] Read more.
A new onoceranoid triterpenes, namely 3-hydroxy-8,14-secogammacera-7,14-dien-21-one (1), has been isolated from the fruit peels of Lansium domesticum Corr. cv kokossan. The structure of 1 was determined on the basis of spectroscopic data including infrared, 1D and 2D-NMR, as well as high resolution mass spectroscopy analysis. Compound 1 showed a weak activity against MCF-7 breast cancer cell lines. Full article
(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)
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