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

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5 pages, 1047 KiB  
Short Note
N-(9,10-Dioxo-9,10-dihydroanthracen-1-yl)-2-methylbenzamide
by Hamad H. Al Mamari and Ahmed Al Sheidi
Molbank 2020, 2020(4), M1175; https://0-doi-org.brum.beds.ac.uk/10.3390/M1175 - 04 Dec 2020
Cited by 1 | Viewed by 2148
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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5 pages, 773 KiB  
Short Note
6,6′-{[Ethane-1,2-diylbis(azaneylylidene)]bis(methaneylylidene)}bis[2-(hexyloxy)phenolato] Nickel(II)
by Daniil A. Lukyanov, Anna S. Borisova and Oleg V. Levin
Molbank 2020, 2020(4), M1174; https://0-doi-org.brum.beds.ac.uk/10.3390/M1174 - 03 Dec 2020
Viewed by 2293
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
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9 pages, 1208 KiB  
Communication
Synthesis of 3-Trifluoromethyl-5,6-dihydro-[1,2,4]triazolo Pyrazine Derivatives and Their Anti-Cancer Studies
by Rajaiah Raveesha, Malavalli Guruswamy Dileep Kumar and Salekoppal Boregowda Benaka Prasad
Molbank 2020, 2020(4), M1173; https://0-doi-org.brum.beds.ac.uk/10.3390/M1173 - 02 Dec 2020
Cited by 1 | Viewed by 3065
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)
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3 pages, 159 KiB  
Editorial
Editorial: Special Issue “Molecules from Side Reactions”
by Stefano D’Errico
Molbank 2020, 2020(4), M1172; https://0-doi-org.brum.beds.ac.uk/10.3390/M1172 - 30 Nov 2020
Viewed by 1649
Abstract
Organic synthesis is a powerful tool that allows researchers to express their scientific creativity [...] Full article
(This article belongs to the Collection Molecules from Side Reactions)
3 pages, 442 KiB  
Short Note
N-(2-(1H-indol-3-yl)ethyl)-2-(6-chloro-9H-carbazol-2-yl)propanamide
by Stanimir Manolov, Iliyan Ivanov and Dimitar Bojilov
Molbank 2020, 2020(4), M1171; https://0-doi-org.brum.beds.ac.uk/10.3390/M1171 - 24 Nov 2020
Viewed by 2100
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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6 pages, 1458 KiB  
Short Note
Poly[1,3-Dimethyltetrahydropyrimidin-2(1H)-iminium [tri-µ2-cyanido-κ6C:N-dicuprate(I)]]
by Peter W. R. Corfield and Joseph R. Dayrit
Molbank 2020, 2020(4), M1170; https://0-doi-org.brum.beds.ac.uk/10.3390/M1170 - 24 Nov 2020
Cited by 2 | Viewed by 2240
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 Collection Molecules from Side Reactions)
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4 pages, 1659 KiB  
Short Note
4,4′-(Pyrrolo[3,2-b]pyrrole-1,4-diyl)dianiline
by Lorenza Giordano, Rafael Ballesteros and Rafael Ballesteros-Garrido
Molbank 2020, 2020(4), M1169; https://0-doi-org.brum.beds.ac.uk/10.3390/M1169 - 23 Nov 2020
Cited by 2 | Viewed by 2140
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 Collection Heterocycle Reactions)
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Scheme 1

7 pages, 484 KiB  
Short Note
6-Nitro-7-tosylquinazolin-4(3H)-one
by Thi Ngoc Nguyen, Thi Phuong Thuy Tran, Thi Hoang Mai Vu, Hoa Binh Nguyen, Nguyet Suong Huyen Dao, Van Giang Nguyen, Dinh Luyen Nguyen, Nguyen Trieu Trinh and Van Hai Nguyen
Molbank 2020, 2020(4), M1168; https://0-doi-org.brum.beds.ac.uk/10.3390/M1168 - 21 Nov 2020
Viewed by 2721
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 Collection Heterocycle Reactions)
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Graphical abstract

11 pages, 2435 KiB  
Short Note
Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate
by Serigne Abdou Khadir Fall, Saïd Achamlale, Younas Aouine, Asmae Nakkabi, Hassane Faraj and Anouar Alami
Molbank 2020, 2020(4), M1167; https://0-doi-org.brum.beds.ac.uk/10.3390/M1167 - 20 Nov 2020
Cited by 2 | Viewed by 2457
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)
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5 pages, 745 KiB  
Short Note
Ethyl (S)-2-Benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate
by Mario A. Leyva-Acuña, Francisco Delgado-Vargas, Gabriela López-Angulo and Julio Montes-Avila
Molbank 2020, 2020(4), M1166; https://0-doi-org.brum.beds.ac.uk/10.3390/M1166 - 13 Nov 2020
Viewed by 2279
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 Collection Heterocycle Reactions)
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Scheme 1

5 pages, 698 KiB  
Short Note
4,6-Dinitro-7-(thiazol-2-ylamino)benzo[c][1,2,5]oxadiazole 1-oxide
by Gabriele Micheletti, Dario Telese and Carla Boga
Molbank 2020, 2020(4), M1165; https://0-doi-org.brum.beds.ac.uk/10.3390/M1165 - 29 Oct 2020
Cited by 1 | Viewed by 2270
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
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Figure 1

5 pages, 866 KiB  
Short Note
2-Propyl-N′-[1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]pentanehydrazide
by Mariia Nesterkina, Dmytro Barbalat, Ildar Rakipov and Iryna Kravchenko
Molbank 2020, 2020(4), M1164; https://0-doi-org.brum.beds.ac.uk/10.3390/M1164 - 26 Oct 2020
Cited by 1 | Viewed by 2187
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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Graphical abstract

7 pages, 1311 KiB  
Short Note
4,4-Bis(hydroxymethyl)-2-phenyl-2-oxazoline
by Sara Hajib, Salaheddine Boukhssas, Younas Aouine, Anouar Alami, Hassane Faraj, Hafid Zouihri, Brahim El Bali and Mohammed Lachkar
Molbank 2020, 2020(4), M1163; https://0-doi-org.brum.beds.ac.uk/10.3390/M1163 - 21 Oct 2020
Cited by 1 | Viewed by 2396
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)
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Figure 1

4 pages, 358 KiB  
Short Note
(7E)-3-(4-Methoxyphenyl)-7-[(4-methoxyphenyl)methylidene]-4,5,6,7-tetrahydro-3aH-indazole
by Hariyanti Hariyanti, Arry Yanuar, Kusmardi Kusmardi and Hayun Hayun
Molbank 2020, 2020(4), M1162; https://0-doi-org.brum.beds.ac.uk/10.3390/M1162 - 21 Oct 2020
Cited by 1 | Viewed by 2166
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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Graphical abstract

7 pages, 1370 KiB  
Short Note
6-Bromo-N-(3-(difluoromethyl)phenyl)quinolin-4-amine
by Christopher R. M. Asquith and Graham J. Tizzard
Molbank 2020, 2020(4), M1161; https://0-doi-org.brum.beds.ac.uk/10.3390/M1161 - 20 Oct 2020
Cited by 1 | Viewed by 2808
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
(This article belongs to the Special Issue Nitrogen-Containing Molecules: Natural and Synthetic Products Including Coordination Compounds)
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Graphical abstract

4 pages, 524 KiB  
Short Note
Di(bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)dimethylsilane
by Konstantin S. Levchenko, Gregory E. Adamov, Dmitri Yu. Demin, Polina A. Chicheva, Konstantin A. Chudov, Pavel S. Shmelin and Evgeny P. Grebennikov
Molbank 2020, 2020(4), M1160; https://0-doi-org.brum.beds.ac.uk/10.3390/M1160 - 12 Oct 2020
Cited by 1 | Viewed by 2237
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)
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Figure 1

6 pages, 756 KiB  
Short Note
3,5-Bis((E)-4-methoxybenzylidene)-1-(2-morpholinoethyl)piperidin-4-one
by Tyas Kuswardani, Noval Herfindo, Neni Frimayanti, Rudi Hendra and Adel Zamri
Molbank 2020, 2020(4), M1159; https://0-doi-org.brum.beds.ac.uk/10.3390/M1159 - 08 Oct 2020
Cited by 1 | Viewed by 2692
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)
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Figure 1

4 pages, 324 KiB  
Short Note
3-Hydroxy-2-iodophenyl-(4-methylbenzenesulfonate)
by Feng Pan, Yi Guo, Jinying Shen, Xiaofeng Pan, Binbin Hu, Weixin Zheng, Jacques Maddaluno and Muriel Durandetti
Molbank 2020, 2020(4), M1158; https://0-doi-org.brum.beds.ac.uk/10.3390/M1158 - 06 Oct 2020
Cited by 1 | Viewed by 2239
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)
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Scheme 1

5 pages, 4534 KiB  
Short Note
3-Hydroxy-8,14-secogammacera-7,14-dien-21-one: A New Onoceranoid Triterpenes from Lansium domesticum Corr. cv kokossan
by Zulfikar, Nurul Kamila Putri, Sofa Fajriah, Muhammad Yusuf, Rani Maharani, Jamaludin Al Anshori, Unang Supratman and Tri Mayanti
Molbank 2020, 2020(4), M1157; https://0-doi-org.brum.beds.ac.uk/10.3390/M1157 - 30 Sep 2020
Cited by 11 | Viewed by 2906
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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