- Synthesis of novel amides with antiradical capacity from 2-mercaptobenzimidazole and cinnamic acids: Evaluation through donor-acceptor maps and QSAR
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The structures of thioethers I-III and the new amidic compounds 1(a-f)-3(a-f) derived from 2-mercaptobenzimidazole (MBZ) and cinnamic acids were confirmed by NMR and elemental analysis. Antioxidant activity was evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH●) radical scavenging assay and 2,2-azinobis (3-ethyl benzothiazoline-6-sulfonic acid) ABTS●+ radical cation decolorization method. Besides, donor-acceptor maps (DAM) and electrophilicity were calculated using DFT/B3LYP method with a 6-311G(d,p) basis set. MBZ, I-III and (1a-3a) compounds showed higher activity in vitro antioxidant assays, confirming with in silico studies that they are the best candidates. The findings found in antiradical activity suggest that these compounds could be promising in the development of new antitumor and antimicrobial agents. QSAR Molecular properties and topological descriptors of the synthesized compounds 1(a-f)-3(a-f) were calculated. The QSAR model indicates that the size and molecular shape are relevant for the antiradical activity for this family of compounds.
- Benicio, Fernando Obledo,Gami?o, José Antonio Valcárcel,Hernández, Carlos Eduardo Macías,Martínez, Francisco J. Martínez,Martínez, María Teresa Sumaya,Ramos-Organillo, ángel,Rodríguez, Omar Alejandro Ramos,Sánchez, Juan Pablo Mojica,Sandoval, Zeferino Gómez
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- 2-Mercaptobenzimidazole derivatives as novel butyrylcholinesterase inhibitors: Biology-oriented drug synthesis (BIODS), in-vitro and in-silico evaluation
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Schiff bases gaining remarkable importance day by day in the current situation Schiff bases are found to be a valuable pharmacophore for the synthesis and development of various biologically active heterocyclic compounds. In recent past, we have reported various classes of compounds as enzyme inhibitors, in continuation; A series of 2-Mercaptobenzimidazole hydrazone derivatives (9-42) were synthesized through multistep reactions in high yields and evaluated for butyrylcholinesterase inhibition. In present study, 2-ethylthio benzimidazole was formed by the reaction of 2-Mercaptobenzimidazole with bromoethane. In the second step (2-(2-(ethylthio)benzimidazolyl)acetate) obtained by the reaction of 2-ethylthio benzimidazole with ethyl chloroacetate. In the third step, 2-(2-(ethylthio)benzimidazolyl)acetate was refluxed in methanol with hydrazine hydrate and get 2-((ethylthio)benzimidazolyl)acetohyrazide. In the last step, 2-((ethylthio)benzimidazolyl)acetohyrazide was reacted with different aldehydes in the presence of glacial acetic acid (catalyst) to get a series of 2-Mercaptobenzimidazole hydrazone derivatives. Product was characterized by 1H NMR and 13C NMR. These newly synthesized compounds showed varying degree of butyrylcholinesterase inhibition. Compound no. 15 with (IC50 = 25.10 ± 0.90 μM) was found to be most active in the whole series. Similarly, compounds 42, 12, 40, 17, 22, 28 and 09 exhibited excellent activity with IC50 values are (IC50 = 25.36 ± 0.57 μM, IC50 = 27.30 ± 0.52 μM, IC50 = 34.31 ± 0.59 μM, IC50 = 51.29 ± 0.64 μM, IC50 = 54.52 ± 0.95 μM, IC50 = 57.90 ± 0.45 μM and IC50 = 60.93 ±0.67 μM) respectively as compared to standard galantamine 18.13±0.20 μM. Molecular docking helped to find interactions between butyrylcholinesterase enzyme and test compounds. This study results that Schiff bases have been discovered a new class of butyrylcholinesterase inhibitors which have not been discovered earlier.
- Yousaf, Muhammad,Khan, Momin,Ali, Mumtaz,Wadood, Abdul,Rehman, Ashfaq Ur,Jan, Muhammad Saeed,Sadiq, Abdul,Alam, Faima
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p. 263 - 273
(2021/01/20)
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- Highly efficient tandem syntheses of unsymmetrically substituted isomeric S,N-disubstituted-2-mercaptobenzimidazoles
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Highly efficient tandem syntheses of unsymmetrically substituted isomeric S,N-disubstituted-2-mercaptobenzimidazoles have been developed. The structures of 6a-d and isomeric compounds 9a-d have been synthesized from 2-mercaptobenzimidazole using tandem synthesis. The structures of 6a-d and isomeric compounds 9a-d have been established by spectral and analytical data, and by unambiguous syntheses.
- Rao, S. Srinivas,Reddy, Ch Venkata Ramana,Dubey
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p. 829 - 832
(2015/06/30)
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- Alkylation and Aminomethylation of 1,3-Dihydro-2H-Benzimidazole-2-Thione
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Alkylation of 1,3-dihydro-2H-benzimidazole-2-thione (2-mercaptobenzimidazole) with bromoethane and chloroacetic acid derivatives occurrs at the sulfur atom, leading to the corresponding 2-sulfanylbenz-imidazole derivatives. Aminomethylation of 1,3-dihydro-2H-benzimidazole-2-thione with piperidine and 4-methylpiperidine gives reaction products at both nitrogen atoms, while reaction with morpholine gives derivative at only one nitrogen atom, which is in an equilibrium with the starting compound and bis-adduct in DMSO solution.
- Bespalov,Gorchakova,Ivanov,Kuznetsov,Kuznetsova,Pankova,Prokopenko,Avdontceva
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p. 1547 - 1558
(2015/02/19)
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- Synthesis and preliminary evaluation of benzimidazole derivatives as antimicrobial agents
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A series of 2-alkylsulphanylbenzimidazoles was synthesised and the compounds were evaluated for their in vitro antimicrobial activity. The structures of the compounds were confirmed by 1H-NMR and IR data, and their purity by elemental analysis. Antimycobacterial activities against Mycobacterium tuberculosis and non-tuberculous mycobacteria as well as antifungal activities against Candida albicans, Candida tropicalis, Candida krusei, Candida glabrata, Trichosporon beigelii, Trichophyton mentagrophytes and Aspergillus fumigatus were expressed as the corresponding MIC values. The substances exhibited appreciable antimycobacterial activity, in particular, against non-tuberculous mycobacteria. The activity of the most active compound in the set, 3,5-dinitro derivative 4t, exceeded that of the standard isoniazide against M. kansasii and M. avium. The antifungal activities of the compounds were relatively low. A weak antifungal effect was observed against the dermatophyte Trichophyton mentagrophytes. None of the compounds showed significant inhibitory activity against yeasts.
- Klimesova, Vera,Koci, Jan,Pour, Milan,Stachel, Jiri,Waisser, Karel,Kaustova, Jarmila
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p. 409 - 418
(2007/10/03)
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- REACTIONS OF 1-VINYLBENZIMIDAZOLE-2-THIONE WITH ALCOHOLS AND PHENOL
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1-(α-Alkoxyethyl)- and 1-(α-phenoxyethyl)benzimidazole-2-thiones were obtained in the reaction of 1-vinylbenzimidazole-2-thione with alcohols and phenol in the presence of gaseous hydrogen chloride.It was established that partial hydrolysis of the 1-(α-alkoxyethyl)benzimidazole-2-thiones to benzimidazole-2-thione with subsequent alkylation with excess alcohol at the exocyclic sulfur atom occurs under the conditions of the investigated reaction.A convenient method for the alkylation of thiones was proposed, and a number of 2-alkylthiobenzimidazoles were synthesized.
- Abramova, N. D.,Skvortsova, G. G.,Trzhtsinskaya, B. V.
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p. 656 - 658
(2007/10/02)
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