Design, Synthesis and in Vitro Antibacterial Activity of 2-thiomethyl-benzimidazole Derivatives
Open Access
- 1 January 2021
- journal article
- research article
- Published by Scientific Research Publishing, Inc. in Advances in Biological Chemistry
- Vol. 11 (04), 165-177
- https://doi.org/10.4236/abc.2021.114012
Abstract
A series of novel substituted benzimidazole (7a - n) derivatives were synthesized and characterized by 1H, 13C Nuclear Magnetic Resonance (NMR) spectra and High Resolution Mass Spectrometry (HRMS). The substitution was done in position -1 and -2 by appropriate groups. These compounds are obtained by N-alkylation reaction with thiomethyl-1H-benzimidazole intermediates (5a - g). Design of intermediates (5a - g) was made by condensation reaction between 2-methylbenzimidazole thiourunium salt (3) and functionalized halides (4) in the presence of sodium hydroxide (NaOH). Among the twenty-one compounds synthesized, ten were evaluated for their antimicrobial activity on three bacterial strains namely: Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and Pseudomonas aeruginosa ATCC 27853. Only E. coli ATTC 25922 was susceptible to the synthesized derivatives 5g, 7f and 7h with a significant antibacterial activity (CMI is between 250 and 500 μg/mL).Keywords
This publication has 20 references indexed in Scilit:
- Synthesis and biological evaluation of 2-substituted benzimidazole derivativesArabian Journal of Chemistry, 2015
- In-vivo analgesic and anti-inflammatory activities of newly synthesized benzimidazole derivativesEuropean Journal of Medicinal Chemistry, 2010
- Synthesis, physicochemical properties and antimicrobial activity of some new benzimidazole derivativesEuropean Journal of Medicinal Chemistry, 2009
- Apoptosis induced by 2-acetyl-3-(6-methoxybenzothiazo)-2-yl-amino-acrylonitrile in human leukemia cells involves ROS-mitochondrial mediated death signaling and activation of p38 MAPKCancer Letters, 2009
- Convenient one-pot synthesis of novel 2-substituted benzimidazoles, tetrahydrobenzimidazoles and imidazoles and evaluation of their in vitro antibacterial and antifungal activitiesEuropean Journal of Medicinal Chemistry, 2009
- N-Acylated and N,N′-diacylated imidazolidine-2-thione derivatives and N,N′-diacylated tetrahydropyrimidine-2(1H)-thione analogues: Synthesis and antiproliferative activityEuropean Journal of Medicinal Chemistry, 2009
- Synthesis, anti-bacterial, anti-asthmatic and anti-diabetic activities of novel N-substituted-2-(4-phenylethynyl-phenyl)-1H-benzimidazoles and N-substituted 2[4-(4,4-dimethyl-thiochroman-6-yl-ethynyl)-phenyl)-1H-benzimidazolesEuropean Journal of Medicinal Chemistry, 2008
- Synthesis, anti-bacterial, anti-asthmatic and anti-diabetic activities of novelN-substituted-2-(benzo[d]isoxazol-3-ylmethyl)-1H-benzimidazolesJournal of Heterocyclic Chemistry, 2007
- Microwave Activated Solid Support Synthesis of New Antibacterial QuinolonesMonatshefte für Chemie / Chemical Monthly, 2000
- Synthesis and biological evaluation of novel 2′-deoxy-4′-thio-imidazole nucleosidesBioorganic & Medicinal Chemistry, 1999