Publication detail

A novel synthesis of 2-arylbenzimidazoles in molecular sieves-MeOH system and their antitubercular activity

CHATURVEDI, A. VERMA, A. THAKUR, J. ROY, S. TRIPATHI, S. KUMAR, B. KHWAJA, S. SACHAN, N. SHARMA, A. CHANDA, D. SHANKER, K. SAIKIA, D. NEGI, A.

Original Title

A novel synthesis of 2-arylbenzimidazoles in molecular sieves-MeOH system and their antitubercular activity

English Title

A novel synthesis of 2-arylbenzimidazoles in molecular sieves-MeOH system and their antitubercular activity

Type

journal article in Web of Science

Language

en

Original Abstract

Arylbenzimidazoles have been synthesized as antimycobacterial agents. An efficient synthesis has been developed for 2-arylbenzimidazoles from o-phenylenediamines and aromatic aldehydes in molecular sieves-methanol system. The methodology is straightforward to get 2-arylbenzimidazoles (3a–3z) in excellent yields with high chemoselectivity over 2-aryl-1-benzylbenzimidazoles (4a–4z). All these benzimidazole analogues were evaluated against M. tuberculosis in BACTEC radiometric assay. The compounds 4y and 4z exhibited potential antitubercular activity against M. tuberculosis H37RV, MIC at 16?µM and 24?µM respectively. The best compound of the series i.e. compound 4y was well tolerated by Swiss-albino mice in acute oral toxicity. Compound 4y possessing a diarylbenzimidazole core, can further be optimized for better activity.

English abstract

Arylbenzimidazoles have been synthesized as antimycobacterial agents. An efficient synthesis has been developed for 2-arylbenzimidazoles from o-phenylenediamines and aromatic aldehydes in molecular sieves-methanol system. The methodology is straightforward to get 2-arylbenzimidazoles (3a–3z) in excellent yields with high chemoselectivity over 2-aryl-1-benzylbenzimidazoles (4a–4z). All these benzimidazole analogues were evaluated against M. tuberculosis in BACTEC radiometric assay. The compounds 4y and 4z exhibited potential antitubercular activity against M. tuberculosis H37RV, MIC at 16?µM and 24?µM respectively. The best compound of the series i.e. compound 4y was well tolerated by Swiss-albino mice in acute oral toxicity. Compound 4y possessing a diarylbenzimidazole core, can further be optimized for better activity.

Keywords

Tuberculosis, Molecular Docking, DNA Gyrase

Released

15.08.2018

Publisher

Elsevier

Pages from

4551

Pages to

4559

Pages count

9

URL

BibTex


@article{BUT150284,
  author="Amit K {Chaturvedi} and Amit K {Verma} and Jay Prakash {Thakur} and Sudeep {Roy} and Shashi Bhushan {Tripathi} and Balagani Sathish {Kumar} and Sadiya {Khwaja} and Naresh Kumar {Sachan} and Ashok {Sharma} and Debabrata {Chanda} and Karuna {Shanker} and Dharmendra {Saikia} and Arvind Singh {Negi}",
  title="A novel synthesis of 2-arylbenzimidazoles in molecular sieves-MeOH system and their antitubercular activity",
  annote="Arylbenzimidazoles have been synthesized as antimycobacterial agents. An efficient synthesis has been developed for 2-arylbenzimidazoles from o-phenylenediamines and aromatic aldehydes in molecular sieves-methanol system. The methodology is straightforward to get 2-arylbenzimidazoles (3a–3z) in excellent yields with high chemoselectivity over 2-aryl-1-benzylbenzimidazoles (4a–4z). All these benzimidazole analogues were evaluated against M. tuberculosis in BACTEC radiometric assay. The compounds 4y and 4z exhibited potential antitubercular activity against M. tuberculosis H37RV, MIC at 16?µM and 24?µM respectively. The best compound of the series i.e. compound 4y was well tolerated by Swiss-albino mice in acute oral toxicity. Compound 4y possessing a diarylbenzimidazole core, can further be optimized for better activity.",
  address="Elsevier",
  chapter="150284",
  doi="10.1016/j.bmc.2018.07.049",
  howpublished="online",
  institution="Elsevier",
  number="15",
  volume="26",
  year="2018",
  month="august",
  pages="4551--4559",
  publisher="Elsevier",
  type="journal article in Web of Science"
}