One pot Click chemistry: A three component reaction for the synthesis of 2-mercaptobenzimidazole linked coumarinyl triazoles as anti-tubercular agents

Ashish Anand; Manohar V Kulkarni; Shrinivas D Joshi; Sheshagiri R Dixit

doi:10.1016/j.bmcl.2016.08.045

One pot Click chemistry: A three component reaction for the synthesis of 2-mercaptobenzimidazole linked coumarinyl triazoles as anti-tubercular agents

Bioorg Med Chem Lett. 2016 Oct 1;26(19):4709-4713. doi: 10.1016/j.bmcl.2016.08.045. Epub 2016 Aug 20.

Authors

Ashish Anand¹, Manohar V Kulkarni², Shrinivas D Joshi³, Sheshagiri R Dixit³

Affiliations

¹ Department of Studies in Chemistry, Karnatak University, Pavate Nagar, Dharwad 580003, Karnataka, India.
² Department of Studies in Chemistry, Karnatak University, Pavate Nagar, Dharwad 580003, Karnataka, India. Electronic address: manohar274@gmail.com.
³ Novel Drug Design and Discovery Laboratory, Department of Pharmaceutical Chemistry, S.E.T's College of Pharmacy, Sangolli Rayanna Nagar, Dharwad 580002, Karnataka, India.

PMID: 27595420
DOI: 10.1016/j.bmcl.2016.08.045

Abstract

2-Propargylthiobenzimidazole 1, 4-bromomethyl coumarins/1-aza-coumarins 2/3 and sodium azide have been reacted in one pot under Click chemistry conditions to give exclusively 1,4-disubstituted triazoles 5a-n. Anti-tubercular assays against M. tuberculosis (H37Rv) coupled with in silico molecular docking studies indicated that dimethyl substituents 5c and 5d showed promising activity with higher C-score values.

Keywords: 1,2,3-Triazoles; 2-Mercaptobenzimidazole; 2H-Chromen-2-one; Anti-tubercular; Molecular docking; One pot Click reaction; Surflex-Dock.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antitubercular Agents / chemistry*
Benzimidazoles / chemistry*
Click Chemistry*
Molecular Docking Simulation
Triazoles / chemistry*

Substances

Antitubercular Agents
Benzimidazoles
Triazoles
2-mercaptobenzimidazole