Synthesis, antitubercular activity and docking study of novel cyclic azole substituted diphenyl ether derivatives.

Abstract:

:The re-emergence of tuberculosis (TB) as a global health problem over the past few decades, accompanied by the rise of drug-resistant strains of Mycobacterium tuberculosis, emphasizes the need for discovery of new therapeutic drugs against this disease. The emerging serious problem both in terms of TB control and clinical management prompted us to synthesize a novel series of heterocyclic o/m/p substituted diphenyl ether derivatives and determine their activity against H37Rv strain of Mycobacterium. All 10 compounds inhibited the growth of the H37Rv strain of mycobacterium at concentrations as low as 1 microg/mL. This level of activity was found comparable to the reference drugs rifampicin and isoniazid at the same concentration. Molecular modeling of the binding of the diphenyl ether derivatives on enoyl-ACP reductase, the molecular target site of triclosan, indicated that these compounds fit within the binding domain occupied by triclosan. Hence the diphenyl ether derivatives tested in this study were docked to ENR and the binding of the diphenyl ether derivatives was also estimated using a variety of scoring functions that have been compiled into the single consensus score. As the scores ranged from 47.27% to 65.81%, these bioactive compounds appear to have a novel mechanism of action against M. tuberculosis, and their structural features should be studied further for their potential use as new antitubercular drugs.

journal_name

Eur J Med Chem

authors

Kini SG,Bhat AR,Bryant B,Williamson JS,Dayan FE

doi

10.1016/j.ejmech.2008.04.013

subject

Has Abstract

pub_date

2009-02-01 00:00:00

pages

492-500

issue

2

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(08)00203-1

journal_volume

44

pub_type

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