Design, synthesis, and biological evaluation of m-amidophenol derivatives as a new class of antitubercular agents

MedChemComm
2018.0

Abstract

A series of <i>m</i>-amidophenol derivatives (<b>6a-6l</b>, <b>7a-7q</b>, <b>9a</b>, <b>9b</b>, <b>12a-12c</b>, <b>14</b> and <b>15</b>) were designed and synthesized. Their antitubercular activities were evaluated <i>in vitro</i> against <i>M. tuberculosis</i> strains H37Ra and H37Rv and clinically isolated multidrug-resistant <i>M. tuberculosis</i> strains. Ten compounds displayed minimal inhibitory concentrations (MICs) against <i>M. tuberculosis</i> H37Ra below 2.5 μg mL<sup>-1</sup> and <b>6g</b> was the most active compound (MIC = 0.625 μg mL<sup>-1</sup>). Compounds <b>6g</b> and <b>7a</b> also showed potent inhibitory activity against <i>M. tuberculosis</i> H37Rv (MIC = 0.39 μg mL<sup>-1</sup>) and several clinically isolated multidrug-resistant <i>M. tuberculosis</i> strains (MIC = 0.39-3.125 μg mL<sup>-1</sup>). The compounds did not show inhibitory activity against normal Gram-positive and Gram-negative bacteria. They exhibited low cytotoxicity against HepG2 and RAW264.7 cell lines. The results demonstrated <i>m</i>-amidophenol as an attractive scaffold for the development of new antitubercular agents.

Knowledge Graph

Similar Paper

Design, synthesis, and biological evaluation of m-amidophenol derivatives as a new class of antitubercular agents
MedChemComm 2018.0
Novel amide and sulphonamide derivatives of 6-(piperazin-1-yl)phenanthridine as potent Mycobacterium tuberculosis H37Rv inhibitors
European Journal of Medicinal Chemistry 2015.0
Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents
Bioorganic &amp; Medicinal Chemistry Letters 2019.0
Design, synthesis, andin vitrobiological evaluation of novel benzimidazole tethered allylidenehydrazinylmethylthiazole derivatives as potent inhibitors ofMycobacterium tuberculosis
MedChemComm 2018.0
Design, Synthesis, and Biological Evaluation of Pyrazolo[1,5-a]pyridine-3-carboxamides as Novel Antitubercular Agents
ACS Medicinal Chemistry Letters 2015.0
Synthesis, spectral studies and biological evaluation of a novel series of 2-substituted-5,6-diarylsubstituted imidazo(2,1-b)-1,3,4-thiadiazole derivatives as possible anti-tubercular agents
Medicinal Chemistry Research 2012.0
Design, synthesis and evaluation of novel molecules with a diphenyl ether nucleus as potential antitubercular agents
Bioorganic &amp; Medicinal Chemistry Letters 2012.0
Synthesis and evaluation of anti-tubercular activity of 6-(4-substitutedpiperazin-1-yl) phenanthridine analogues
European Journal of Medicinal Chemistry 2014.0
Studies on substituted benzo[h]quinazolines, benzo[g]indazoles, pyrazoles, 2,6-diarylpyridines as anti-tubercular agents
Bioorganic &amp; Medicinal Chemistry Letters 2013.0
Synthesis and biological evaluation of N-(aryl)-2-thiophen-2-ylacetamides series as a new class of antitubercular agents
Bioorganic &amp; Medicinal Chemistry Letters 2007.0