Synthesis, 3D-QSAR analysis and biological evaluation of quinoxaline 1,4-di-N-oxide derivatives as antituberculosis agents

Bioorganic & Medicinal Chemistry Letters
2016.0

Abstract

A series of quinoxaline 1,4-di-N-oxide derivatives variously substituted at C-2 position were synthesized and evaluated for in vitro antimycobacterial activity. Seventeen compounds exhibited potential activity (MIC ⩽6.25μg/mL) against Mycobacterium tuberculosis (H37Rv), in particular the compounds 3d and 3j having an MIC value of 0.39μg/mL. None of the compounds exhibited cytotoxicity when using an MTT assay in VERO cells. To further investigate the structure-activity relationship, CoMFA (q(2)=0.507, r(2)=0.923) and CoMSIA (q(2)=0.665, r(2)=0.977) models were performed on the basis of antimycobacterial activity data. The 3D-QSAR study of these compounds can provide useful information for further rational design of novel quinoxaline 1,4-di-N-oxides for treatment of tuberculosis.

Knowledge Graph

Similar Paper

Synthesis, 3D-QSAR analysis and biological evaluation of quinoxaline 1,4-di-N-oxide derivatives as antituberculosis agents
Bioorganic & Medicinal Chemistry Letters 2016.0
Synthesis, biological evaluation and 3D QSAR study of 2,4-disubstituted quinolines as anti-tuberculosis agents
European Journal of Medicinal Chemistry 2015.0
Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives
European Journal of Medicinal Chemistry 2010.0
Design, synthesis and 3D-QSAR studies of new diphenylamine containing 1,2,4-triazoles as potential antitubercular agents
European Journal of Medicinal Chemistry 2014.0
Synthesis, biological evaluation and 3D-QSAR study of hydrazide, semicarbazide and thiosemicarbazide derivatives of 4-(adamantan-1-yl)quinoline as anti-tuberculosis agents
European Journal of Medicinal Chemistry 2014.0
Synthesis of New Quinoxaline-2-carboxylate 1,4-Dioxide Derivatives as Anti-Mycobacterium tuberculosis Agents
Journal of Medicinal Chemistry 2005.0
Synthesis, evaluation and CoMFA/CoMSIA study of nitrofuranyl methyl N-heterocycles as novel antitubercular agents
Bioorganic & Medicinal Chemistry 2018.0
Selective activity against Mycobacterium tuberculosis of new quinoxaline 1,4-di-N-oxides
Bioorganic & Medicinal Chemistry 2009.0
Design and synthesis of novel quinoxaline derivatives as potential candidates for treatment of multidrug-resistant and latent tuberculosis
Bioorganic & Medicinal Chemistry Letters 2016.0
Synthesis, anti-tuberculosis activity and 3D-QSAR study of amino acid conjugates of 4-(adamantan-1-yl) group containing quinolines
European Journal of Medicinal Chemistry 2009.0