Camphorsulfonic acid catalysed facile tandem double Friedlander annulation protocol for the synthesis of phenoxy linked bisquinoline derivatives and discovery of antitubercular agents

Bioorganic & Medicinal Chemistry Letters
2012.0

Abstract

A series of phenoxy linked bisquinoline derivatives were synthesised from the Friedlander annulation of 2-(4-acetylphenoxy)-1-aryl-1-ethanones with 2-aminobenzophenone in good yields using (±)-camphor-10-sulfonic acid (CSA) as the catalyst. These compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and among the 23 compounds screened, 2-(3-bromophenyl)-6-chloro-3-[4-(6-chloro-4-phenyl-2-quinolyl)phenoxy]-4-phenylquinoline (3q) and 2-(4-bromophenyl)-6-chloro-3-[4-(6-chloro-4-phenyl-2-quinolyl)phenoxy]-4-phenylquinoline (3o) were found to be the most active compounds with MIC of 1.1 and 2.2 μM against MTB. The cytotoxic effects against mouse fibroblasts (NIH 3T3) in vitro were evaluated for 3o and 3q, which displayed no toxic effects against mouse fibroblast cell line NIH 3T3.

Knowledge Graph

Similar Paper

Camphorsulfonic acid catalysed facile tandem double Friedlander annulation protocol for the synthesis of phenoxy linked bisquinoline derivatives and discovery of antitubercular agents
Bioorganic & Medicinal Chemistry Letters 2012.0
Synthesis of 3-heteroarylthioquinoline derivatives and their in vitro antituberculosis and cytotoxicity studies
European Journal of Medicinal Chemistry 2011.0
Design, development of new synthetic methodology, and biological evaluation of substituted quinolines as new anti-tubercular leads
Bioorganic & Medicinal Chemistry Letters 2016.0
Three-component, one-pot synthesis of anthranilamide Schiff bases bearing 4-aminoquinoline moiety as Mycobacterium tuberculosis gyrase inhibitors
Bioorganic & Medicinal Chemistry Letters 2017.0
Synthesis, antimicrobial, and cytotoxicity studies of novel sulfur-linked quinoline–coumarin bisheterocycles
Medicinal Chemistry Research 2014.0
Identification of benzofuro[2,3- b ]quinoline derivatives as a new class of antituberculosis agents
European Journal of Medicinal Chemistry 2010.0
Synthesis and biological evaluation of dihydroquinoline carboxamide derivatives as anti-tubercular agents
European Journal of Medicinal Chemistry 2018.0
Synthesis, 3D-QSAR analysis and biological evaluation of quinoxaline 1,4-di-N-oxide derivatives as antituberculosis agents
Bioorganic & Medicinal Chemistry Letters 2016.0
New 1,3-oxazolo[4,5-c]quinoline derivatives: Synthesis and evaluation of antibacterial and antituberculosis properties
European Journal of Medicinal Chemistry 2010.0
Design and synthesis of some new quinoline-3-carbohydrazone derivatives as potential antimycobacterial agents
Bioorganic & Medicinal Chemistry Letters 2010.0