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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 (2012-01-27)
Nidhin Paul, Muthuchamy Murugavel, Shanmugam Muthusubramanian, Dharmarajan Sriram
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.

MATERIALS
Product Number
Brand
Product Description

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Rifampicin, ≥97% (HPLC), powder
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(1S)-(+)-10-Camphorsulfonic acid, 99%
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Isoniazid, analytical standard, ≥99% (TLC)
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Camphor-10-sulfonic acid (β), 98%
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(+)-Camphor-10-sulfonic acid, purum, ≥98.0% (T)
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(−)-Camphor-10-sulfonic acid, purum, ≥98.0% (T)