Application of 2,4-bis(halomethyl)quinoline: synthesis and biological activities of 2,4-bis(benzofuran-2-yl)- and 2,4-bis(aroxymethyl)quinolines

Abstract

In the present investigation, the synthesis of a new type of halomethylquinoline building block, i.e., ethyl 4-(bromomethyl)-2-(chloromethyl)quinoline-3-carboxylate, and its synthetic applications in the reaction with salicylaldehydes or phenols to make a range of structurally novel and intriguing 2,4-bis(benzofuran-2-yl)quinoline- and 2,4-bis(aroxymethyl)quinoline-3-carboxylic acids is described. Our newly synthesized compounds belong to a new class of quinoline derivatives, and their structures were elucidated on the basis of their spectral data and elemental analyses. Screening for in vitro anti-tubercular against Mycobacterium smegmatis and anti-bacterial activities against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa was carried out. Compounds 5e and 5g showed significant anti-tubercular activity comparable with the reference rifampicin and might be used as promising candidates for further investigation.

Keywords: Aroxymethyl; Benzofuran; Bromomethyl; Chloromethyl; Phenol; Quinoline; Salicylaldehyde.