Synthesis and antimicrobial activities of novel 8-(1-alkyl/alkylsulphonyl/alkoxycarbonyl-benzimidazol-2-ylmethoxy)-5-chloroquinolines

Abstract

The synthesis of a series of novel 8-(1-alkyl/alkylsulphonyl/alkoxycarbonyl-benzimidazol-2-ylmethoxy)-5-chloroquinoline derivatives is reported. These derivatives were prepared by the condensation of o-phenylenediamine with [(5-chloroquinolin-8-yl)oxy]acetic acid, followed by substitution at nitrogen with different electrophilic reagents in presence of an appropriate base to give a series of nitrogen heterocycles containing the benzimidazole and quinoline nuclei. The structures of the compounds were confirmed based on 1H-NMR, 13C-NMR, IR and mass spectral data. Almost all the compounds exhibited promising antibacterial activity against Salmonella typhimurium and Staphylococcus aureus. Some of the compounds showed good antifungal activities against Aspergillus niger but the antifungal activities against Candida albicans were disappointing.

Keywords

• heterocyclic
• benzimidazole
• quinoline
• antibacterial
• antifungal.