Synthesis and Antimicrobial Activity of Some Novel 7-Chloro-4-aminoquinoline Derivatives

摘要

A number of novel 7-chloro-4-aminoquinoline derivatives have been efficiently synthesized by nucleophilic aromatic substitution reaction of 4,7-dichloroquinoline with alpha,omega-diaminoalkanes of variable carbon-chain length. Treatment of the intermediates with substituted aromatic/heteroaromatic aldehydes has led to the corresponding Schiff bases. Structures of the products have been elucidated from FTIR, H-1, and C-13 NMR, and mass spectra. Antimicrobial tests of the compounds have indicated that the most active ones displayed MIC values in the range of 1.5 to 12.5 mu g/mL, however they displayed no antifungal activity. According to the accumulated data, length of the carbon-chain linker and electronic properties of the compounds are decisive for their biological activity. Molecular docking studies have supported the above relationships.