Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivatives

Abstract

Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivatives

Starting from 1-benzyl- (2a) and 1-benzoyl-3-bromoacetyl indoles (2b) new heterocyclic, 2-thioxoimidazolidine (4a, b), imidazolidine-2,4-dione (5a, b), pyrano(2,3-[d])imida-zole (8a, b and 9a, b), 2-substituted quinoxaline (11a, b-17a, b) and triazolo(4,3-[a])quinoxaline derivatives (18a, b and 19a, b) were synthesized and evaluated for their antimicrobial and anticancer activities. Antimicrobial activity screening performed with concentrations of 0.88, 0.44 and 0.22 μg mm[-2] showed that 3-(1-substituted indol-3-yl)quinoxalin-2(1[H])ones (11a, b) and 2-(4-methyl piperazin-1-yl)-3-(1-substituted indol-3-yl) quinoxalines (15a, b) were the most active of all the tested compounds towards [P. aeruginosa, B. cereus] and [S. aureus] compared to the reference drugs cefotaxime and piperacillin, while 2-chloro-3-(1-substituted indol-3-yl)quinoxalines (12a, b) were the most active against C. [albicans] compared to the reference drug nystatin. On the other hand, 2-chloro-3-(1-benzyl indol-3-yl) quinoxaline 12a display potent efficacy against ovarian cancer xenografts in nude mice with tumor growth suppression of 100.0 ± 0.3 %.