Acta Pharm. 59 (2009) 55-71

full paper

Original research paper

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

ESLAM REDA EL-SAWY, FATMA A. BASSYOUNI, SHERIFA H. ABU-BAKR, HANAA M. RADY and MOHAMED M. ABDLLA

eslamelsawy@gmail.com

¹Chemistry Department of Natural Compounds, National Research Centre, Cairo, Egypt

²Chemistry Department of Natural and Microbial Products, National Research Centre, Cairo, Egypt

³Univeterinary Research Unit, Pharmaceutical Company, Cairo, Egypt

Accepted January 5, 2010

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)imidazole (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 mg mm^-2 showed that 3-(1-substituted indol-3-yl)quinoxalin-2(1H)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 ± 0.3 %.

Keywords: 2-chloro-3-(1-benzyl)quinoxalines, 2-chloro-3-(1-benzoylindol-3-yl)quinoxalines, antimicrobial, ovarian anti-cancer