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Synthesis and Antiproliferative Activity in vitro of New 2-Aminobenzimidazole Derivatives. Part 3 [1]. Reactions of 2-Arylideneaminobenzimidazole with Selected 1,3-Diketones

Nawrocka W., Sztuba B., Dryś A., Wietrzyk J., Kosendiak J., Opolski A.

Polish Journal of Chemistry

2006

Vol. 80, nr 2

279-287

A series of pyrimido[1,2-a]benzimidazole derivatives has been synthesized in the reactions of 2-aminobenzimidazole Schiff bases 1-6 with selected _-diketones; acetylacetone 7-12 or benzoylacetone 13-18. The structures 4, 7-18 were confirmed by the results of elemental analysis and their IR, 1H NMR and MS spectra. Compounds 4, 7-18 were examined for their antiproliferative activityin vitro against 3 cancer cell lines: P338 (mice leukemia), A549 (non-small cell lung carcinoma), SW707 (rectal adenocarcinoma), using SRB (sulphorhodamine B) or MTT (3-(4,5-dimethylthiazol- 2-yl)-2,5-diphenyl tetrazolium bromide) technique. The Schiff base 4 and tricyclic derivatives 9, 14, 16 exhibited the highest cytotoxic activity in vitro.

Synthesis and Antiproliferative Activity in vitro of New 2-Aminobenzimidazole Derivatives. Part 2 [1]

Nawrocka W., Sztuba B., Liszkiewicz H., Kowalska M., Wietrzyk J., Nevozhai D., Opolski A.

Polish Journal of Chemistry

2005

Vol. 79 / nr 4

709-716

A series of 2-methylpyrimido[1,2-a]benzimidazole derivatives has been synthesized in the reactions of 2-aminobenzimidazole (1) with selected halogeno _-diketones: 1,1,1- trifluoro- 2, 1-chloro-1,1-difluoro- 3, 3-chloro-2,4-pentadione- 4 and with 4-fluorobenzoylacetone 5. 2-Aminobenzimidazole (1) in the reactions with _-chloro- and _- bromocinnamaldehyde gave Schiff bases 10 and 11 which have been subjected to reduction using NaBH4 and 3-benzylideno-1,2-dihydro- (12) and 3-benzylideno-1,2,9,10- tetrahydroimidazo[1,2-a]benzimidazole (13) were obtained. The structures 2-13 were identified by the results of elemental analysis and their IR, 1H NMR and MS spectra. Compounds 2-13 were examined for their antiproliferative activity in vitro against the cells of 3 human cancer cell lines, using SRB (sulphorhodamine B) or MTT (3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) technique. Four out of all tested compounds revealed cytotoxic activity in vitro.