A practical multi-step synthesis of ethyl N-functionalized -amino benzimidazole acrylate derivatives as promising cytotoxic agents

作者：Ambeu Christelle N'Ta; Le Guevel Remy; Corlu Anne; Mamyrbekova Janat Akhanovna; Bazureau Jean Pierre^*

来源：Molecular Diversity, 2018, 22(3): 685-708.

DOI：10.1007/s11030-018-9824-5

• Benzimidazole
• Reductive amination
• Transamination
• Microwave
• Cytotoxicity

A series of 16 new ethyl -amino benzimidazole acrylate derivatives 12(a-p) with a (2E)-s-cis/trans conformation and bearing two points of diversity was designed and synthesized by using a multi-step strategy (reductive amination, deprotection in acidic media and transamination) in moderate to good yields from ethyl 3-dimethylamino-2-(1H-benzimidazol-2-yl)acrylate (5) and monosubstituted N-Boc diamines (7a,7b) as starting building blocks. Products 12 were evaluated for their in vitro cytotoxic potential against six selected human cell lines (Huh7-D12, Caco2, MDA-MB231, HCT116, PC3 and NCI-H727). Compounds 12a, 12e and 12l exhibited selective and micromolar antitumor activities against Huh7-D12 and Caco2 cell lines.

• 出版日期2018-8