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

Abstract : A series of 16 new ethyl [Formula: see text]-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.
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Submitted on : Tuesday, October 23, 2018 - 4:28:13 PM
Last modification on : Friday, October 16, 2020 - 3:31:42 AM
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Christelle N'Ta Ambeu, Rémy Le Guével, Anne Corlu, Janat Akhanovna Mamyrbekova, Jean-Pierre Bazureau. A practical multi-step synthesis of ethyl N-functionalized β-amino benzimidazole acrylate derivatives as promising cytotoxic agents. Molecular Diversity, Springer Verlag, 2018, 22 (3), pp.685-708. ⟨10.1007/s11030-018-9824-5⟩. ⟨hal-01808102⟩

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