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Molecular Diversity

, Volume 22, Issue 3, pp 685–708 | Cite as

A practical multi-step synthesis of ethyl N-functionalized \(\varvec{\upbeta }\)-amino benzimidazole acrylate derivatives as promising cytotoxic agents

  • Christelle N’Ta Ambeu
  • Rémy Le Guével
  • Anne Corlu
  • Janat Akhanovna Mamyrbekova
  • Jean-Pierre Bazureau
Original Article

Abstract

A series of 16 new ethyl \(\upbeta \)-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.

Keywords

Benzimidazole Reductive amination Transamination Microwave Cytotoxicity 

Notes

Acknowledgements

One of us (C.N.A.) wishes to thank the "Elec-BTP" and the "Ministère de l’Enseignement Supérieur et de la Recherche Scientifique de Côte d’Ivoire" for grants. Financial support of this program carried out under the French National Cancer Institute “Cancéropôle Grand Ouest” by “Valorisation des produits de la mer en cancérologie” contract, is gratefully acknowledged. The authors are grateful to the assistance of the staff of the CRMPO analytical chemistry core facility for HRMS analysis (CRMPO platform, ScanMAT UMS 2001 CNRS, Université de Rennes 1, Bât. 11A, Campus de Beaulieu, Rennes, France).

Compliance with ethical standards

Conflicts of interest

The authors declare no conflict of interest.

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Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Institut des Sciences Chimiques de Rennes (ISCR), UMR CNRS 6226, groupe COrIntUniversité de Rennes 1 (UR1)Rennes CedexFrance
  2. 2.Laboratoire de Chimie Bio Organique et Substances Naturelles (LCBOSN)Université Nangui Abrogoua (UNA)AbidjanCôte d’Ivoire
  3. 3.Université de Rennes 1Rennes CedexFrance
  4. 4.Université de Rennes 1Rennes CedexFrance
  5. 5.S2Wave platform, ScanMAT UMS 2001 CNRSUniversité de Rennes 1 (UR1)Rennes CedexFrance

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