2. Academic Validation
  3. Design, synthesis and cytotoxicity of bengamide analogues and their epimers

Design, synthesis and cytotoxicity of bengamide analogues and their epimers

  • Medchemcomm. 2016 Dec 21;8(2):445-451. doi: 10.1039/c6md00587j.
Thi Dao Phi 1 2,  Huong Doan Thi Mai 1,  Van Hieu Tran 1,  Bich Ngan Truong 1,  Tuan Anh Tran 1 3,  Van Loi Vu 1,  Van Minh Chau 1,  Van Cuong Pham 1
Affiliations

Affiliations

  • 1 Advanced Center for Bioorganic Chemistry , Institute of Marine Biochemistry , VAST , 18 Hoang Quoc Viet , Caugiay , Hanoi , Vietnam . Email: phamvc@imbc.vast.vn ; ; Tel: +84437917049.
  • 2 Graduate University of Science and Technology , VAST , 18 Hoang Quoc Viet , Caugiay , Hanoi , Vietnam.
  • 3 University of Science and Technology of Hanoi , VAST , 18 Hoang Quoc Viet , Caugiay , Hanoi , Vietnam.
PMID: 30108762 DOI: 10.1039/c6md00587j
Abstract

Starting from d-glycero-d-gulo-heptonic acid γ-lactone and Amino acids, a number of diastereoisomeric bengamide analogues were synthesized. Optimization of the reaction conditions revealed that microwave irradiation assistance is a powerful method for the preparation of aminolactams, as well as for the coupling reactions of the lactone 5 with aminolactams. Cytotoxic activity evaluation against six Cancer cell lines (KB, HepG2, LU1, MCF7, HL60, and Hela) demonstrated that the configuration of C-2' seems to be critical for the cytotoxic activity of compounds 8b (2'R) and 8a (2'S). Additionally, comparison of cytotoxicity of the protected acetonide compounds with that of their corresponding deprotected bengamide analogues suggested that the flexibility of the ketide side chain should be required for their cytotoxic activity.

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