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Design, synthesis and cytotoxicity of bengamide analogues and their epimers.

ABSTRACT: Starting from d-glycero-d-gulo-heptonic acid ?-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.

SUBMITTER: Phi TD

PROVIDER: S-EPMC6072509 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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Design, synthesis and cytotoxicity of bengamide analogues and their epimers.

Phi Thi Dao TD Doan Thi Mai Huong H Tran Van Hieu VH Truong Bich Ngan BN Tran Tuan Anh TA Vu Van Loi VL Chau Van Minh VM Pham Van Cuong VC

MedChemComm 20161221 2

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 ...[more]

PMID: 30108762

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