Design, synthesis and cytotoxicity of bengamide analogues and their epimers12. Issue 2 (17th January 2017)

• Record Type: Journal Article
• Authors: Phi, Thi Dao; Doan Thi Mai, Huong; Tran, Van Hieu; Truong, Bich Ngan; Tran, Tuan Anh; Vu, Van Loi; Chau, Van Minh; Pham, Van Cuong
• Is Part Of: MedChemComm. Volume 8:Issue 2(2017)
• Page Start: 445
• Page End: 451
• Publication Date: 2017-01-17
• Subjects: Pharmaceutical chemistry -- Periodicals; 615.19
• DOI: 10.1039/c6md00587j
• Languages: English
• ISSNs: 2040-2503

Abstract

Abstract : The C-2′ of the lactam rings and the flexibility of polyketide chain should be critical for the cytotoxicity of bengamides. Abstract : Starting fromd - 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 lactone5 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 compounds8b (2′ R ) and8a (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.