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
Advanced Center for Bioorganic Chemistry , Institute of Marine Biochemistry , VAST , 18 Hoang Quoc Viet , Caugiay , Hanoi , Vietnam . Email:
Graduate University of Science and Technology , VAST , 18 Hoang Quoc Viet , Caugiay , Hanoi , Vietnam.
Medchemcomm. 2016 Dec 21;8(2):445-451. doi: 10.1039/c6md00587j. eCollection 2017 Feb 1.
Starting from d--d--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 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 (2') and (2'). 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.
从d--d--庚糖酸γ-内酯和氨基酸出发，合成了一系列非对映异构的苯甲酰胺类似物。反应条件的优化表明，微波辐射辅助是制备氨基内酰胺以及内酯与氨基内酰胺偶联反应的有效方法。对六种癌细胞系（KB、HepG2、LU1、MCF7、HL60和Hela）的细胞毒性活性评估表明，C-2'的构型似乎对化合物(2')和(2')的细胞毒性活性至关重要。此外，受保护的丙酮化物化合物与其相应的脱保护苯甲酰胺类似物的细胞毒性比较表明，酮化物侧链的灵活性是其细胞毒性活性所必需的。
