Synthesis of the molecular hybrid inspired by Largazole and Psammaplin A |
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Authors: | Xiaoling Yu Bingbing Zhang Guangsheng Shan Yue Wu Feng-Ling Yang Xinsheng Lei |
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Institution: | 1. School of Pharmacy, Fudan University, 826 Zhangheng Road, Pudong Zone, Shanghai 201203, China;2. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan Province 450001, China |
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Abstract: | One important class of HDAC (histone deacetylation enzymes) inhibitors is the sulfur-containing marine natural products with structural diversity. Inspired by two structurally distinguishing examples, Largazole and Psammaplin A, which possess macrocyclic depsipeptide and simple linear amide scaffold respectively, we designed one novel molecular hybrid by replacing the alkene moiety in Largazole with a semirigid amide bond. This hybrid compound has been synthesized from l-malic acid in 10 steps with an overall yield of 7%. The preliminary biological assays suggest that the replacement of trans olefin moiety with amide bond will lead to an unbeneficial effect on the inhibition against HDACs. |
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Keywords: | Marine natural product Largazole Psammaplin A Hybrid HDAC inhibitors |
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