Total synthesis and biological activity of marine alkaloid Eudistomins Y1-Y7 and their analogues.
Total synthesis and biological activity of marine alkaloid Eudistomins Y1-Y7 and their analogues.
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DOI：
10.3390/md11051427
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发表时间：
2013-04-29
期刊：
影响因子：
5.4
通讯作者：
Jiang T
中科院分区：
文献类型：
--
作者：
Jin H;Zhang P;Bijian K;Ren S;Wan S;Alaoui-Jamali MA;Jiang T
Eudistomin Y class compounds are a series of β-carbolines which was originally isolated from a marine turnicate or ascidian near the South Korea Sea. These compounds contain bromo-substituted groups, which is one of the typical characters of marine natural products. We report herein the chemical synthesis and biological evaluation of seven new β-carboline-based metabolites, Eudistomins Y1–Y7, and their hydroxyl-methylated phenyl derivatives. Using bromo-substituted tryptamines and bromo-substituted phenylglyoxals as the key intermediates, Eudistomins Y1–Y7 and their derivatives were synthesized via the acid-catalyzed Pictet-Spengler reaction and fully characterized by 1H- and 13C-NMR and mass spectroscopy. Biological studies revealed that all of the compounds showed moderate growth inhibitory activity against breast carcinoma cell line MDA-231 with IC50 of 15–63 μM and the inhibitory activities of hydroxyl-methylated phenyl products were higher than that of the corresponding natural products Eudistomins Y1–Y7.
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