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.
Total Synthesis and Bioactivity of the Marine Alkaloid Pityriacitrin and Some of Its Derivatives. -A novel access to pityriacitrin (IIIa) and several of its analogues via modified Pictet-Spengler reaction is described. Biological studies reveal that (IIIa) has a weak antiproliferative activity against a panel of breast and prostate cancer cell lines, whereas some of the derivatives exhibit stronger activity, which is associated with induction of both cell apoptosis and necrosis. -(ZHANG, P.; SUN, X.; XU, B.; BIJIAN, K.; WAN, S.; LI, G.; ALAOUI-JAMALI, M.; JIANG*, T.; Eur. J. Med. Chem. 46 (2011) 12, 6089-6097, http://dx.
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