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Total Synthesis and Biological Activity of Marine Alkaloid Eudistomins Y1–Y7 and Their Analogues
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
Departments of Medicine, Oncology, and Pharmacology and Therapeutics, Lady Davis Institute for Medical Research, Segal Cancer Center of the Sir Mortimer B. Davis Jewish General Hospital, McGill University, Montreal, QC H3T 1E2, Canada
These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 25 February 2013; in revised form: 25 March 2013 / Accepted: 7 April 2013 / Published: 29 April 2013
Abstract: 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.
Keywords: marine alkaloid; Eudistomins Y1–Y7; β-carboline; Pictet-Spengler reaction
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Jin, H.; Zhang, P.; Bijian, K.; Ren, S.; Wan, S.; Alaoui-Jamali, M.A.; Jiang, T. Total Synthesis and Biological Activity of Marine Alkaloid Eudistomins Y1–Y7 and Their Analogues. Mar. Drugs 2013, 11, 1427-1439.
Jin H, Zhang P, Bijian K, Ren S, Wan S, Alaoui-Jamali MA, Jiang T. Total Synthesis and Biological Activity of Marine Alkaloid Eudistomins Y1–Y7 and Their Analogues. Marine Drugs. 2013; 11(5):1427-1439.
Jin, Huijuan; Zhang, Puyong; Bijian, Krikor; Ren, Sumei; Wan, Shengbiao; Alaoui-Jamali, Moulay A.; Jiang, Tao. 2013. "Total Synthesis and Biological Activity of Marine Alkaloid Eudistomins Y1–Y7 and Their Analogues." Mar. Drugs 11, no. 5: 1427-1439.