title: Total synthesis and biological activity of marine alkaloid Eudistomins Y1-Y7 and their analogues.
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.
authors: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. jiangtao@ouc.edu.cn
authors: Huijuan
authors: H
authors: Jin
authors: Puyong
authors: P
authors: Zhang
authors: Krikor
authors: K
authors: Bijian
authors: Sumei
authors: S
authors: Ren
authors: Shengbiao
authors: S
authors: Wan
authors: Moulay A
authors: MA
authors: Alaoui-Jamali
authors: Tao
authors: T
authors: Jiang
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000188:drug therapy* / Q000473:pathology; D002243:Carbolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D005260:Female; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
chemical_list: D000970:Antineoplastic Agents; D002243:Carbolines
references: Bioorg Med Chem Lett. 2012 Mar 15;22(6):2296-9
references: 22342628
references: Org Lett. 2010 Sep 17;12(18):4086-9
references: 20715768
references: Bioorg Med Chem. 2012 Jul 1;20(13):4082-7
references: 22652254
references: Asian Pac J Trop Biomed. 2012 Aug;2(8):660-4
references: 23569990
references: Eur J Med Chem. 2011 Dec;46(12):6089-97
references: 22047643
references: J Nat Prod. 2008 Feb;71(2):163-6
references: 18247569
references: J Am Chem Soc. 2002 Nov 6;124(44):13179-84
references: 12405846
references: J Med Chem. 1998 Sep 24;41(20):3831-44
references: 9748358