Total synthesis and biological activity of marine alkaloid Eudistomins Y1-Y7 and their analogues.
Mar Drugs
; 11(5): 1427-39, 2013 Apr 29.
Article
in En
| MEDLINE
| ID: mdl-23629726
ABSTRACT
Eudistomin Y class compounds are a series of ß-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 ß-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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Breast Neoplasms
/
Carbolines
/
Antineoplastic Agents
Limits:
Female
/
Humans
Language:
En
Journal:
Mar Drugs
Journal subject:
BIOLOGIA
/
FARMACOLOGIA
Year:
2013
Document type:
Article
Affiliation country:
China