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Regioselective Synthesis of Novel 3‐Thiazolidine Acetic Acid Derivatives from Glycosido Ureides
Author(s) -
Li Yuxin,
Chen Wei,
Yang Xiaoping,
Yu Guanping,
Mao Mingzhen,
Zhou Yunyun,
Liu Tuanwei,
Li Zhengming
Publication year - 2011
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2011.01241.x
Subject(s) - thiazolidine , chemistry , acetic acid , thiourea , moiety , regioselectivity , ethyl acetate , ethyl acetoacetate , stereochemistry , medicinal chemistry , steric effects , organic chemistry , catalysis
A series of 3‐thiazolidine acetic acid‐2‐(per‐ O ‐acetylglycosyl)‐1′‐imino‐α‐(substituted)‐4‐oxo ethyl ester derivatives ( 3a–t ) were prepared via the reaction of substituted amino acid‐ N ‐[(per‐ O ‐acetylglycosylamino)thioxomethyl]‐ethyl ester with ethyl bromoacetate. The crystal structure of 3‐thiazolidine acetic acid‐2‐(2′,3′,4′,6′‐tetra‐ O ‐acetyl‐β‐ d ‐galactoyranosyl)‐1′‐imino‐α‐methyl‐4‐oxo ethyl ester 3g and 1 H‐ 13 C HMBC (2D NMR experiments) measurements of 3‐thiazolidine acetic acid‐2‐(2′,3′,4′,6′‐tetra‐ O ‐acetyl‐β‐ d ‐galactopyranosyl)‐1′‐imino‐α‐(1‐methylthio)ethyl‐4‐oxo ethyl ester 3j revealed the exclusive regioselectivity during the closure of these rings toward the N‐2 position of the thiourea moiety. Furthermore, the crystal structure of compound 3g showed that the attack of N‐1 was blocked by sugar ring owing to the steric effect. The bioactivity data suggested that compound 2e has mild anticancer activity.