A new approach for the N- and S-galactosylation of 5-arylidene-2-thioxo-4-thiazolidinones.

Abstract

N- and S-galactosylation was carried out via the reaction of 5-((Z)-arylidene)-2-thioxo-4-thiazolidinones with 2,3,4,6-tetra-O-acetyl-α-d-galactopyranosyl bromide under alkaline conditions or under silylation conditions. Deacetylation of the N-galactosylation products was performed with concentrated hydrochloric acid in methanol (3.5%) or sodium methoxide in methanol without cleavage of the 2-thioxo-4-thaizolidinone ring by means of acid hydrolysis. The anomers were separated by flash column chromatography, and their configurations were assigned by NMR spectroscopy. The deprotected nucleosides were screened against leukemia L-1210 and were found inactive.

• Authors: Ahmed I Khodair, Jean-Pierre Gesson
• Journal: Carbohydrate research (Carbohydr Res) Vol. 346 Issue 18 Pg. 2831-7 (Dec 27 2011) ISSN: 1873-426X [Electronic] Netherlands
• PMID: 22088884 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2011 Elsevier Ltd. All rights reserved.

Chemical References

• Thiazolidinediones
• Galactose

Topics

• Galactose (chemistry)
• Molecular Structure
• Stereoisomerism
• Thiazolidinediones (chemical synthesis, chemistry)