Carbohydrate Research 2011-01-01

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

Ahmed I. Khodair, Jean-Pierre Gesson, Ahmed I. Khodair, Jean-Pierre Gesson

Index: Carbohydr. Res. 346 , 2831-2837, (2011)

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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.Copyright © 2011 Elsevier Ltd. All rights reserved.