title: 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.affiliation: Chemistry Department, Faculty Science, Kafrelsheikh University, 33516 Kafrelsheikh, Egypt. khodair_2005@yahoo.com
authors.forename: Ahmed I
authors.initials: AI
authors.lastname: Khodair
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Gesson
mesh_terms: D005690:Galactose / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D045162:Thiazolidinediones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D045162:Thiazolidinediones; D005690:Galactose