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

作者：Khodair Ahmed I^*; Gesson Jean Pierre

来源：Carbohydrate Research, 2011, 346(18): 2831-2837.

DOI：10.1016/j.carres.2011.09.035

• 2-Thioxo-4-thiazolidinone
• 2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranosyl bromide
• N-galactosylation
• S-galactosylation
• Antileukemic activity

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-alpha-D-galactopyranosyl bromide under alkaline conditions or under silylaision 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-thiazolidinone 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-120 and were found inactive.

• 出版日期2011-12-27