Synthesis of glycose carbamides and evaluation of the induction of erythroid differentiation of human erythroleukemic K562 cells

A series of carbamides derived from 1,2:5,6-di-O-isopropylidene-d-gluco- (1) and d-allofuranose (3) as well as their 5,6-O-deprotected analogues (2 and 4) and methyl 3,4-O-isopropylidene-α- and β-d-galactopyranosides (5 and 6) have been prepared in order to evaluate their ability to induce erythroid differentiation of human erythroleukemic K562 cells. Twenty out of 51 carbamides tested exhibit an appreciable activity as inducers of erythroid differentiation and have been fully characterized and described.

Graphical abstractA series carbamides derived from six aminosugars have been synthesized and tested as inducers for the erythroid differentiation of human K562 cells. Twenty new carbamides are active alone or in synergism with sub-optimal concentration of ara-C. All active compounds have been characterized by detailed NMR analysis.Figure optionsDownload full-size imageDownload as PowerPoint slide