Glycosyl derivatives of 2-bromosugar of selected non-steroidal anti-inflammatory drugs. Synthesis and QSAR data

Abstract

On the basis of molecular modeling and calculation of physicochemical SAR data we obtained new derivatives of 2-bromosugars 5a– d and 6 for widely used non-steroidal anti-inflammatory drugs (NSAIDs). Compounds 5a– d and 6 were synthesized as stable, crystalline compounds from the reaction of phosphoroates 1– 3 with salicylic acid ( 4a), aspirin ( 4b), diclofenac ( 4c) and indomethacin ( 4d) in an aprotic solvent. The reaction took place in the presence of silver carbonate as the activator of leaving groups with high stereoselectivity and good yields. The structures of the new derivatives of 5a– d and 6 for NSAIDs were established by spectroscopic methods 1H and 13C NMR, and elemental analyses.