Synthesis of 5-phosphonate analogues of myo-inositol 1,4,5-trisphosphate: Possible intracellular calcium antagonists

Article abstract of DOI:10.1016/S0040-4039(00)79454-8

The racemic 5-phosphonate analogues IV and V of myo-inositol 1,4,5-trisphosphate were readily accessible by bisphosphorylation of the common precursor 6, removal of the p-methoxybenzyl group, phosphonylation and subsequent hydrogenolysis of the benzyl protecting groups. The methylphosphonate analogue IV acted as a calcium antagonist in permeabilized human platelets, whereas the (difluoromethyl)phosphonate V exhibited only very little antagonistic activity.