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Analogues of the Ca 2+ -releasing intracellular messenger d- myo -inositol 1,4,5-trisphosphate [ 1 , Ins(1,4,5)P 3 ] are important synthetic targets. Replacement of the α-glucopyranosyl motif in the natural product mimic adenophostin 2 by d- chiro -inositol in d- chiro -inositol adenophostin 4 increased the potency. Similar modification of the non-nucleotide Ins(1,4,5)P 3 mimic ribophostin 6 may increase the activity. d- chiro -Inositol ribophostin 10 was synthesized by coupling as building blocks suitably protected ribose 12 with l-(+)-3- O -trifluoromethylsulfonyl-6- O - p -methoxybenzyl-1,2:4,5-di- O -isopropylidene- myo -inositol 11 . Separable diastereoisomeric 3- O -camphanate esters of (±)-6- O - p -methoxy-benzyl-1,2:4,5-di- O -isopropylidene- myo -inositol allowed the preparation of 11 . Selective trans -isopropylidene deprotection in coupled 13 , then monobenzylation gave separable regioisomers 15 and 16 . p -Methoxybenzyl group deprotection of 16 , phosphitylation/oxidation, then deprotection afforded 10 , which was a full agonist in Ca 2+ -release assays; its potency and binding affinity for Ins(1,4,5)P 3 R were similar to those of adenophostin. Both 4 and 10 elicited a store-operated Ca 2+ current I CRAC in patch-clamped cells, unlike Ins(1,4,5)P 3 consistent with resistance to metabolism. d- chiro -Inositol ribophostin is the most potent small-molecule Ins(1,4,5)P 3 receptor agonist without a nucleobase yet synthesized.

journal of medicinal chemistry

<scp>d</scp>-<i>chiro</i>-Inositol Ribophostin: A Highly Potent Agonist of <scp>d</scp>-<i>myo</i>-Inositol 1,4,5-Trisphosphate Receptors: Synthesis and Biological Activities

d-chiro-Inositol Ribophostin: A Highly Potent Agonist of d-myo-Inositol 1,4,5-Trisphosphate Receptors: Synthesis and Biological Activities