Synthesis of analogues of myo-inositol 1,4,5-trisphosphate that contain sulfonamide, sulfate, methylphosphonate, and carboxymethyl groups.
The syntheses are described of four isosteric racemic myo-inositol 1,4,5-trisphosphate (1) analogues with the phosphate groups replaced by sulfonamide (2), sulfate (3), methylphosphonate (4), and carboxymethyl (5). None of these compounds had any affinity for the IP3 receptor or induced platelet aggregation.
Westerduin
P
P
Akzo Pharma, Organon Scientific Development Group, Oss, Netherlands.
Willems
H A
HA
van Boeckel
C A
CA
D015220:Calcium Channels; D006801:Humans; D015544:Inositol 1,4,5-Trisphosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D053496:Inositol 1,4,5-Trisphosphate Receptors; D008745:Methylation; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D010974:Platelet Aggregation / Q000187:drug effects; D011956:Receptors, Cell Surface / Q000378:metabolism; D018160:Receptors, Cytoplasmic and Nuclear; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D013464:Sulfuric Acids / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology
D015220:Calcium Channels; C506926:ITPR1 protein, human; D053496:Inositol 1,4,5-Trisphosphate Receptors; D063065:Organophosphonates; D011956:Receptors, Cell Surface; D018160:Receptors, Cytoplasmic and Nuclear; D013449:Sulfonamides; D013464:Sulfuric Acids; D015544:Inositol 1,4,5-Trisphosphate