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- W2085757712 abstract "Previous structure−activity relationship studies of adenophostin A, a potent IP3 receptor agonist, led us to design the novel adenophostin A analogues 5a−c, conjugating an aromatic group at the 5‘-position to develop useful IP3 receptor ligands. The common key intermediate, a d-ribosyl α-d-glucoside 10α, was stereoselectively synthesized by a glycosidation with the 1-sulfinylglucoside donor 11, which was conformationally restricted by a 3,4-O-cyclic diketal protecting group. After introduction of an aromatic group at the 5-position of the ribose moiety, an adenine base was stereoselectively introduced at the anomeric β-position to form 7a−c, where the tetra-O-i-butyryl donors 9a−c were significantly more effective than the corresponding O-acetyl donor. Thus, the target compounds 5a−c were synthesized via phosphorylation of the 2‘, 3‘ ‘, and 4‘ ‘-hydroxyls. The potencies of compounds 5a−c for Ca2+ release were shown to be indistinguishable from that of adenophostin A, indicating that bulky substitutions at the 5‘-position of adenophostin A are well-tolerated in the receptor binding. This biological activity of 5a−c can be rationalized by molecular modeling using the ligand binding domain of the IP3 receptor." @default.
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- W2085757712 date "2006-08-19" @default.
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- W2085757712 title "Synthesis of Adenophostin A Analogues Conjugating an Aromatic Group at the 5‘-Position as Potent IP<sub>3</sub> Receptor Ligands" @default.
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- W2085757712 doi "https://doi.org/10.1021/jm060310d" @default.
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