Synthesis and antiherpes simplex virus activity of 9-[(1, 3-dihydroxy-2-propylthio) methyl] guanine

…, DF Smee, TR Matthews, JPH Verheyden

Index: McGee; Martin; Smee; Matthews; Verheyden Journal of Medicinal Chemistry, 1985 , vol. 28, # 9 p. 1242 - 1245

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Citation Number: 19

Abstract

The synthesis of the thio analogue (thio-DHPG, 2) of 9-[(1, 3-dihydroxy-2-propoxy) methyl] guanine (DHPG, 1) is described. The synthesis of 2 proceeded via the condensation of acetoxymethyl sulfide 9 with diacetylguanine 10 to give the protected nucleoside analogue 11. Although catalytic hydrogenolysis failed, the benzyl ether functionalities of 11 were successfully cleaved by an acetolysis reaction to furnish 14. Ammonolysis of 14 gave 2, ...