Synthesis and evaluation of 2-amino-9-(3-hydroxymethyl-4-alkoxycarbonyloxybut-1-yl) purines as potential prodrugs of penciclovir

DK Kim, N Lee, YW Kim, K Chang, JS Kim…

Index: Kim, Dae-Kee; Lee, Namkyu; Kim, Young-Woo; Chang, Kieyoung; Kim, Jae-Sun; Im, Guang-Jin; Choi, Won-Son; Jung, Inho; Kim, Taek-Soo; Hwang, Yong-Youn; Min, Dong-Sun; Um, Key An; Cho, Yong-Baik; Kim, Key H. Journal of Medicinal Chemistry, 1998 , vol. 41, # 18 p. 3435 - 3441

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Citation Number: 22

Abstract

A series of 2-amino-9-(3-hydroxymethyl-4-alkoxycarbonyloxybut-1-yl) purines (4-10) and 2- amino-9-(2-(2-oxo-1, 3-dioxan-5-yl) ethyl) purine (1) were synthesized as potential prodrugs of penciclovir and evaluated for their oral penciclovir bioavailability in mice and rats. Treatment of 2-(2-benzyloxyethyl) propane-1, 3-diol (11) with 1, 1'-carbonyldiimidazole in THF followed by hydrogenolytic removal of the benzyl group of the resulting cyclic ...