Journal
CARBOHYDRATE RESEARCH
Volume 342, Issue 6, Pages 865-869Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2007.01.004
Keywords
carbocyclic azole nucleoside; D-pinitol; 1,2,4-triazole; benzotriazole; nitroindazole; opening of epoxy ring reaction; antitumor activity
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A convenient strategy is reported for the synthesis of azole nucleoside analogues of D-pinitol (=3-O-methyl-D-chiro-inositol). The key intermediate 3-O-methyl-4,5-epoxy-D-chiro-inositol was obtained in excellent yield via an epoxidation from monomethanesulfonate Of D-pinitol. The process of opening of the epoxy ring by azole-bases appeared strongly regioselective in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene. All newly synthesized carbocyclic azole nucleosides were assayed against lung and bladder cancer in vitro. Only the triazole and benzotriazole nucleoside analogues inhibited the growth of human lung cancer cell lines (PG) with EC(50) of 11.3 and 22.6 mu M, respectively, and showed much less inhibitory activity against human bladder cell lines (T(24)). (c) 2007 Elsevier Ltd. All rights reserved.
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