9-(2-Deoxy-2-fluoro-. beta.-D-arabinofuranosyl) guanine: a metabolically stable cytotoxic analogue of 2'-deoxyguanosine

JA Montgomery, AT Shortnacy, DA Carson…

Index: Montgomery; Shortnacy; Carson; Secrist III Journal of Medicinal Chemistry, 1986 ,  vol. 29,  # 11  p. 2389 - 2392

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Citation Number: 44

Abstract

The synthesis of 9-(2-deoxy-2-fluoro-@-~-arabinofuranosyl) guanine (lb) from 1, 3-di-0- acetyl-5-0-benzoyl-2-deoxy-2-fluoro-~-arabinofuranose (2a) and 2, 6-dichloropurine in six steps using an enzymatic deamination as the last step is reported. The target compound was found to be stable to purine nucleoside phosphorylase cleavage and was cytotoxic in two cell lines, one a T-cell line. Incubation of L1210 cells with Ib results in an inhibition of DNA ...