Montgomery J A, Shortnacy A T, Carson D A, Secrist J A
J Med Chem. 1986 Nov;29(11):2389-92. doi: 10.1021/jm00161a041.
The synthesis of 9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)guanine (1b) from 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-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 1b results in an inhibition of DNA synthesis as judged by the reduced incorporation of labeled thymidine into DNA, while RNA and protein syntheses were unaffected.
报道了以1,3 - 二 - O - 乙酰基 - 5 - O - 苯甲酰基 - 2 - 脱氧 - 2 - 氟 - D - 阿拉伯呋喃糖（2a）和2,6 - 二氯嘌呤为原料，经六步反应合成9 -（2 - 脱氧 - 2 - 氟 - β - D - 阿拉伯呋喃糖基）鸟嘌呤（1b），最后一步采用酶促脱氨反应。发现目标化合物对嘌呤核苷磷酸化酶的切割稳定，并且在两种细胞系中具有细胞毒性，其中一种是T细胞系。用1b孵育L1210细胞会导致DNA合成受到抑制，这通过标记的胸苷掺入DNA减少来判断，而RNA和蛋白质合成不受影响。
