Schinazi R F, Chen M S, Prusoff W H
J Med Chem. 1978 Nov;21(11):1141-6. doi: 10.1021/jm00209a010.
The 5'-hydroxymethylene function of several uracil and cytosine nucleosides has been modified to produce a variety of uronic acids, uronates, uronamides, and urononitriles of 2'-deoxy-beta-D-erythro-pentofuranosyl- and beta-D-arabino-pentofuranosylpyrimidines. In addition, the 5 position in many of these nucleosides has been substituted by a halogen atom. Twenty-one of the 35 compounds synthesized and examined for biological activity have not been previously reported. The purity of the products was measured by a high-pressure liquid chromatographic method. They were then evaluated as potential growth inhibitors of murine Sarcoma 180 cells in culture, of herpes simplex virus type 1 in vitro, and of Streptococcus faecium, a folic acid or deoxythymidine dependent bacterial strain. The ability of these nucleoside analogues to inhibit the phosphorylation of deoxythymidine by herpes simplex virus type 1 encoded pyrimidine deoxyribonucleoside kinase was also investigated and a structure-activity relationship examined.
几种尿嘧啶和胞嘧啶核苷的5'-羟亚甲基官能团已被修饰，以制备多种2'-脱氧-β-D-赤型-戊呋喃糖基-和β-D-阿拉伯呋喃糖基嘧啶的糖醛酸、糖醛酸盐、糖酰胺和糖腈。此外，许多这些核苷的5位已被卤原子取代。合成并检测生物活性的35种化合物中有21种此前未见报道。产物纯度通过高压液相色谱法测定。然后，将它们评估为培养的小鼠肉瘤180细胞、体外单纯疱疹病毒1型以及粪肠球菌（一种依赖叶酸或脱氧胸苷的细菌菌株）的潜在生长抑制剂。还研究了这些核苷类似物抑制单纯疱疹病毒1型编码的嘧啶脱氧核糖核苷激酶对脱氧胸苷磷酸化的能力，并考察了构效关系。
