Bobek M, Kavai I, De Clercq E
J Med Chem. 1987 Aug;30(8):1494-7. doi: 10.1021/jm00391a036.
5-(2,2-Difluorovinyl)uracil (IV) was synthesized from 2,4-dimethoxy-5-bromopyrimidine by sequential formylation, difluoromethylenation, and removal of the 2- and 4-methyl groups. Condensation of the trimethylsilyl derivative of IV with protected D-erythro-pentofuranosyl chloride followed by separation of anomers and deblocking gave 5-(2,2-difluorovinyl)-2'-deoxyuridine (V). Compound V was active against herpes simplex virus type 1 (HSV-1) infection as well as tumor cells transformed by the HSV-1 thymidine kinase gene.
5-(2,2-二氟乙烯基)尿嘧啶(IV)由2,4-二甲氧基-5-溴嘧啶经甲酰化、二氟亚甲基化及2-和4-甲基的去除依次反应合成。IV的三甲基硅烷基衍生物与受保护的D-赤型-戊呋喃糖基氯缩合，随后分离出异头物并脱保护，得到5-(2,2-二氟乙烯基)-2'-脱氧尿苷(V)。化合物V对1型单纯疱疹病毒(HSV-1)感染以及由HSV-1胸苷激酶基因转化的肿瘤细胞具有活性。
