Kozai S, Maruyama T, Kimura T, Yamamoto I
Institute of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Chem Pharm Bull (Tokyo). 2001 Sep;49(9):1185-8. doi: 10.1248/cpb.49.1185.
Reaction of tri-O-acetyluridine (1) with benzyl bromide or 2-chloroacetophenone in the presence of K2CO3 gave the N3-substituted analogues 2a,c. Condensation of 1 with (+/-)-1-phenylethanol or 3,5-dimethylbenzyl alcohol using the Mitsunobu reaction also gave 2b,d in good yields. These compounds were allowed to react with Lawesson's reagent and were subsequently treated with ammonia to afford the 4-thiouracil derivatives 5a-d. Compounds 5a-c showed moderate hypnotic activity in mice. However, N3-(3,5-dimethyl)benzyl derivatives 3d, 5d were found to be almost inactive in this assay.
三 - O - 乙酰尿苷（1）在碳酸钾存在下与苄基溴或2 - 氯苯乙酮反应，得到N3 - 取代类似物2a、c。使用 Mitsunobu 反应使1与（±）-1 - 苯乙醇或3,5 - 二甲基苄醇缩合，也以良好产率得到2b、d。使这些化合物与劳森试剂反应，随后用氨处理，得到4 - 硫代尿嘧啶衍生物5a - d。化合物5a - c在小鼠中显示出中等催眠活性。然而，发现N3 - （3,5 - 二甲基）苄基衍生物3d、5d在此测定中几乎无活性。
