[(2R,3S,5R)-5-[5-iodo-3-(4-methylbenzoyl)-2,4-dioxopyrimidin-1-yl]-3-(4-methylbenzoyl)oxythiolan-2-yl]methyl 4-methylbenzoate | 174357-88-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(2R,3S,5R)-5-[5-iodo-3-(4-methylbenzoyl)-2,4-dioxopyrimidin-1-yl]-3-(4-methylbenzoyl)oxythiolan-2-yl]methyl 4-methylbenzoate
• CAS: 174357-88-1
• 化学式: C₃₃H₂₉IN₂O₇S
• 分子量: 724.573
• InChiKey: CNLJCIDUWSMNQR-UPRLRBBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-5-[5-iodo-3-(4-methylbenzoyl)-2,4-dioxopyrimidin-1-yl]-3-(4-methylbenzoyl)oxythiolan-2-yl]methyl 4-methylbenzoate 在 四(三苯基膦)钯 、 sodium methylate 作用下， 以 甲醇 、 六甲基磷酰三胺 为溶剂， 反应 19.5h， 生成 2'-deoxy-4'-thio-5-vinyluridine
  参考文献：
  名称：

  Synthesis and Anti-Herpes Virus Activity of 2‘-Deoxy-4‘-thiopyrimidine Nucleosides

  摘要：

  A series of 5-substituted 2'-deoxy-4'-thiopyrimidine nucleosides was synthesized and evaluated as potential antiviral agents. A number of analogues such as 2'-deoxy-5-propyl-4'-thiouridine (3ii), 2'-deoxy-5-isopropyl-4'-thiouridine (3iii), 5-cyclopropyl-2'-deoxy-4'-thiouridine (3iv), 2'-deoxy-4'-thio-5-vinyluridine (3viii), and 5-(2-chloroethyl)-2'-deoxy-4'-thiouridin (3xx) were found to be highly active against herpes simplex virus type-1 (HSV-1) and varicella tester virus (VZV) in vitro with no significant cytotoxicity. The compound with the broadest spectrum of activity was 2'-deoxy-5-ethyl-4'-thiouridine (3i) which showed significant activity against HSV-1, HSV-2, and VZV.

  DOI：

  10.1021/jm950029r
• 作为产物：
  描述：

  对甲基苯甲酰氯 、 2'-deoxy-5-iodo-4'-thiouridine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 反应 5.0h， 以87%的产率得到[(2R,3S,5R)-5-[5-iodo-3-(4-methylbenzoyl)-2,4-dioxopyrimidin-1-yl]-3-(4-methylbenzoyl)oxythiolan-2-yl]methyl 4-methylbenzoate
  参考文献：
  名称：

  Synthesis and Anti-Herpes Virus Activity of 2‘-Deoxy-4‘-thiopyrimidine Nucleosides

  摘要：

  A series of 5-substituted 2'-deoxy-4'-thiopyrimidine nucleosides was synthesized and evaluated as potential antiviral agents. A number of analogues such as 2'-deoxy-5-propyl-4'-thiouridine (3ii), 2'-deoxy-5-isopropyl-4'-thiouridine (3iii), 5-cyclopropyl-2'-deoxy-4'-thiouridine (3iv), 2'-deoxy-4'-thio-5-vinyluridine (3viii), and 5-(2-chloroethyl)-2'-deoxy-4'-thiouridin (3xx) were found to be highly active against herpes simplex virus type-1 (HSV-1) and varicella tester virus (VZV) in vitro with no significant cytotoxicity. The compound with the broadest spectrum of activity was 2'-deoxy-5-ethyl-4'-thiouridine (3i) which showed significant activity against HSV-1, HSV-2, and VZV.

  DOI：

  10.1021/jm950029r