(+/-)-(1α,2α,3β,5β)-3-(2-amino-4-chloro-7H-pyrrolo<2,3-d>pyrimidin-7-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol | 97643-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: (+/-)-(1α,2α,3β,5β)-3-(2-amino-4-chloro-7H-pyrrolo<2,3-d>pyrimidin-7-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol
• 英文别名: (+/-)-(1α,2α,3β,5β)-3-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol
• CAS: 97643-10-2
• 化学式: C₁₂H₁₅ClN₄O₃
• 分子量: 298.729
• InChiKey: PSIMKANWVJWBBY-YYNOVJQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117.42
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (+/-)-(1α,2α,3β,5β)-3-(2-amino-4-chloro-7H-pyrrolo<2,3-d>pyrimidin-7-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol 在 盐酸 作用下， 反应 6.0h， 以80%的产率得到(+/-)-2-amino-3,4-dihydro-7-<(1α,2α,3β,4α)-2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl>-7H-pyrrolo<2,3-d>pyrimidin-4-one
  参考文献：
  名称：

  (.+-.)-2-Amino-3,4-dihydro-7-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ones: new carbocyclic analogs of 7-deazaguanosine with antiviral activity

  摘要：

  5-Allyl-2-amino-4,6-dihydroxypyrimidine (3) was chlorinated and ozonized to yield (2-amino-4,6-dichloro-pyrimidin-5-yl)acetaldehyde (5). Acetalization of 5 with ethanol afforded a new pyrimidine intermediate 6 which can lead to 2-amino-3,4-dihydro-7-alkyl-7H-pyrrolo[2,3-d]pyrimidin-4-ones and therefore to carbocyclic analogues of 7-deazaguanosine. The 7-substituent was a cyclopentyl analogue of the arabinofuranosyl moiety in 10a, lyxofuranosyl moiety in 10b, and ribofuranosyl moiety in 10c. Compounds 10a and 10b exhibited selective inhibitory activities against the multiplication of HSV1 and HSV2 in cell culture. Repeated administration of compound 10a at 10mg/kg ip to mice infected with HSV2 increased the number of survivors and lengthened significantly the mean survival time.

  DOI：

  10.1021/jm00148a017
• 作为产物：
  描述：

  5-allyl-4,6-dichloro-2-aminopyrimidine 在 臭氧 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 、 正丁醇 为溶剂， 反应 9.5h， 生成 (+/-)-(1α,2α,3β,5β)-3-(2-amino-4-chloro-7H-pyrrolo<2,3-d>pyrimidin-7-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol
  参考文献：
  名称：

  (.+-.)-2-Amino-3,4-dihydro-7-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ones: new carbocyclic analogs of 7-deazaguanosine with antiviral activity

  摘要：

  5-Allyl-2-amino-4,6-dihydroxypyrimidine (3) was chlorinated and ozonized to yield (2-amino-4,6-dichloro-pyrimidin-5-yl)acetaldehyde (5). Acetalization of 5 with ethanol afforded a new pyrimidine intermediate 6 which can lead to 2-amino-3,4-dihydro-7-alkyl-7H-pyrrolo[2,3-d]pyrimidin-4-ones and therefore to carbocyclic analogues of 7-deazaguanosine. The 7-substituent was a cyclopentyl analogue of the arabinofuranosyl moiety in 10a, lyxofuranosyl moiety in 10b, and ribofuranosyl moiety in 10c. Compounds 10a and 10b exhibited selective inhibitory activities against the multiplication of HSV1 and HSV2 in cell culture. Repeated administration of compound 10a at 10mg/kg ip to mice infected with HSV2 increased the number of survivors and lengthened significantly the mean survival time.

  DOI：

  10.1021/jm00148a017