(+/-)-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 | 97643-12-4

• 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: (+/-)-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
• 英文别名: (+/-)-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；2-amino-7-[(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-3H-pyrrolo[2,3-d]pyrimidin-4-one
• CAS: 97643-12-4
• 化学式: C₁₂H₁₆N₄O₄
• 分子量: 280.283
• InChiKey: RCUGURHIBRRZRJ-YYNOVJQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  133
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  烯丙基丙二酸二乙酯 在 盐酸 、 五氯化磷 、 sodium ethanolate 、 臭氧 、 三乙胺 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 、 正丁醇 为溶剂， 反应 37.5h， 生成 (+/-)-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

文献信息

• (.+-.)-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
  作者：Michel Legraverend、Rose Marie Nia Ngongo-Tekam、Emile Bisagni、Aurelio Zerial

  DOI：10.1021/jm00148a017

  日期：1985.10

  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.