(1R,cis)-3-<(2-amino-6-chloropyrimidin-4-yl)aminomethyl>-1,2,2-trimethylcyclopentylmethanol | 168974-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (1R,cis)-3-<(2-amino-6-chloropyrimidin-4-yl)aminomethyl>-1,2,2-trimethylcyclopentylmethanol
• 英文别名: [(1R,3S)-3-[[(2-amino-6-chloropyrimidin-4-yl)amino]methyl]-1,2,2-trimethylcyclopentyl]methanol
• CAS: 168974-88-7
• 化学式: C₁₄H₂₃ClN₄O
• 分子量: 298.816
• InChiKey: RAVDOPFBQSJKRI-OTYXRUKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  84.06
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,cis)-3-<(2-amino-6-chloropyrimidin-4-yl)aminomethyl>-1,2,2-trimethylcyclopentylmethanol 在 盐酸 、 sodium hydroxide 、 sodium acetate 、 锌 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 11.0h， 生成 2-Amino-9-((1S,3R)-3-hydroxymethyl-2,2,3-trimethyl-cyclopentylmethyl)-9H-purin-6-ol
  参考文献：
  名称：

  Synthesis and Antiviral and Cytostatic Activities of Carbocyclic Nucleosides Incorporating a Modified Cyclopentane Ring. I: Guanosine Analogues

  摘要：

  Six new carbocyclic nucleosides were prepared by constructing a guanine (compounds 6, 8 and 10) or 8-azaguanine (compounds 7, 9 and 11) base on the amino group of (1R, cis)-3-(aminomethyl)-1,2,2-trimethylcyclopentylmethanol (2), and their activities against 13 viruses and 3 tumor cell lines were determined. Compounds 9, 10 and 11 showed activity against human immunodeficiency virus type 1 (HIV-1), and compound 11 also against vaccina virus, whereas compounds 6 and 7 showed some inhibition of tumor cell proliferation.

  DOI：

  10.1080/07328319708002530
• 作为产物：
  描述：

  2-氨基-4,6-二氯嘧啶 、 (1R,cis)-3-aminomethyl-1,2,2-trimethylcyclopentylmethanol 以 三乙胺 、 正丁醇 为溶剂， 反应 48.0h， 以72%的产率得到(1R,cis)-3-<(2-amino-6-chloropyrimidin-4-yl)aminomethyl>-1,2,2-trimethylcyclopentylmethanol
  参考文献：
  名称：

  Synthesis and Antiviral and Cytostatic Activities of Carbocyclic Nucleosides Incorporating a Modified Cyclopentane Ring. I: Guanosine Analogues

  摘要：

  Six new carbocyclic nucleosides were prepared by constructing a guanine (compounds 6, 8 and 10) or 8-azaguanine (compounds 7, 9 and 11) base on the amino group of (1R, cis)-3-(aminomethyl)-1,2,2-trimethylcyclopentylmethanol (2), and their activities against 13 viruses and 3 tumor cell lines were determined. Compounds 9, 10 and 11 showed activity against human immunodeficiency virus type 1 (HIV-1), and compound 11 also against vaccina virus, whereas compounds 6 and 7 showed some inhibition of tumor cell proliferation.

  DOI：

  10.1080/07328319708002530

文献信息

• Carbocyclic Nucleosides with a Modified Cyclopentane Skeleton
  作者：O. Caamaño、F. Fernández、G. Gómez、M. I. Nieto

  DOI：10.1080/15257779508012365

  日期：1995.5.1

  The aminoalcohol 4 has been converted into carbocyclic nucleoside analogues 2 and 3.