9-(2,3-dihydroxypropyl)-6-(pyrrol-1-yl)purine | 176108-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-(2,3-dihydroxypropyl)-6-(pyrrol-1-yl)purine
• 英文别名: 3-(6-Pyrrol-1-ylpurin-9-yl)propane-1,2-diol
• CAS: 176108-88-6
• 化学式: C₁₂H₁₃N₅O₂
• 分子量: 259.268
• InChiKey: GZQIHBUDYWTUKH-UHFFFAOYSA-N

物化性质

• 沸点：
  570.6±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 9-(2,3-dihydroxypropyl)-6-(pyrrol-1-yl)purine 在 吡啶 作用下， 反应 20.0h， 以95%的产率得到9-(2,3-diacetoxypropyl)-6-(N-pyrrolyl)purine
  参考文献：
  名称：

  The Novel 6–(N-Pyrrolyl)purine Acyclic Nucleosides:¹H and¹³C NMR and X-ray Structural Study†

  摘要：

  Synthesis of the novel nucleoside analogues containing exocyclic pyrrolo moiety and acyclic side chains attached to the purine ring at N-9 and N-7 is described. The site of alkylation was determined by H-1 and C-13 NMR on the basis of chemical shifts, C-H coupling constants and connectivity in NOESY and HETCOR spectra. The N-9 substitution of 7 was proved by its X-ray crystallographic analysis.

  DOI：

  10.1080/07328319608002139
• 作为产物：
  描述：

  6-(1H-pyrrol-1-yl)-1H-purine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 9-(2,3-dihydroxypropyl)-6-(pyrrol-1-yl)purine
  参考文献：
  名称：

  Synthesis and biological evaluation of the novel purine and pyrimidine nucleoside analogues containing 2,3-epoxypropyl, 3-amino-2-hydroxypropyl or 2,3-epoxypropyl ether moieties

  摘要：

  The novel purine and pyrimidine nucleoside analogues possessing a 2,3-epoxypropyl (2a-2c and 8a-8c), 2,3-epoxypropyl ether (3), or 3-amino-2-hydroxypropyl (4a-6c and 9a-9c) moiety bonded at either N-9 of the C-6 substituted purine ring or N-1 and N-3 of the pyrimidine ring, were prepared and evaluated on their antitumour and antiviral activities. Compounds 3, 6b, 8b and sc showed marked inhibition of growth of human tumour cell lines (MiaPaCa(2) and Raji), whilst the inhibitory effect of 6b was greater against Raji cells than to the MiaPaCa2 ones. No specific activity of compounds 2a-3, 4a-6c and 9a-9c against HSV and VZV was detected. The compound 6b was slightly active against the replication of HIV 1 (IIIB), while 2a-2c and 8a-8c were inactive. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80090-7

文献信息

• Synthesis and biological evaluation of the novel purine and pyrimidine nucleoside analogues containing 2,3-epoxypropyl, 3-amino-2-hydroxypropyl or 2,3-epoxypropyl ether moieties
  作者：Silvana Raić-Malić、Mira Grdiša、Krešimir Pavelic、Mladen Mintas

  DOI：10.1016/s0223-5234(99)80090-7

  日期：1999.5

  The novel purine and pyrimidine nucleoside analogues possessing a 2,3-epoxypropyl (2a-2c and 8a-8c), 2,3-epoxypropyl ether (3), or 3-amino-2-hydroxypropyl (4a-6c and 9a-9c) moiety bonded at either N-9 of the C-6 substituted purine ring or N-1 and N-3 of the pyrimidine ring, were prepared and evaluated on their antitumour and antiviral activities. Compounds 3, 6b, 8b and sc showed marked inhibition of growth of human tumour cell lines (MiaPaCa(2) and Raji), whilst the inhibitory effect of 6b was greater against Raji cells than to the MiaPaCa2 ones. No specific activity of compounds 2a-3, 4a-6c and 9a-9c against HSV and VZV was detected. The compound 6b was slightly active against the replication of HIV 1 (IIIB), while 2a-2c and 8a-8c were inactive. (C) Elsevier, Paris.
• The Novel 6–(<i>N</i>-Pyrrolyl)purine Acyclic Nucleosides:¹H and¹³C NMR and X-ray Structural Study†
  作者：S. Raić、M. Pongraćić、J. Vorkapić-Furać、D. Vikić-Topić、A. Hergold-Brundić、A. Nagl、M. Mintas

  DOI：10.1080/07328319608002139

  日期：1996.4

  Synthesis of the novel nucleoside analogues containing exocyclic pyrrolo moiety and acyclic side chains attached to the purine ring at N-9 and N-7 is described. The site of alkylation was determined by H-1 and C-13 NMR on the basis of chemical shifts, C-H coupling constants and connectivity in NOESY and HETCOR spectra. The N-9 substitution of 7 was proved by its X-ray crystallographic analysis.