(2S,3R,4S,5R)-2-azido-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(iodomethyl)tetrahydrofuran-3-ol | 1345193-44-3

• 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: (2S,3R,4S,5R)-2-azido-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(iodomethyl)tetrahydrofuran-3-ol
• CAS: 1345193-44-3
• 化学式: C₁₁H₉ClFIN₆O₂
• 分子量: 438.587
• InChiKey: PWJMXMHJLZUTEK-JRPBRRGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  108.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R)-2-azido-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(iodomethyl)tetrahydrofuran-3-ol 在 4-二甲氨基吡啶 、 dipotassium hydrogenphosphate 、 四丁基硫酸氢铵 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 41.08h， 生成 (2R,3R,4S,5R)-2-azido-4-fluoro-2-(hydroxymethyl)-5-(4-methoxy-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Synthesis and anti-HIV-1 activity of 4-substituted-7-(2′-deoxy-2′-fluoro-4′-azido-β-d-ribofuranosyl)pyrrolo[2,3-d]pyrimidine analogues

  摘要：

  Three novel 4-subsituted-7-(2'-deoxy-2'-fluoro-4'-azido-beta-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine analogues were designed, synthesized, and tested for their anti-HIV-1 activity. Initial biological studies indicated that among these pyrrolo[2,3-d] pyrimidine ribonucleoside analogues, 4-amino-7-(2'-deoxy-2'- fluoro-4'-azido-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 10 exhibited the most potent anti-HIV-1 activity (EC50 = 0.5 +/- 0.3 mu M), while 4-hydroxy-7-(2'-deoxy-2'-fluoro-4'-azido-beta-D-ribofuranosyl)pyrrolo[ 2,3-d]pyrimidine 9 and 4-amino-5-fluoro-7-(2'-deoxy-2'-fluoro-4'-azido-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 11 showed moderate activity (EC50 = 13 +/- 8 and 5.4 +/- 0.3 mu M, respectively). The cytotoxicity of these compounds has also been assessed. No significant cytotoxicities were found for any of these compounds with concentrations up to 25 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.040
• 作为产物：
  描述：

  (3R,4S,5R)-5-(4-chloropyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-methylideneoxolan-3-ol 在 sodium azide 、 一氯化碘 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以89%的产率得到(2S,3R,4S,5R)-2-azido-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(iodomethyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Synthesis and anti-HIV-1 activity of 4-substituted-7-(2′-deoxy-2′-fluoro-4′-azido-β-d-ribofuranosyl)pyrrolo[2,3-d]pyrimidine analogues

  摘要：

  Three novel 4-subsituted-7-(2'-deoxy-2'-fluoro-4'-azido-beta-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine analogues were designed, synthesized, and tested for their anti-HIV-1 activity. Initial biological studies indicated that among these pyrrolo[2,3-d] pyrimidine ribonucleoside analogues, 4-amino-7-(2'-deoxy-2'- fluoro-4'-azido-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 10 exhibited the most potent anti-HIV-1 activity (EC50 = 0.5 +/- 0.3 mu M), while 4-hydroxy-7-(2'-deoxy-2'-fluoro-4'-azido-beta-D-ribofuranosyl)pyrrolo[ 2,3-d]pyrimidine 9 and 4-amino-5-fluoro-7-(2'-deoxy-2'-fluoro-4'-azido-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 11 showed moderate activity (EC50 = 13 +/- 8 and 5.4 +/- 0.3 mu M, respectively). The cytotoxicity of these compounds has also been assessed. No significant cytotoxicities were found for any of these compounds with concentrations up to 25 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.040