diethyl [(Z)-5-(2-amino-6-chloro-9H-9-purinyl)-1,1-difluoro-2-pentenyl]phosphonate | 220167-00-0

• 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: diethyl [(Z)-5-(2-amino-6-chloro-9H-9-purinyl)-1,1-difluoro-2-pentenyl]phosphonate
• CAS: 220167-00-0
• 化学式: C₁₄H₁₉ClF₂N₅O₃P
• 分子量: 409.76
• InChiKey: VJHGVUCXLXDLGU-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105.15
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diethyl [(Z)-5-(2-amino-6-chloro-9H-9-purinyl)-1,1-difluoro-2-pentenyl]phosphonate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 71.0h， 以75%的产率得到[(Z)-5-(2-Amino-6-oxo-1,6-dihydro-purin-9-yl)-1,1-difluoro-pent-2-enyl]-phosphonic acid
  参考文献：
  名称：

  Synthesis of 1,1-difluoro-5-(1H-9-purinyl)-2-pentenylphosphonic acids and the related methano analogues. Remarkable effect of the nucleobases and the cyclopropane rings on inhibitory activity toward purine nucleoside phosphorylase

  摘要：

  A series of 1,1-difluoro-5-(1H-9-purinyl)-2-pentenylphosphonic acids, (E)-2a,b and (Z)-2a,b, as well as the related methano analogues (+/-)-3a,b and (+/-)-4a,b were prepared for evaluation of their PNP inhibitory activities. The cyclopopane ring and the hypoxanthine residue were found to increase the profile of inhibitory activity. The IC50 and K-i values of difluoro({1R*,2S*)-2-[2-(6-oxo-6,9-dihydro-1H-9-purinyl)ethyl]cyclopropyl)methylphosphonic acid (+/-)3b toward PNP purified from Cellulomonas sp. were determined to be 70 nM and 8.8 nM, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)80023-0
• 作为产物：
  描述：

  diethyl [(Z)-1,1-difluoro-5-hydroxy-2-pentenyl]phosphonate 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 diethyl [(Z)-5-(2-amino-6-chloro-9H-9-purinyl)-1,1-difluoro-2-pentenyl]phosphonate
  参考文献：
  名称：

  Synthesis of 1,1-difluoro-5-(1H-9-purinyl)-2-pentenylphosphonic acids and the related methano analogues. Remarkable effect of the nucleobases and the cyclopropane rings on inhibitory activity toward purine nucleoside phosphorylase

  摘要：

  A series of 1,1-difluoro-5-(1H-9-purinyl)-2-pentenylphosphonic acids, (E)-2a,b and (Z)-2a,b, as well as the related methano analogues (+/-)-3a,b and (+/-)-4a,b were prepared for evaluation of their PNP inhibitory activities. The cyclopopane ring and the hypoxanthine residue were found to increase the profile of inhibitory activity. The IC50 and K-i values of difluoro({1R*,2S*)-2-[2-(6-oxo-6,9-dihydro-1H-9-purinyl)ethyl]cyclopropyl)methylphosphonic acid (+/-)3b toward PNP purified from Cellulomonas sp. were determined to be 70 nM and 8.8 nM, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)80023-0