((1S,4R)-4-(6-amino-9H-purin-9-yl)-1-ethynylcyclopent-2-enyloxy)methylphosphonic acid O-diphosphate | 1142816-46-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: ((1S,4R)-4-(6-amino-9H-purin-9-yl)-1-ethynylcyclopent-2-enyloxy)methylphosphonic acid O-diphosphate
• 英文别名: 4'-ethynyl-cd4AP diphosphate
• CAS: 1142816-46-3
• 化学式: C₁₃H₁₆N₅O₁₀P₃
• 分子量: 495.219
• InChiKey: XHSJZPQZKIGEKG-TVQRCGJNSA-N

物化性质

• 沸点：
  831.8±75.0 °C(predicted)
• 密度：
  2.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  ((1S,4R)-4-(6-amino-9H-purin-9-yl)-1-ethynylcyclopent-2-enyloxy)methylphosphonic acid O-diphosphate 在 喹啉 、 Lindlar's catalyst 、 氢气 作用下， 以 水 为溶剂， 反应 16.0h， 以15.4 mg的产率得到((1S,4R)-4-(6-amino-9H-purin-9-yl)-1-vinyl-cyclopent-2-enyloxy)methylphosphonic acid O-diphosphate
  参考文献：
  名称：

  Design, synthesis, and anti-HIV activity of 4′-modified carbocyclic nucleoside phosphonate reverse transcriptase inhibitors

  摘要：

  A diphosphate of a novel cyclopentyl based nucleoside phosphonate with potent inhibition of HIV reverse transcriptase (RT) (20, IC(50) = 0.13 mu M) has been discovered. In cell culture the parent phosphonate diacid 9 demonstrated antiviral activity EC(50) = 16 mu M, within two-fold of GS-9148, a prodrug of which is currently under clinical investigation, and within 5-fold of tenofovir (PMPA). In vitro cellular metabolism studies using 9 confirmed that the active diphosphate metabolite is produced albeit at a lower efficiency relative to GS-9148. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.028
• 作为产物：
  描述：

  ((1S,4R)-4-(6-amino-9H-purin-9-yl)-1-ethynylcyclopent-2-enyloxy)methylphosphonic acid diammonium salt 生成 ((1S,4R)-4-(6-amino-9H-purin-9-yl)-1-ethynylcyclopent-2-enyloxy)methylphosphonic acid O-diphosphate
  参考文献：
  名称：

  Design, synthesis, and anti-HIV activity of 4′-modified carbocyclic nucleoside phosphonate reverse transcriptase inhibitors

  摘要：

  A diphosphate of a novel cyclopentyl based nucleoside phosphonate with potent inhibition of HIV reverse transcriptase (RT) (20, IC(50) = 0.13 mu M) has been discovered. In cell culture the parent phosphonate diacid 9 demonstrated antiviral activity EC(50) = 16 mu M, within two-fold of GS-9148, a prodrug of which is currently under clinical investigation, and within 5-fold of tenofovir (PMPA). In vitro cellular metabolism studies using 9 confirmed that the active diphosphate metabolite is produced albeit at a lower efficiency relative to GS-9148. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.028