(+)-(1R,4S)-4-[4-chloro-7H-pyrrolo(2,3-d)pyrimidin-7-yl]-2-cyclopentene-1-methanol | 343250-93-1

• 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: (+)-(1R,4S)-4-[4-chloro-7H-pyrrolo(2,3-d)pyrimidin-7-yl]-2-cyclopentene-1-methanol
• 英文别名: [(1R,4S)-4-(4-chloropyrrolo[2,3-d]pyrimidin-7-yl)cyclopent-2-en-1-yl]methanol
• CAS: 343250-93-1
• 化学式: C₁₂H₁₂ClN₃O
• 分子量: 249.7
• InChiKey: PLOXOSFGBUBBAN-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(1R,4S)-4-[4-chloro-7H-pyrrolo(2,3-d)pyrimidin-7-yl]-2-cyclopentene-1-methanol 在 吡啶 、 叔丁基氯化镁 、 氨 作用下， 以 四氢呋喃 为溶剂， 反应 84.0h， 生成 (S)-2-{[(1R,4S)-4-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-cyclopent-2-enylmethoxy]-phenoxy-phosphorylamino}-propionic acid benzyl ester
  参考文献：
  名称：

  Phosphoramidate Protides of Carbocyclic 2′,3′‐Dideoxy‐2′,3′‐Didehydro‐7‐Deazaadenosine with Potent Activity Against HIV and HBV

  摘要：

  Synthesis of phosphoramidate protides of carbocyclic D- and L-2',3'-dideoxy-2',3' -didehydro-7-deazaadenosine by treatment of the nucleoside with phosphorochloridates in the presence of pyridine and t-BuMgCl is described. Several of these protides showed significantly improved antiviral potency over the parent nucleosides against both HIV and HBV.

  DOI：

  10.1081/ncn-200040678
• 作为产物：
  描述：

  5-烯丙基-4,6-二氯嘧啶 在 盐酸 、 ammonium chloride 、 臭氧 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 乙酸乙酯 为溶剂， 反应 52.0h， 生成 (+)-(1R,4S)-4-[4-chloro-7H-pyrrolo(2,3-d)pyrimidin-7-yl]-2-cyclopentene-1-methanol
  参考文献：
  名称：

  Phosphoramidate Protides of Carbocyclic 2′,3′‐Dideoxy‐2′,3′‐Didehydro‐7‐Deazaadenosine with Potent Activity Against HIV and HBV

  摘要：

  Synthesis of phosphoramidate protides of carbocyclic D- and L-2',3'-dideoxy-2',3' -didehydro-7-deazaadenosine by treatment of the nucleoside with phosphorochloridates in the presence of pyridine and t-BuMgCl is described. Several of these protides showed significantly improved antiviral potency over the parent nucleosides against both HIV and HBV.

  DOI：

  10.1081/ncn-200040678

文献信息

• Synthesis and Anti-HIV Evaluation of 7-Deaza Analogues of Carbovir
  作者：Michel Legraverend、Anne-Marie Aubertin、Georges Obert、Christiane Huel、Emile Bisagni

  DOI：10.1080/15257779408011865

  日期：1994.5

  Three analogues of Carbovir 1 have been synthesized and evaluated for antiviral activity in vitro. Anti-HIV-1 and anti-HIV-2 activities have been observed with 7-deaza analogues 3 and 5 of 1. Compound 5 was about ten times more potent than 3 against HIV-1 and HIV-2 on different cell lines.