(E)-9-(3-hydroxyprop-1-en-yl)adenine | 156518-71-7

• 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: (E)-9-(3-hydroxyprop-1-en-yl)adenine
• 英文别名: (E)-9-(3-hydroxyprop-1-enyl)adenine；(e)-9-(3-Hydroxyprop-1-en-1-yl)adenine；(E)-3-(6-aminopurin-9-yl)prop-2-en-1-ol
• CAS: 156518-71-7
• 化学式: C₈H₉N₅O
• 分子量: 191.192
• InChiKey: NCVDSBMWHMKUNU-OWOJBTEDSA-N

物化性质

• 沸点：
  528.7±60.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-9-(3-hydroxyprop-1-en-yl)adenine 在 吡啶 、 乙二醇单苯并酸酯 、 氨 、 溴 、 铜 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.25h， 生成 (+/-)-9-<1-(2-hydroxyethoxy)allyl>adenine
  参考文献：
  名称：

  Synthesis of novel 3′,4′-seco analogues of didehydro dideoxy nucleosides as potential antiviral agents

  摘要：

  Novel acyclo analogues (13,14) of didehydro dideoxy adenosine (d4A) lacking C-3'-C-4' bond were synthesized as potential anti-HIV agents. The key step involves the bromination of unsaturated isomer 6 with NBS in mono protected ethylene glycol leading to 3',4'-seco-2'-bromo-3'-hydroxl compound 11a. Activation of 3'-hydroxy group and reductive elimination of vicinal bromo tosylate gave 13 which on deprotection was converted into the target molecule 14.

  DOI：

  10.1016/s0040-4039(00)76665-2
• 作为产物：
  描述：

  (E)-9-(3-trityloxyprop-1-enyl)adenine 在 溶剂黄146 作用下， 反应 0.17h， 生成 (E)-9-(3-hydroxyprop-1-en-yl)adenine
  参考文献：
  名称：

  Synthesis of novel 3′,4′-seco analogues of didehydro dideoxy nucleosides as potential antiviral agents

  摘要：

  Novel acyclo analogues (13,14) of didehydro dideoxy adenosine (d4A) lacking C-3'-C-4' bond were synthesized as potential anti-HIV agents. The key step involves the bromination of unsaturated isomer 6 with NBS in mono protected ethylene glycol leading to 3',4'-seco-2'-bromo-3'-hydroxl compound 11a. Activation of 3'-hydroxy group and reductive elimination of vicinal bromo tosylate gave 13 which on deprotection was converted into the target molecule 14.

  DOI：

  10.1016/s0040-4039(00)76665-2

文献信息

• Synthesis and antiherpetic activity of (Z)- and (E)-9-(3-phosphonomethoxyprop-1-en-yl)adenines
  作者：A. V. Ivanov、V. L. Andronova、G. A. Galegov、M. V. Jasko

  DOI：10.1007/s11171-005-0007-7

  日期：2005.1

  9-(3-Phosphonomethoxyprop-1-en-yl)adenine (Z)- and (E)-isomers were synthesized. The stereoselectivity of double bond formation was studied by variation of sulfonyl groups. The resulting phosphonates exhibited a moderate antiherpetic activity in a culture of Vero cells infected with herpes simplex type 1 virus. The Z-isomer was shown to be more effective inhibitor of virus reproduction in the case

  合成了9-（3-膦氧基甲氧基丙-1-烯基）腺嘌呤（Z）-和（E）-异构体。通过改变磺酰基来研究双键形成的立体选择性。所得的膦酸酯在感染了单纯疱疹1型病毒的Vero细胞培养物中显示出中等的抗疱疹活性。在野生株和对阿昔洛韦有抗性的菌株中，Z-异构体均被证明是更有效的病毒繁殖抑制剂。
• Synthesis of novel 3′,4′-seco analogues of didehydro dideoxy nucleosides as potential antiviral agents
  作者：Milan Jokić、Vinko Škarić

  DOI：10.1016/s0040-4039(00)76665-2

  日期：1994.5

  Novel acyclo analogues (13,14) of didehydro dideoxy adenosine (d4A) lacking C-3'-C-4' bond were synthesized as potential anti-HIV agents. The key step involves the bromination of unsaturated isomer 6 with NBS in mono protected ethylene glycol leading to 3',4'-seco-2'-bromo-3'-hydroxl compound 11a. Activation of 3'-hydroxy group and reductive elimination of vicinal bromo tosylate gave 13 which on deprotection was converted into the target molecule 14.