9-[(1'R,2'S,3'R,4'R)-2',3'-dihydroxy-4'-(hydroxymethyl)cyclopentyl]-2-vinyl-1H-purin-6(9H)-one | 1203452-19-0

• 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: 9-[(1'R,2'S,3'R,4'R)-2',3'-dihydroxy-4'-(hydroxymethyl)cyclopentyl]-2-vinyl-1H-purin-6(9H)-one
• 英文别名: 2-vinylinosine；9-[(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-2-ethenyl-1H-purin-6-one
• CAS: 1203452-19-0
• 化学式: C₁₃H₁₆N₄O₄
• 分子量: 292.294
• InChiKey: ZPDNXAMWEWCLKG-CCXSFMJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-[(1'R,2'S,3'R,4'R)-2',3'-dihydroxy-4'-(hydroxymethyl)cyclopentyl]-2-vinyl-1H-purin-6(9H)-one 生成
  参考文献：
  名称：

  Impdh As A Biological Probe For Rna Antiviral Drug Discovery: Synthesis, Enzymology, Molecular Docking, And Antiviral Activity Of New Ribonucleosides With Surrogate Bases

  摘要：

  Our interest in the discovery of molecules with antiviral activity against RNA viruses led us to the design of ribonucleosides with surrogate bases with the intent Of using inhibition of inosine monophosphate dehydrogenase (IMPDH) as a probe for antiviral drug discovery. A general methodology for the preparation of these compounds is discussed. Kinetic parameters of the inhibition studies with IMPDH, which were carried out spectrophotometrically by monitoring the formation of NADH, are given. Antiviral information and correlation of activity with IMPDH inhibition are discussed.

  DOI：

  10.1080/15257770701490506
• 作为产物：
  描述：

  在 氨 作用下， 以 甲醇 为溶剂， 生成 9-[(1'R,2'S,3'R,4'R)-2',3'-dihydroxy-4'-(hydroxymethyl)cyclopentyl]-2-vinyl-1H-purin-6(9H)-one
  参考文献：
  名称：

  Impdh As A Biological Probe For Rna Antiviral Drug Discovery: Synthesis, Enzymology, Molecular Docking, And Antiviral Activity Of New Ribonucleosides With Surrogate Bases

  摘要：

  Our interest in the discovery of molecules with antiviral activity against RNA viruses led us to the design of ribonucleosides with surrogate bases with the intent Of using inhibition of inosine monophosphate dehydrogenase (IMPDH) as a probe for antiviral drug discovery. A general methodology for the preparation of these compounds is discussed. Kinetic parameters of the inhibition studies with IMPDH, which were carried out spectrophotometrically by monitoring the formation of NADH, are given. Antiviral information and correlation of activity with IMPDH inhibition are discussed.

  DOI：

  10.1080/15257770701490506

文献信息

• Base-Functionalized Carbocyclic Nucleosides: Design, Synthesis, and Mechanism of Antiviral Activity
  作者：Vasu Nair、Fan Zhang、Xiaohui Ma、Eric Bonsu

  DOI：10.1080/15257770903044465

  日期：2009.8.11

  nucleobase were designed as potential RNA antiviral compounds. The design was based on the expectation that the monophosphates of these compounds would be inhibitors of the enzyme, IMPDH. Appropriate methodologies were developed to achieve the target molecules. Results from the initial in vitro antiviral studies are mentioned. The IMPDH-associated mechanism of the antiviral activity of the most active

  在核碱基的 C-2 位置具有不饱和基团的新碳环核糖核苷被设计为潜在的 RNA 抗病毒化合物。该设计基于预期这些化合物的单磷酸盐将成为酶 IMPDH 的抑制剂。开发了适当的方法来实现目标分子。提到了最初的体外抗病毒研究的结果。酶抑制研究支持了最活跃化合物抗病毒活性的 IMPDH 相关机制。