2-ethynyl-9-(β-D-ribofuranosyl)hypoxanthine | 582304-98-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-ethynyl-9-(β-D-ribofuranosyl)hypoxanthine
• 英文别名: 2-ethynylinosine；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-ethynyl-1H-purin-6-one；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-ethynyl-1H-purin-6-one
• CAS: 582304-98-1
• 化学式: C₁₂H₁₂N₄O₅
• 分子量: 292.251
• InChiKey: RGNYTWVYFLRQGR-JJNLEZRASA-N

物化性质

• 熔点：
  224-228 °C
• 沸点：
  719.9±70.0 °C(Predicted)
• 密度：
  1.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-ethynyl-9-(β-D-ribofuranosyl)hypoxanthine 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：

  2',3',5'-三-O-乙酰-6-氯-2-碘嘌呤核苷 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氨 、 三乙胺 、 adenosine deaminase 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 为溶剂， 反应 54.0h， 生成 2-ethynyl-9-(β-D-ribofuranosyl)hypoxanthine
  参考文献：
  名称：

  2-官能化嘌呤核苷的合成和生物活性。

  摘要：

  使用合成方法的新应用已经制备了在2位功能化的新型嘌呤核苷。将靶分子设计为该酶，肌苷单磷酸脱氢酶（IMPDH）的潜在抑制剂（作为其单磷酸盐），并提供代表性的抑制数据。讨论了化合物的抗病毒数据。

  DOI：

  10.1081/ncn-120019498

文献信息

• Impdh As A Biological Probe For Rna Antiviral Drug Discovery: Synthesis, Enzymology, Molecular Docking, And Antiviral Activity Of New Ribonucleosides With Surrogate Bases
  作者：Vasu Nair、Xiaohui Ma、Qingning Shu、Fan Zhang、Vinod Uchil、Govardhan R. Cherukupalli

  DOI：10.1080/15257770701490506

  日期：2007.11.26

  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.
• Synthesis and Biological Activities of 2-Functionalized Purine Nucleosides
  作者：Vasu Nair、Bindu Bera、Earl R. Kern

  DOI：10.1081/ncn-120019498

  日期：2003.5

  Novel purine nucleosides functionalized at the 2-position have been prepared using new applications of synthetic methodology. The target molecules were designed as potential inhibitors (as their monophosphates) of the enzyme, inosine monophosphate dehydrogenase (IMPDH), and representative inhibition data are presented. Antiviral data of the compounds are discussed.

  使用合成方法的新应用已经制备了在2位功能化的新型嘌呤核苷。将靶分子设计为该酶，肌苷单磷酸脱氢酶（IMPDH）的潜在抑制剂（作为其单磷酸盐），并提供代表性的抑制数据。讨论了化合物的抗病毒数据。