2-vinyl-9-(β-D-ribofuranosyl)hypoxanthine | 110851-56-4

• 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-vinyl-9-(β-D-ribofuranosyl)hypoxanthine
• 英文别名: 2-vinylinosine；2-Vinyl-9-[beta-d-ribofuranosyl]hypoxanthine；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-ethenyl-1H-purin-6-one
• CAS: 110851-56-4
• 化学式: C₁₂H₁₄N₄O₅
• 分子量: 294.267
• InChiKey: IIGNJLSNAPTWKD-JJNLEZRASA-N

物化性质

• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 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-vinyl-9-(β-D-ribofuranosyl)hypoxanthine 在 二甲基硫 、 臭氧 作用下， 生成 2-formyl-9-(β-D-ribofuranosyl)hypoxanthine
  参考文献：
  名称：

  新型不饱和嘌呤核苷

  摘要：

  描述了在2-位具有一个不饱和度的许多新型嘌呤核糖核苷的合成。这些化合物的合成中使用的两个关键反应是钯催化的交叉偶联反应和臭氧分解。这些合成转化很少用于核苷化学中。讨论了在交叉偶联反应和氟离子催化条件下烯丙基嘌呤体系向乙烯基嘌呤体系的异构化。所述的新型2-甲酰基嘌呤核苷似乎易于水合。

  DOI：

  10.1016/s0040-4020(01)89227-9
• 作为产物：
  描述：

  阿卡地新 在 咪唑 、 四丁基氟化铵 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0~265.0 ℃ 、133.32 Pa 条件下， 反应 23.5h， 生成 2-vinyl-9-(β-D-ribofuranosyl)hypoxanthine
  参考文献：
  名称：

  A Short Synthesis of 2-Vinylinosine

  摘要：

  A short and practical synthesis of 2-vinylinosine from readily available materials is described.

  DOI：

  10.1080/00397919608003623

文献信息

• PHENYL-OXAZOLYL DERIVATIVES, PREPARATION METHOD THEREOF, AND RELATED APPLICATION OF THE PHENYL-OXAZOLYL DERIVATIVES AS AN IMPDH INHIBITOR
  申请人：INSTITUTE OF MEDICINAL BIOTECHNOLOGY, CHINESE ACADEMY OF MEDICAL SCIENCES

  公开号：US20150031686A1

  公开（公告）日：2015-01-29

  Disclosed are phenyl-oxazolyl derivatives having a general formula (I), a preparation method thereof, and an application of the phenyl-oxazolyl derivatives as an inosine monophosphate dehydrogenase (IMPDH) inhibitor.

  揭示了具有一般式（I）的苯基-噁唑基衍生物，其制备方法以及将苯基-噁唑基衍生物作为肌醇单磷酸脱氢酶（IMPDH）抑制剂的应用。
• Novel approaches to functionalized nucleosides via palladium-catalyzed cross coupling with organostannanes
  作者：Vasu Nair、Gregory A. Turner、Stanley D. Chamberlain

  DOI：10.1021/ja00257a071

  日期：1987.11
• New methodologies for the synthesis of C-2 functionalized hypoxanthine nucleosides
  作者：Vasu Nair、Gregory A. Turner、Greg S. Buenger、Stanley D. Chamberlain

  DOI：10.1021/jo00248a027

  日期：1988.6
• 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.
• Rationally Designed Inhibitors of Inosine Monophosphate Dehydrogenase
  作者：Han-Zhong Zhang、Kotesvar Rao、Stephen F. Carr、Eva Papp、Kenneth Straub、John C. Wu、Josef Fried

  DOI：10.1021/jm960732v

  日期：1997.1.1

  Functionalized 2-alkyl derivatives of inosinic acid have been synthesized to serve as reversible as well as irreversible inhibitors of the human type II enzyme inosine monophosphate dehydrogenase. These compounds were designed to react with Cys-331 of the enzyme to form covalent bonds so as to interfere with the normal enzyme mechanism which involves attack of Cys-331 at C-2 of the substrate. Mass spectrometric analysis of the reaction products after enzymatic degradation confirmed the appropriateness of the inhibitor design.