2-acetonyl-9-(β-D-ribofuranosyl)hypoxanthine | 110851-53-1

• 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-acetonyl-9-(β-D-ribofuranosyl)hypoxanthine
• 英文别名: 2-acetonylinosine；2-Acetonylinosine；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(2-oxopropyl)-1H-purin-6-one
• CAS: 110851-53-1
• 化学式: C₁₃H₁₆N₄O₆
• 分子量: 324.293
• InChiKey: WFWFSJDHDNUZFU-ZRFIDHNTSA-N

物化性质

• 密度：
  1.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-acetonyl-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-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 在 咪唑 、 palladium diacetate 、 二碘甲烷 、 碘代三甲硅烷 、 C₅H₁₁NO 、 sodium methylate 、 三正丁基甲氧基锡 、 四乙基氟化铵水合物 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 生成 2-acetonyl-9-(β-D-ribofuranosyl)hypoxanthine
  参考文献：
  名称：

  Novel approaches to functionalized nucleosides via palladium-catalyzed cross coupling with organostannanes

  摘要：

  DOI：

  10.1021/ja00257a071

文献信息

• 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
• Facile, chemoenzymatic synthesis of the potent antiviral compound, 2-acetonylinosine
  作者：Mukta Gupta、Vasu Nair

  DOI：10.1016/j.tetlet.2004.12.065

  日期：2005.2

  A facile and efficient methodology for the chemoenzymatic synthesis of the antiviral compound, 2-acetonylinosine has been developed. The present synthetic strategy, which has generality, is a dramatic improvement on the methodologies currently available for the synthesis of functionalized purine nucleosides of therapeutic interest. (C) 2004 Elsevier Ltd. All rights reserved.
• NAIR, VASU;TURNER, GREGORY A.;BUENGER, GREG S.;CHAMBERLAIN, STANLEY D., J. ORG. CHEM., 53,(1988) N 13, 3051-3057
  作者：NAIR, VASU、TURNER, GREGORY A.、BUENGER, GREG S.、CHAMBERLAIN, STANLEY D.

  DOI：——

  日期：——
• NAIR, VASU;TURNER, GREGORY A.;CHAMBERLAIN, STANLEY D., J. AMER. CHEM. SOC., 109,(1987) N 23, 7223-7224
  作者：NAIR, VASU、TURNER, GREGORY A.、CHAMBERLAIN, STANLEY D.

  DOI：——

  日期：——
• US4992427A
  申请人：——

  公开号：US4992427A

  公开（公告）日：1991-02-12