(1S)-1-(4-amino-5-cyano-1H-pyrazol-3-yl)-1,4-dideoxy-1,4-imino-D-ribitol | 488855-81-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S)-1-(4-amino-5-cyano-1H-pyrazol-3-yl)-1,4-dideoxy-1,4-imino-D-ribitol
• 英文别名: 4-amino-5-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1H-pyrazole-3-carbonitrile
• CAS: 488855-81-8
• 化学式: C₉H₁₃N₅O₃
• 分子量: 239.234
• InChiKey: WEQSKJQMUCWLQM-WYPCVCTJSA-N

物化性质

• 沸点：
  606.1±55.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  151
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S)-1-(4-amino-5-cyano-1H-pyrazol-3-yl)-1,4-dideoxy-1,4-imino-D-ribitol 在 双氧水 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 tert-butyl (2S,3S,4R,5R)-2-(4-amino-3-carbamoyl-1H-pyrazol-5-yl)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  8-Aza-immucillins as Transition-State Analogue Inhibitors of Purine Nucleoside Phosphorylase and Nucleoside Hydrolases

  摘要：

  The 8-aza-immucillins (8-aza-9-deazapurines linked from C9 to C1 of 1,4-dideoxy-1,4-iminoribitol) have been designed as transition-state analogues of the reactions catalyzed by purine nucleoside phosphorylase and nucleoside hydrolases. Syntheses of the 8-aza-immucillin analogues of inosine and adenosine are described. They are powerful inhibitors of the target enzymes with equilibrium dissociation constants as low as 42 pM.

  DOI：

  10.1021/jm0203332
• 作为产物：
  描述：

  (1S)-2,3,5,-tri-O-acetyl-1-(5-cyano-4-nitro-1H-pyrazol-3-yl)-1,4-dideoxy-1,4-imino-N-(2,2,2,-trichloroethoxycarbonyl)-D-ribitol 在 sodium methylate 、 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 反应 0.67h， 生成 (1S)-1-(4-amino-5-cyano-1H-pyrazol-3-yl)-1,4-dideoxy-1,4-imino-D-ribitol
  参考文献：
  名称：

  8-Aza-immucillins as Transition-State Analogue Inhibitors of Purine Nucleoside Phosphorylase and Nucleoside Hydrolases

  摘要：

  The 8-aza-immucillins (8-aza-9-deazapurines linked from C9 to C1 of 1,4-dideoxy-1,4-iminoribitol) have been designed as transition-state analogues of the reactions catalyzed by purine nucleoside phosphorylase and nucleoside hydrolases. Syntheses of the 8-aza-immucillin analogues of inosine and adenosine are described. They are powerful inhibitors of the target enzymes with equilibrium dissociation constants as low as 42 pM.

  DOI：

  10.1021/jm0203332

文献信息

• 8-Aza-immucillins as Transition-State Analogue Inhibitors of Purine Nucleoside Phosphorylase and Nucleoside Hydrolases
  作者：Gary B. Evans、Richard H. Furneaux、Graeme J. Gainsford、John C. Hanson、Gregory A. Kicska、Antony A. Sauve、Vern L. Schramm、Peter C. Tyler

  DOI：10.1021/jm0203332

  日期：2003.1.1

  The 8-aza-immucillins (8-aza-9-deazapurines linked from C9 to C1 of 1,4-dideoxy-1,4-iminoribitol) have been designed as transition-state analogues of the reactions catalyzed by purine nucleoside phosphorylase and nucleoside hydrolases. Syntheses of the 8-aza-immucillin analogues of inosine and adenosine are described. They are powerful inhibitors of the target enzymes with equilibrium dissociation constants as low as 42 pM.