2-vinyl-9-(β-D-ribofuranosyl)hypoxanthine 5'-monophosphate | 185378-10-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 2-vinyl-9-(β-D-ribofuranosyl)hypoxanthine 5'-monophosphate
• 英文别名: 5'-Inosinic acid, 2-ethenyl-；[(2R,3S,4R,5R)-5-(2-ethenyl-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 185378-10-3
• 化学式: C₁₂H₁₅N₄O₈P
• 分子量: 374.247
• InChiKey: GJSWNSHGOOIJLU-JJNLEZRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  176
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2',3',5'-三-O-乙酰-6-氯-2-碘嘌呤核苷 在 双(乙腈)氯化钯(II) 、 potassium phosphate buffer 、 磷酸三乙酯 、 calf spleen adenosine deaminase 、 氨 、 三氯氧磷 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 102.0h， 生成 2-vinyl-9-(β-D-ribofuranosyl)hypoxanthine 5'-monophosphate
  参考文献：
  名称：

  Inhibition of inosine monophosphate dehydrogenase (IMPDH) by the antiviral compound, 2-vinylinosine monophosphate

  摘要：

  A new enzyme-mediated synthesis of 2-vinylinosine, a compound with broad-spectrum RNA antiviral activity, is described. In order to understand the mechanism of action of this compound, we synthesized its monophosphate and investigated the behavior of that compound toward the enzyme, inosine monophosphate dehydrogenase (IMPDH), a key enzyme involved in the biosynthesis of nucleotides. 2-Vinylinosine monophosphate is a potent inhibitor of IMPDH with a K-i of 3.98 muM (k(inact) = 2.94 x 10(-2) s(-1)). The antiviral activity of 2-vinylinosine may be explained by its cellular conversion to the monophosphate through the sequential action of PNP and HGPRT and subsequent inhibition of IMPDH by the cellularly produced 2-vinylinosine 5'-monophosphate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00247-x

文献信息

• 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.