Phosphoric acid mono-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-methoxymethoxymethyl-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester | 185378-05-6

• 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: Phosphoric acid mono-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-methoxymethoxymethyl-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester
• 英文别名: 2-[(Methoxymethoxy)methyl]inosine 5'-(dihydrogen phosphate)；[(2R,3S,4R,5R)-3,4-dihydroxy-5-[2-(methoxymethoxymethyl)-6-oxo-1H-purin-9-yl]oxolan-2-yl]methyl dihydrogen phosphate
• CAS: 185378-05-6
• 化学式: C₁₃H₁₉N₄O₁₀P
• 分子量: 422.288
• InChiKey: FMYFHRQBWNECHM-ZRFIDHNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  194
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Phosphoric acid mono-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-methoxymethoxymethyl-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester 在 三氟乙酸 作用下， 反应 36.0h， 生成 Phosphoric acid mono-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxymethyl-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester
  参考文献：
  名称：

  Rationally Designed Inhibitors of Inosine Monophosphate Dehydrogenase

  摘要：

  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.

  DOI：

  10.1021/jm960732v
• 作为产物：
  描述：

  阿卡地新 在 磷酸三乙酯 、 sodium ethanolate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 42.0h， 生成 Phosphoric acid mono-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-methoxymethoxymethyl-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester
  参考文献：
  名称：

  Rationally Designed Inhibitors of Inosine Monophosphate Dehydrogenase

  摘要：

  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.

  DOI：

  10.1021/jm960732v

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.