2-羟甲基-9-[β-d-呋喃核糖基]次黄嘌呤 | 185377-94-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 2-羟甲基-9-[β-d-呋喃核糖基]次黄嘌呤
• 英文名称: 9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-hydroxymethyl-1,9-dihydro-purin-6-one
• 英文别名: 2-Hydroxymethyl-9-[beta-d-ribofuranosyl]hypoxanthine；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(hydroxymethyl)-1H-purin-6-one
• CAS: 185377-94-0
• 化学式: C₁₁H₁₄N₄O₆
• 分子量: 298.255
• InChiKey: ATYALAMOPJTHPK-TZQXKBMNSA-N

物化性质

• 密度：
  2.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  149
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-羟甲基-9-[β-d-呋喃核糖基]次黄嘌呤 在 吡啶 、 四氯化碳 、 高氯酸 、 三丁基膦 作用下， 反应 5.67h， 生成 9-{(3aR,4R,6R,6aR)-6-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-chloromethyl-1,9-dihydro-purin-6-one
  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：

  乙醇酸乙酯 、 阿卡地新 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 36.0h， 以81%的产率得到2-羟甲基-9-[β-d-呋喃核糖基]次黄嘌呤
  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.