5-(bromomethyl)-2,4-dimethylpyridin-3-ol hydrobromide | 98489-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(bromomethyl)-2,4-dimethylpyridin-3-ol hydrobromide
• 英文别名: 5-Brommethyl-2,4-dimethyl-pyridin-3-ol; Hydrobromid；2,4-DimethyL3-hydroxy-5-brommethylpyridin-hydrobromid；5-(bromomethyl)-2,4-dimethylpyridin-3-ol;hydrobromide
• CAS: 98489-02-2
• 化学式: BrH*C₈H₁₀BrNO
• 分子量: 296.989
• InChiKey: NAWWFKIKJVOAFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  33.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(bromomethyl)-2,4-dimethylpyridin-3-ol hydrobromide 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以15.8 g的产率得到5-(azidomethyl)-2,4-dimethylpyridin-3-ol hydrochloride
  参考文献：
  名称：

  Rational Design of Novel Pyridinol-Fused Ring Acetaminophen Analogues

  摘要：

  Acetaminophen (ApAP) is an electron donor capable of reducing radicals generated by redox cycling of hemeproteins. It acts on the prostaglandin H synthases (cyclooxygenases; COXs) to reduce the protoporphyrin radical cation in the peroxidase site of the enzyme, thus preventing the intramolecular electron transfer that generates the Tyr385 radical required for abstraction of a hydrogen from arachidonic acid to initiate prostaglandin synthesis. Unrelated to this pharmacological action, metabolism of ApAP by CYPs yields an iminoquinone electrophile that is responsible for the hepatotoxicity, which results from high doses of the drug. We synthesized novel heterocyclic phenols predicted to be electron donors. Two of these inhibited the oxygenation of arachidonic acid by PGHS-1 and myoglobin and also were shown to be more metabolically stable and exhibited less direct cytotoxicity than acetaminophen. They are leading candidates for studies to determine whether they are free of the metabolism-based hepatotoxicity produced by acetaminophen.

  DOI：

  10.1021/ml4000904
• 作为产物：
  描述：

  4-脱氧吡哆醇盐酸盐 在 氢溴酸 作用下， 反应 0.33h， 生成 5-(bromomethyl)-2,4-dimethylpyridin-3-ol hydrobromide
  参考文献：
  名称：

  Rational Design of Novel Pyridinol-Fused Ring Acetaminophen Analogues

  摘要：

  Acetaminophen (ApAP) is an electron donor capable of reducing radicals generated by redox cycling of hemeproteins. It acts on the prostaglandin H synthases (cyclooxygenases; COXs) to reduce the protoporphyrin radical cation in the peroxidase site of the enzyme, thus preventing the intramolecular electron transfer that generates the Tyr385 radical required for abstraction of a hydrogen from arachidonic acid to initiate prostaglandin synthesis. Unrelated to this pharmacological action, metabolism of ApAP by CYPs yields an iminoquinone electrophile that is responsible for the hepatotoxicity, which results from high doses of the drug. We synthesized novel heterocyclic phenols predicted to be electron donors. Two of these inhibited the oxygenation of arachidonic acid by PGHS-1 and myoglobin and also were shown to be more metabolically stable and exhibited less direct cytotoxicity than acetaminophen. They are leading candidates for studies to determine whether they are free of the metabolism-based hepatotoxicity produced by acetaminophen.

  DOI：

  10.1021/ml4000904

文献信息

• Herstellung von Derivaten des Pyridoxins, insbesondere dessen Schwefelanaloga
  作者：Selma Kreisky

  DOI：10.1007/bf00902522

  日期：——
• Sakuragi; Kummerow, Archives of Biochemistry, 1957, vol. 71, p. 303,304
  作者：Sakuragi、Kummerow

  DOI：——

  日期：——
• Thiuroniumderivate der Pyridoxingruppe
  作者：Selma Kreisky

  DOI：10.1007/bf00901693

  日期：——