di-tert-butyl 6-hydroxy-2-oxopyrido[2,3-d]pyrimidine-1,3(2H,4H)-dicarboxylate | 1443677-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: di-tert-butyl 6-hydroxy-2-oxopyrido[2,3-d]pyrimidine-1,3(2H,4H)-dicarboxylate
• 英文别名: ditert-butyl 6-hydroxy-2-oxo-4H-pyrido[2,3-d]pyrimidine-1,3-dicarboxylate
• CAS: 1443677-13-1
• 化学式: C₁₇H₂₃N₃O₆
• 分子量: 365.386
• InChiKey: YSNDSHABTQAVNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 6-hydroxy-2-oxopyrido[2,3-d]pyrimidine-1,3(2H,4H)-dicarboxylate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以75%的产率得到6-hydroxy-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one
  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：

  2-氨基-3-氰基吡啶 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 硼烷四氢呋喃络合物 、 ammonium acetate 、 potassium acetate 、 palladium diacetate 、 联硼酸频那醇酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 27.5h， 生成 di-tert-butyl 6-hydroxy-2-oxopyrido[2,3-d]pyrimidine-1,3(2H,4H)-dicarboxylate
  参考文献：
  名称：

  INHIBITORS OF HEMEPROTEIN-CATALYZED LIPID PEROXIDATION

  摘要：

  与哺乳动物受体内异前列腺素介导的组织损伤的预防或治疗相关的化合物、组合物和方法。

  公开号：

  US20150368241A1

文献信息

• Inhibitors of hemeprotein-catalyzed lipid peroxidation
  申请人：Vanderbilt University

  公开号：US10675285B2

  公开（公告）日：2020-06-09

  Methods and compounds for the treatment or prevention of oxidative damage in a mammalian subject. The treatment and/or prevention may be on inhibiting heme-induced lipid peroxidation. Also discloses are methods and compounds for treating or preventing isoprostane-mediated tissue damage.

  用于治疗或预防哺乳动物体内氧化损伤的方法和化合物。 这种治疗和/或预防可以是抑制血红素诱导的脂质过氧化。 还公开了用于治疗或预防异丙烷介导的组织损伤的方法和化合物。
• Inhibitors of Hemeprotein-Catalyzed Lipid Peroxidation
  申请人：Vanderbilt University

  公开号：US20160067256A1

  公开（公告）日：2016-03-10

  Methods and compounds for the treatment or prevention of oxidative damage in a mammalian subject. The treatment and/or prevention may be on inhibiting heme-induced lipid peroxidation. Also discloses are methods and compounds for treating or preventing isoprostane-mediated tissue damage.
• US9133212B1
  申请人：——

  公开号：US9133212B1

  公开（公告）日：2015-09-15
• US9545385B2
  申请人：——

  公开号：US9545385B2

  公开（公告）日：2017-01-17
• [EN] INHIBITORS OF HEMEPROTEIN-CATALYZED LIPID PEROXIDATION<br/>[FR] INHIBITEURS DE PEROXYDATION LIPIDIQUE CATALYSÉE PAR HÉMOPROTÉINE
  申请人：UNIV VANDERBILT

  公开号：WO2014124059A2

  公开（公告）日：2014-08-14

  Compounds, compositions and methods related to the prevention or treatment of isoprostane-mediated tissue damage in a mammalian subject in need thereof.