1-Pyridin-2-yl-[1,2,4]triazinan-3-one | 122610-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 1-Pyridin-2-yl-[1,2,4]triazinan-3-one
• 英文别名: 1,2,4-Triazin-3(2H)-one, tetrahydro-1-(2-pyridinyl)-；1-pyridin-2-yl-1,2,4-triazinan-3-one
• CAS: 122610-82-6
• 化学式: C₈H₁₀N₄O
• 分子量: 178.194
• InChiKey: QDJLAXWZNJYZPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-肼吡啶 在 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 1-Pyridin-2-yl-[1,2,4]triazinan-3-one
  参考文献：
  名称：

  5-Lipoxygenase Inhibitors:  Synthesis and Structure−Activity Relationships of a Series of 1-Aryl-2H,4H-tetrahydro-1,2,4-triazin-3-ones

  摘要：

  Synthetic routes were developed to access a variety of novel 1-aryl-2H,4H-tetrahydro-1,2,4-triazin-3-one analogs which were evaluated as 5-lipoxygenase (5-LO) inhibitors. The parent structure, 1-phenylperhydro-1,2,4-triazin-3-one (4), was found to be a selective inhibitor of 5-LO in broken cell, intact cell, and human blood assays with IC50 values of 5-21 mu M. In a rat anaphylaxis model, 4 blocked leukotriene formation with an ED(50) = 7 mg/kg when administered orally. Compound 4 exhibited selectivity for inhibition of 5-LO with little activity against related enzymes: 12-LO from human platelets, 15-LO from soybean, and cyclooxygenase (COX) from sheep seminal vesicle. In pilot subacute toxicity testing, 4 did not produce methemoglobinemia in rats (400 mg/kg po daily for 9 days) or in dogs (200 mg/kg po daily for 28 days). These results indicated that the triazinone structure provided a 5-LO inhibitor template devoid of the toxicity problems observed in the related phenidone (1) and pyridazinone (3) classes of 5-LO inhibitors. The parent compound 4 is a selective, orally bioavailable 5-LO inhibitor which can serve as a useful reference standard for in vivo pharmacological studies involving leukotriene-mediated phenonmena.

  DOI：

  10.1021/jm960372b

文献信息

• Pyridazinone, triazinone and oxapyridazinone lipoxygenase inhibiting compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0299449A2

  公开（公告）日：1989-01-18

  Pyridazinone, triazinone and oxapyridazinone compounds which are useful in inhibting lipoxygenase enzymes, particularly 5-lipoxygenase.

  可抑制脂氧合酶，特别是 5-脂氧合酶的哒嗪酮、三嗪酮和噁哒嗪酮化合物。
• US4970210A
  申请人：——

  公开号：US4970210A

  公开（公告）日：1990-11-13
• US5086052A
  申请人：——

  公开号：US5086052A

  公开（公告）日：1992-02-04