1-(3-Benzyloxy-phenyl)-[1,2,4]triazinan-3-one | 122611-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3-Benzyloxy-phenyl)-[1,2,4]triazinan-3-one
• 英文别名: 1-(3-phenylmethoxyphenyl)-1,2,4-triazinan-3-one
• CAS: 122611-62-5
• 化学式: C₁₆H₁₇N₃O₂
• 分子量: 283.33
• InChiKey: QBNPKBSDIQFROU-UHFFFAOYSA-N

物化性质

• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-Benzyloxy-phenyl)-[1,2,4]triazinan-3-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以60%的产率得到1-(3-Hydroxy-phenyl)-[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
• 作为产物：
  描述：

  3-苄氧基苯胺 在 盐酸 、 乙基溴化镁 、 溶剂黄146 、 N,N-二异丙基乙胺 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 75.5h， 生成 1-(3-Benzyloxy-phenyl)-[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

• 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
• 5-Lipoxygenase Inhibitors:  Synthesis and Structure−Activity Relationships of a Series of 1-Aryl-2<i>H</i>,4<i>H</i>-tetrahydro-1,2,4-triazin-3-ones
  作者：Pramila A. Bhatia、Clint D. W. Brooks、Anwer Basha、James D. Ratajczyk、Bruce P. Gunn、Jennifer B. Bouska、Carmine Lanni、Patrick R. Young、Randy L. Bell、George W. Carter

  DOI：10.1021/jm960372b

  日期：1996.1.1

  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.