1-phenyl-2H,4H-tetrahydro-1,2,4-triazin-3-one | 122610-85-9

• 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-phenyl-2H,4H-tetrahydro-1,2,4-triazin-3-one
• 英文别名: 1-Phenyl-1,2,4-triazinan-3-one
• CAS: 122610-85-9
• 化学式: C₉H₁₁N₃O
• 分子量: 177.206
• InChiKey: PBAAMDZDOAGGRJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-2H,4H-tetrahydro-1,2,4-triazin-3-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以42%的产率得到1-phenyl-2H,4H-tetrahydro-1,2,4-triazin-3-thione
  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：

  N-(2-(苯基氨基)乙基)氨基甲酸乙酯 在 盐酸 、 乙基溴化镁 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 51.5h， 生成 1-phenyl-2H,4H-tetrahydro-1,2,4-triazin-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

• New Advances in the Synthesis of Emerging Cyclic Amidrazones to Foster Bioisosterism of Azaheterocycles
  作者：Johann Leblanc、Monique Mathé‐Allainmat、Sandrine Grosse、Jérôme Guillemont、Arnaud Tessier、Jacques Lebreton

  DOI：10.1002/ejoc.202300033

  日期：2023.3.7

  constitute essential molecular units that are found in natural products, in medicinal chemistry, in materials, catalysis, and so on. This work discloses a robust method to access original cyclic amidrazones as new scaffold within an uncharted chemical space.

  氮杂杂环在自然界和合成化学中无处不在，构成了天然产物、药物化学、材料、催化等中的基本分子单元。这项工作公开了一种稳健的方法，可以在未知的化学空间中获取原始环状氨基腙作为新支架。
• 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。
• Use of Ltb4 Inhibitors for the Treatment of B-Cell Leukemias and Lymphomas
  申请人：Claesson Hans-Erik

  公开号：US20080081835A1

  公开（公告）日：2008-04-03

  The invention relates to the use of an inhibitor of the biosynthesis and/or function of LTB 4 for the manufacture of a medicament for the treatment of B-cell chronic lymphocytic leukemia (B-CLL), B-prolymphocytic leukemia (B-PLL) or B-cell lymphoma. Preferably, the inhibitor of the biosynthesis and/or function of LTB 4 is the inhibitor of 5-LO BWA4C or the inhibitor of FLAP MK-886.
• Method and composition for treating inflammatory disorders
  申请人：Pereswetoff-Morath Lena

  公开号：US20090220583A1

  公开（公告）日：2009-09-03

  There is provided homogeneous pharmaceutical compositions for the treatment of inflammatory disorders comprising an antiinflammatory and/or antihistaminic active ingredient, a polar lipid liposome and a pharmaceutically-acceptable aqueous carrier.
• Method and Composition for Treating Inflammatory Disorders
  申请人：Meda AB

  公开号：US20160166508A1

  公开（公告）日：2016-06-16

  There is provided homogeneous pharmaceutical compositions for the treatment of inflammatory disorders comprising an antiinflammatory and/or antihistaminic active ingredient, a polar lipid liposome and a pharmaceutically-acceptable aqueous carrier.