2-乙基-4-吡啶-3-基酞嗪-1-酮 | 137381-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-乙基-4-吡啶-3-基酞嗪-1-酮
• 中文别名: 2-噻吩甲酰胺并,N-(4-碘苯基)-
• 英文名称: 2-ethyl-4-(3-pyridyl)-1(2H)-phthalazinone
• 英文别名: 2-ethyl-4-pyridin-3-ylphthalazin-1-one
• CAS: 137381-66-9
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: SSNUPBSCHCYXHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2-羧基苯基)-(吡啶-3-基)-酮 在 sodium hydride 、 肼 作用下， 反应 3.5h， 生成 2-乙基-4-吡啶-3-基酞嗪-1-酮
  参考文献：
  名称：

  Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 2. 4-(3-Pyridyl)-1(2H)-phthalazinones

  摘要：

  A series of novel 4-(3-pyridyl)-1(2H)-phthalazinone derivatives which possess dual activities of thromboxane A(2) (TXA(2)) synthetase inhibition and bronchodilation was synthesized, and their pharmacological activities were evaluated. While the length and the built of 2-alkyl substituents had no influence on either activity, the 2-substituents with polar groups reduced bronchodilatory activity. Furthermore, we introduced heteroaromatic nuclei into the 4-position of the phthalazinone and found that 1-imidazolyl (13a) and 5-thiazolyl (16b and 16c) derivatives were as active as the parent 3-pyridyl compound 5b. These findings suggest that heteroaromatic nuclei at the Li-position of phthalazinones play a critical role in TXA(2) synthetase inhibition, Additionally, the hydrophobicity of the compounds was found to exert a marked influence on bronchodilatory activity. These observations led to the selection of 2-ethyl-4-(3-pyridyl)-1 (2H)-phthalazinone (5b) (KK-505) and 2-methyl-4-(5-thiazolyl)-1(2H)-phthalazinone (16b) (KK-562) for further studies. Although their precise mechanism of action remains unclear, this series of novel phthalazinone derivatives represents a new class of antiasthma agents with dual activities.

  DOI：

  10.1021/jm00077a009

文献信息

• Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 2. 4-(3-Pyridyl)-1(2H)-phthalazinones
  作者：Masahisa Yamaguchi、Kenshi Kamei、Takaki Koga、Michitaka Akima、Akinori Maruyama、Toshio Kuroki、Nobuhiro Ohi

  DOI：10.1021/jm00077a009

  日期：1993.12

  A series of novel 4-(3-pyridyl)-1(2H)-phthalazinone derivatives which possess dual activities of thromboxane A(2) (TXA(2)) synthetase inhibition and bronchodilation was synthesized, and their pharmacological activities were evaluated. While the length and the built of 2-alkyl substituents had no influence on either activity, the 2-substituents with polar groups reduced bronchodilatory activity. Furthermore, we introduced heteroaromatic nuclei into the 4-position of the phthalazinone and found that 1-imidazolyl (13a) and 5-thiazolyl (16b and 16c) derivatives were as active as the parent 3-pyridyl compound 5b. These findings suggest that heteroaromatic nuclei at the Li-position of phthalazinones play a critical role in TXA(2) synthetase inhibition, Additionally, the hydrophobicity of the compounds was found to exert a marked influence on bronchodilatory activity. These observations led to the selection of 2-ethyl-4-(3-pyridyl)-1 (2H)-phthalazinone (5b) (KK-505) and 2-methyl-4-(5-thiazolyl)-1(2H)-phthalazinone (16b) (KK-562) for further studies. Although their precise mechanism of action remains unclear, this series of novel phthalazinone derivatives represents a new class of antiasthma agents with dual activities.