7-chloro-2-(2-methylphenyl)-4H-benzo[d][1,3]oxazin-4-one | 351980-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 7-chloro-2-(2-methylphenyl)-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 7-chloro-2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one；7-chloro-2-(2-methylphenyl)-3,1-benzoxazin-4-one
• CAS: 351980-61-5
• 化学式: C₁₅H₁₀ClNO₂
• mdl: MFCD00126207
• 分子量: 271.703
• InChiKey: RDIAVAAUQPUWMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻甲基苯甲酰氯 、 2-氨基-4-氯苯甲酸 在 吡啶 作用下， 反应 24.0h， 以62%的产率得到7-chloro-2-(2-methylphenyl)-4H-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  Synthesis and evaluation of benzoxazinone derivatives on activity of human neutrophil elastase and on hemorrhagic shock-induced lung injury in rats

  摘要：

  A new series of benzoxazinone analogs were designed, synthesized, and assayed to determine their effects on superoxide anion generation and neutrophil elastase (NE) release in formyl-L-methionyl-L-leucyl-L-phenylalanine (FMLP)-activated human neutrophils. Of these, compounds 6-10 showed a potent dual inhibitory effect on NE release and superoxide anion generation. In contrast, compounds 11-15 exhibited highly selective and potent inhibitory activities on NE release. These results indicate that the inhibitory activity on NE release in FMLP-activated human neutrophils depended on the position of chloro-substituent in the A ring. On the other hand, 13 significantly attenuated the increase in myeloperoxidase (MPO) activity and edema in the lung of rats after trauma-hemorrhagic shock. Therefore, these compounds could be developed as new NE inhibitors. (c) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.046

文献信息

• Synthesis and evaluation of benzoxazinone derivatives on activity of human neutrophil elastase and on hemorrhagic shock-induced lung injury in rats
  作者：Pei-Wen Hsieh、Huang-Ping Yu、Yi-Ju Chang、Tsong-Long Hwang

  DOI：10.1016/j.ejmech.2010.03.046

  日期：2010.7

  A new series of benzoxazinone analogs were designed, synthesized, and assayed to determine their effects on superoxide anion generation and neutrophil elastase (NE) release in formyl-L-methionyl-L-leucyl-L-phenylalanine (FMLP)-activated human neutrophils. Of these, compounds 6-10 showed a potent dual inhibitory effect on NE release and superoxide anion generation. In contrast, compounds 11-15 exhibited highly selective and potent inhibitory activities on NE release. These results indicate that the inhibitory activity on NE release in FMLP-activated human neutrophils depended on the position of chloro-substituent in the A ring. On the other hand, 13 significantly attenuated the increase in myeloperoxidase (MPO) activity and edema in the lung of rats after trauma-hemorrhagic shock. Therefore, these compounds could be developed as new NE inhibitors. (c) 2010 Elsevier Masson SAS. All rights reserved.