N-(3-carbethoxypropyl)-N-hydroxy-4-phenylbutyramide | 121289-75-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(3-carbethoxypropyl)-N-hydroxy-4-phenylbutyramide
• 英文别名: 4-[Hydroxy-(4-phenyl-butyryl)-amino]-butyric acid ethyl ester；ethyl 4-[hydroxy(4-phenylbutanoyl)amino]butanoate
• CAS: 121289-75-6
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: BTQJWNYKTAAGQX-UHFFFAOYSA-N

物化性质

• 沸点：
  442.2±55.0 °C(predicted)
• 密度：
  1.129±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-carbethoxypropyl)-N-hydroxy-4-phenylbutyramide 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 2.0h， 以56%的产率得到N-(3-carboxypropyl)-N-hydroxy-4-phenylbutyramide
  参考文献：
  名称：

  Differential effects of a series of hydroxamic acid derivatives on 5-lipoxygenase and cyclooxygenase from neutrophils and 12-lipoxygenase from platelets and their in vivo effects on inflammation and anaphylaxis

  摘要：

  The synthesis of a series of novel substituted hydroxamates has been described along with their profile of inhibitory activity against 5-lipoxygenase, 12-lipoxygenase, and cyclooxygenase enzymes. The structure--activity relationship suggests that future molecules could be designed to specifically inhibit one or more of these enzymes since there were definite differences in structure--activity relationships for these different enzymes. A representative number of these compounds have been tested in vivo and found to possess potent oral activity in a systemic anaphylaxis model mediated by leukotrienes and topical activity in an arachidonic acid induced inflammation model. One of these molecules, compound 20, demonstrated that a leukotriene antagonist pharmacophore can be modified such that it contains both antagonist activity and 5-lipoxygenase inhibitory activity.

  DOI：

  10.1021/jm00128a027
• 作为产物：
  描述：

  4-苯基丁酸 在 palladium on activated charcoal 、 N,N-二甲基甲酰胺 氯化亚砜 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 3.0h， 生成 N-(3-carbethoxypropyl)-N-hydroxy-4-phenylbutyramide
  参考文献：
  名称：

  Differential effects of a series of hydroxamic acid derivatives on 5-lipoxygenase and cyclooxygenase from neutrophils and 12-lipoxygenase from platelets and their in vivo effects on inflammation and anaphylaxis

  摘要：

  The synthesis of a series of novel substituted hydroxamates has been described along with their profile of inhibitory activity against 5-lipoxygenase, 12-lipoxygenase, and cyclooxygenase enzymes. The structure--activity relationship suggests that future molecules could be designed to specifically inhibit one or more of these enzymes since there were definite differences in structure--activity relationships for these different enzymes. A representative number of these compounds have been tested in vivo and found to possess potent oral activity in a systemic anaphylaxis model mediated by leukotrienes and topical activity in an arachidonic acid induced inflammation model. One of these molecules, compound 20, demonstrated that a leukotriene antagonist pharmacophore can be modified such that it contains both antagonist activity and 5-lipoxygenase inhibitory activity.

  DOI：

  10.1021/jm00128a027

文献信息

• HUANG, FU-CHIH;SHOUPE, T. SCOTT;LIN, CLARA J.;LEE, THOMAS D. Y.;CHAN, WAN+, J. MED. CHEM., 32,(1989) N, C. 1836-1842
  作者：HUANG, FU-CHIH、SHOUPE, T. SCOTT、LIN, CLARA J.、LEE, THOMAS D. Y.、CHAN, WAN+

  DOI：——

  日期：——
• Differential effects of a series of hydroxamic acid derivatives on 5-lipoxygenase and cyclooxygenase from neutrophils and 12-lipoxygenase from platelets and their in vivo effects on inflammation and anaphylaxis
  作者：Fu Chih Huang、T. Scott Shoupe、Clara J. Lin、Thomas D. Y. Lee、Wan Kit Chan、Jenny Tan、Melvin Schnapper、John T. Suh、Robert J. Gordon

  DOI：10.1021/jm00128a027

  日期：1989.8

  The synthesis of a series of novel substituted hydroxamates has been described along with their profile of inhibitory activity against 5-lipoxygenase, 12-lipoxygenase, and cyclooxygenase enzymes. The structure--activity relationship suggests that future molecules could be designed to specifically inhibit one or more of these enzymes since there were definite differences in structure--activity relationships for these different enzymes. A representative number of these compounds have been tested in vivo and found to possess potent oral activity in a systemic anaphylaxis model mediated by leukotrienes and topical activity in an arachidonic acid induced inflammation model. One of these molecules, compound 20, demonstrated that a leukotriene antagonist pharmacophore can be modified such that it contains both antagonist activity and 5-lipoxygenase inhibitory activity.