N-(5-氧代-1-苯基-4H-吡唑-3-基)戊酰胺 | 71683-82-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: N-(5-氧代-1-苯基-4H-吡唑-3-基)戊酰胺
• 英文名称: pentanoic acid N-(5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-amide
• 英文别名: 5-pentanoylamino-2-phenyl-2,4-dihydro-pyrazol-3-one；N-(5-Oxo-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)pentanamide；N-(5-oxo-1-phenyl-4H-pyrazol-3-yl)pentanamide
• CAS: 71683-82-4
• 化学式: C₁₄H₁₇N₃O₂
• 分子量: 259.308
• InChiKey: VPNKQPILYDGSJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氨基-1-苯基-2-吡唑啉-5-酮 、 戊酰氯 以 1,4-二氧六环 为溶剂， 以67%的产率得到N-(5-氧代-1-苯基-4H-吡唑-3-基)戊酰胺
  参考文献：
  名称：

  Synthesis and biological evaluation of a new class of acyl derivatives of 3-amino-1-phenyl-4,5-dihydro-1H-pyrazol-5-one as potential dual cyclooxygenase (COX-1 and COX-2) and human lipoxygenase (5-LOX) inhibitors

  摘要：

  A series of acyl derivatives of 3-amino-1-phenyl-4,5-dihydro-1H-pyrazol-5-one as potential human 5-LOX and COX 1 and COX-2 inhibitors structurally related to the 1-phenyl-3-pyrazolidinone (phenidone, 1) have been synthesized and the activity against COX-1, COX-2 and human 5-LOX enzymes has been evaluated. All the derivatives showed poor activity against enzymes. These data, together with our previous studies, indicated that phenidone and related compounds are not suitable as human 5-LOX inhibitors and that pyrazoline nucleus should not be considered a good scaffold for inhibitors of human 5-LOX enzyme, suggesting the necessity to revisit the proposed mechanism of action of phenidone (1) in human models.

  DOI：

  10.1016/j.farmac.2004.12.009

文献信息

• Synthesis and biological evaluation of a new class of acyl derivatives of 3-amino-1-phenyl-4,5-dihydro-1H-pyrazol-5-one as potential dual cyclooxygenase (COX-1 and COX-2) and human lipoxygenase (5-LOX) inhibitors
  作者：Claudia Cusan、Giampiero Spalluto、Maurizio Prato、Michael Adams、Antje Bodensieck、Rudolf Bauer、Aurelia Tubaro、Paolo Bernardi、Tatiana Da Ros

  DOI：10.1016/j.farmac.2004.12.009

  日期：2005.4

  A series of acyl derivatives of 3-amino-1-phenyl-4,5-dihydro-1H-pyrazol-5-one as potential human 5-LOX and COX 1 and COX-2 inhibitors structurally related to the 1-phenyl-3-pyrazolidinone (phenidone, 1) have been synthesized and the activity against COX-1, COX-2 and human 5-LOX enzymes has been evaluated. All the derivatives showed poor activity against enzymes. These data, together with our previous studies, indicated that phenidone and related compounds are not suitable as human 5-LOX inhibitors and that pyrazoline nucleus should not be considered a good scaffold for inhibitors of human 5-LOX enzyme, suggesting the necessity to revisit the proposed mechanism of action of phenidone (1) in human models.