4-(5-phenyl-1H-3-pyrazolyl)butanoic acid | 268726-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-phenyl-1H-3-pyrazolyl)butanoic acid
• 英文别名: 4-(3-phenyl-1H-pyrazol-5-yl)butanoic acid
• CAS: 268726-70-1
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: ZAUYTJFFMOZMOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-phenyl-1H-3-pyrazolyl)butanoic acid 在 氯化亚砜 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 N1,N1-dimethyl-4-(5-phenyl-1H-3-pyrazolyl)butanamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Pyrazoles and Indazoles as Activators of the Nitric Oxide Receptor, Soluble Guanylate Cyclase

  摘要：

  Database searching and compound screening identified 1-benzyl-3-(3-dimethylaminopropyloxy)-indazole (benzydamine, 3) as a potent activator of the nitric oxide receptor, soluble guanylate cyclase. A comprehensive structure-activity relationship study surrounding 3 clearly showed that the indazole C-3 dimethylaminopropyloxy substituent was critical for enzyme activity. However replacement of the indazole ring of 3 by appropriately substituted pyrazoles maintained enzyme activity. Compounds were evaluated for inhibition of platelet aggregation and showed a general lipophilicity requirement. Aryl-substituted pyrazoles 32, 34, and 43 demonstrated potent activation of soluble guanylate cyclase and potent inhibition of platelet aggregation. Pharmacokinetic studies in rats showed that compound 32 exhibits modest oral bioavailability (12%). Furthermore 32 has an excellent selectivity profile notably showing no significant inhibition of phosphodiesterases or nitric oxide synthases.

  DOI：

  10.1021/jm001034k
• 作为产物：
  描述：

  7-phenyl-5,7-diketoheptanoic acid 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-(5-phenyl-1H-3-pyrazolyl)butanoic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Pyrazoles and Indazoles as Activators of the Nitric Oxide Receptor, Soluble Guanylate Cyclase

  摘要：

  Database searching and compound screening identified 1-benzyl-3-(3-dimethylaminopropyloxy)-indazole (benzydamine, 3) as a potent activator of the nitric oxide receptor, soluble guanylate cyclase. A comprehensive structure-activity relationship study surrounding 3 clearly showed that the indazole C-3 dimethylaminopropyloxy substituent was critical for enzyme activity. However replacement of the indazole ring of 3 by appropriately substituted pyrazoles maintained enzyme activity. Compounds were evaluated for inhibition of platelet aggregation and showed a general lipophilicity requirement. Aryl-substituted pyrazoles 32, 34, and 43 demonstrated potent activation of soluble guanylate cyclase and potent inhibition of platelet aggregation. Pharmacokinetic studies in rats showed that compound 32 exhibits modest oral bioavailability (12%). Furthermore 32 has an excellent selectivity profile notably showing no significant inhibition of phosphodiesterases or nitric oxide synthases.

  DOI：

  10.1021/jm001034k