2-(4-((2H-tetrazol-2-yl)methyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl)-5-tert-butyl-1,3,4-oxadiazole | 1084763-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-((2H-tetrazol-2-yl)methyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl)-5-tert-butyl-1,3,4-oxadiazole
• 英文别名: 2-tert-butyl-5-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(tetrazol-2-ylmethyl)pyrazol-3-yl]-1,3,4-oxadiazole
• CAS: 1084763-15-4
• 化学式: C₂₃H₁₉Cl₃N₈O
• 分子量: 529.816
• InChiKey: SUTKDEUGJICEFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(4-(bromomethyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl)-5-tert-butyl-1,3,4-oxadiazole 、 2H-tetrazole 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-(4-((2H-tetrazol-2-yl)methyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl)-5-tert-butyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Biarylpyrazolyl Oxadiazole as Potent, Selective, Orally Bioavailable Cannabinoid-1 Receptor Antagonists for the Treatment of Obesity

  摘要：

  Since the CB1 cannabinoid receptor antagonist 1 (SR141716, rimonabant) was previously reported to modulate food intake, CB1 antagonism has been considered as a new therapeutic target for the treatment of obesity. In the present study, biarylpyrazole analogues based on a pyrazole core coupled with 1,3,4-oxadiazole were synthesized and tested for CB1 receptor binding affinity. Thorough SAR studies to optimize pyrazole substituents as well as 1,3,4-oxadiazole ring led to several novel CB1 antagonists with IC50 similar to 1 nM for the CB1 receptor binding. Among these analogues, we identified 2-(4-((1H-1,2,4-triazol-1-yl)methyl)-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl)-5-(1-(trifluoromethyl)cyclopropyl)-1,3,4-oxa- diazole 43c as a promising precandidate for the development as an antiobesity agent.

  DOI：

  10.1021/jm800843r