methyl (3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)methylcarbamate | 1016552-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl (3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)methylcarbamate
• 英文别名: methyl N-[[3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)pyrazol-4-yl]methyl]carbamate
• CAS: 1016552-31-0
• 化学式: C₂₄H₂₂Cl₃N₅O₃
• 分子量: 534.829
• InChiKey: VUPSSAFXLGGMSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3-(5-叔丁基-1,3,4-恶二唑-2-基)-5-(4-氯苯基)-1-(2,4-二氯苯基)-1H-吡唑-4-基)甲醇 、 伯吉斯试剂 以 四氢呋喃 为溶剂， 反应 1.0h， 以45 mg的产率得到methyl (3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)methylcarbamate
  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