5-(4-bromophenyl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(2,4-dichlorophenyl)-N-phenyl-1H-pyrazole-4-carboxamide | 1150311-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-bromophenyl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(2,4-dichlorophenyl)-N-phenyl-1H-pyrazole-4-carboxamide
• 英文别名: 5-(4-bromophenyl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(2,4-dichlorophenyl)-N-phenylpyrazole-4-carboxamide
• CAS: 1150311-35-5
• 化学式: C₂₈H₂₂BrCl₂N₅O₂
• 分子量: 611.325
• InChiKey: UVFWCIGTUOMCPO-UHFFFAOYSA-N

物化性质

• 密度：
  1.50±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  、 苯胺 以 四氢呋喃 为溶剂， 生成 5-(4-bromophenyl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(2,4-dichlorophenyl)-N-phenyl-1H-pyrazole-4-carboxamide
  参考文献：
  名称：

  Oxadiazole-diarylpyrazole 4-carboxamides as cannabinoid CB1 receptor ligands

  摘要：

  Cannabinoid CB-1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and obesity-related metabolic disorders were reported in 2001. To further evaluate the properties of CB receptors, we have designed and efficiently prepared a series of oxadiazole-diarylpyrazole 4-carboxamides. Six of the new compounds which displayed high in vitro CB1 binding affinities were assayed for binding to CB2 receptor. Noticeably, 5-(4-bromophenyl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(2,4-dichlorophenyl)-N-phenyl-1H-pyrazole-4-carboxamide (12q) and 5-(4-bromophenyl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(2,4-dichlorophenyl)-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide (12r) demonstrated good binding affinity and decent selectivity for CB1 receptor (IC50 = 1.35 nM, CB2/CB1 = 286 for 12q; IC50 = 1.46 nM, CB2/CB1 = 256 for 12r). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.063

文献信息

• [EN] BIARYLPYRAZOLE 4-CARBOXAMIDES AS CANNABINOID CB1 RECEPTOR LIGANDS<br/>[FR] BIARYLPYRAZOLE-4-CARBOXAMIDES COMME LIGANDS DES RÉCEPTEURS CANNABINOÏDES CB1
  申请人：GREEN CROSS CORP

  公开号：WO2009078498A1

  公开（公告）日：2009-06-25

  A novel biarylpyrazole 4-carboxamide compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB1 receptor ligand, which is useful for preventing or treating obesity and obesity-related metabolic disorders. The present invention also provide a method for preparing same, a pharmaceutical composition containing same, and a method for preventing or treating obesity and obesity-related metabolic disorders.

  一种具有化学式(I)的新型联苯吡唑-4-羧酰胺化合物或其药用盐，作为一种有效的大麻素CB1受体配体，可用于预防或治疗肥胖和与肥胖相关的代谢紊乱。本发明还提供了一种制备该化合物的方法，含有该化合物的药物组合物，以及预防或治疗肥胖和与肥胖相关的代谢紊乱的方法。
• Oxadiazole-diarylpyrazole 4-carboxamides as cannabinoid CB1 receptor ligands
  作者：Suk Ho Lee、Hee Jeong Seo、Min Ju Kim、Suk Youn Kang、Kwang-Seop Song、Sung-Han Lee、Myung Eun Jung、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmcl.2009.02.063

  日期：2009.4

  Cannabinoid CB-1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and obesity-related metabolic disorders were reported in 2001. To further evaluate the properties of CB receptors, we have designed and efficiently prepared a series of oxadiazole-diarylpyrazole 4-carboxamides. Six of the new compounds which displayed high in vitro CB1 binding affinities were assayed for binding to CB2 receptor. Noticeably, 5-(4-bromophenyl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(2,4-dichlorophenyl)-N-phenyl-1H-pyrazole-4-carboxamide (12q) and 5-(4-bromophenyl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-(2,4-dichlorophenyl)-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide (12r) demonstrated good binding affinity and decent selectivity for CB1 receptor (IC50 = 1.35 nM, CB2/CB1 = 286 for 12q; IC50 = 1.46 nM, CB2/CB1 = 256 for 12r). (C) 2009 Elsevier Ltd. All rights reserved.