N'-acetyl-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbohydrazide | 1161827-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N'-acetyl-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbohydrazide
• 英文别名: N'-acetyl-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)pyrazole-4-carbohydrazide
• CAS: 1161827-21-9
• 化学式: C₂₄H₂₁Cl₃N₆O₃
• 分子量: 547.828
• InChiKey: WCLWJGAPQPVVCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N'-acetyl-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbohydrazide 在 伯吉斯试剂 作用下， 以 四氢呋喃 为溶剂， 生成 2-tert-butyl-5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrazol-3-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Pentacycle derivatives 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 pentacycle derivatives. Five of the new compounds which displayed high in vitro rCB1 binding affinities were assayed for binding to hCB2 receptor. Noticeably, 2-(5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(5-methyl- 1,3,4-thiadiazol-2-yl)-1H-pyrazol-3-yl)-5-(1-(trifluoromethyl) cyclopropyl)-1,3,4-oxadiazole (16l) demonstrated good binding affinity and decent selectivity for rCB1 receptor (IC50 = 1.72 nM, hCB2/rCB1 = 142). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.015
• 作为产物：
  描述：

  3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxylic acid 、 乙酰肼 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N'-acetyl-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbohydrazide
  参考文献：
  名称：

  Pentacycle derivatives 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 pentacycle derivatives. Five of the new compounds which displayed high in vitro rCB1 binding affinities were assayed for binding to hCB2 receptor. Noticeably, 2-(5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(5-methyl- 1,3,4-thiadiazol-2-yl)-1H-pyrazol-3-yl)-5-(1-(trifluoromethyl) cyclopropyl)-1,3,4-oxadiazole (16l) demonstrated good binding affinity and decent selectivity for rCB1 receptor (IC50 = 1.72 nM, hCB2/rCB1 = 142). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.015

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。
• Pentacycle derivatives as cannabinoid CB1 receptor ligands
  作者：Suk Ho Lee、Hee Jeong Seo、Min Ju Kim、Suk Youn Kang、Sung-Han Lee、Kwangwoo Ahn、MinWoo Lee、Ho-Kyun Han、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmcl.2009.10.015

  日期：2009.12

  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 pentacycle derivatives. Five of the new compounds which displayed high in vitro rCB1 binding affinities were assayed for binding to hCB2 receptor. Noticeably, 2-(5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(5-methyl- 1,3,4-thiadiazol-2-yl)-1H-pyrazol-3-yl)-5-(1-(trifluoromethyl) cyclopropyl)-1,3,4-oxadiazole (16l) demonstrated good binding affinity and decent selectivity for rCB1 receptor (IC50 = 1.72 nM, hCB2/rCB1 = 142). (C) 2009 Elsevier Ltd. All rights reserved.