5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-n,4-dimethyl-1H-pyrazole-3-carboxamide | 1159835-90-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-n,4-dimethyl-1H-pyrazole-3-carboxamide
• 英文别名: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N,4-dimethylpyrazole-3-carboxamide
• CAS: 1159835-90-1
• 化学式: C₁₈H₁₄Cl₃N₃O
• 分子量: 394.688
• InChiKey: OOQZEQQIRIYMRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-n,4-dimethyl-1H-pyrazole-3-carboxamide 在 五氯化磷 、 迭氮酸 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成 C₁₈H₁₃Cl₃N₆
  参考文献：
  名称：

  Tetrazole-biarylpyrazole derivatives as cannabinoid CB1 receptor antagonists

  摘要：

  Cannabinoid CB1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and related metabolic disorders were reported in 2001. To further evaluate the properties of CB receptors, we have designed a new series of tetrazole-biarylpyrazoles. The various analogues were efficiently prepared and bioassayed for binding to cannabinoid CB1 receptor. Six of the new compounds which displayed high in vitro CB1 binding affinities were assayed for binding to CB2 receptor. Noticeably, cyclopentyl-tetrazole (9a) demonstrated good binding affinity and selectivity for CB1 receptor (IC50 = 11.6 nM and CB2/CB1 = 366). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.061
• 作为产物：
  描述：

  5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride 、 甲胺 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-n,4-dimethyl-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  Tetrazole-biarylpyrazole derivatives as cannabinoid CB1 receptor antagonists

  摘要：

  Cannabinoid CB1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and related metabolic disorders were reported in 2001. To further evaluate the properties of CB receptors, we have designed a new series of tetrazole-biarylpyrazoles. The various analogues were efficiently prepared and bioassayed for binding to cannabinoid CB1 receptor. Six of the new compounds which displayed high in vitro CB1 binding affinities were assayed for binding to CB2 receptor. Noticeably, cyclopentyl-tetrazole (9a) demonstrated good binding affinity and selectivity for CB1 receptor (IC50 = 11.6 nM and CB2/CB1 = 366). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.061

文献信息

• [EN] PYRAZOLE DERIVATIVES AS CANNABINOID RECEPTOR 1 ANTAGONISTS<br/>[FR] DÉRIVÉS DE PYRAZOLE UTILISÉS EN TANT QU'ANTAGONISTES DU RÉCEPTEUR DE TYPE 1 DES CANNABINOÏDES
  申请人：RES TRIANGLE INST

  公开号：WO2012174362A1

  公开（公告）日：2012-12-20

  The invention provides compounds capable of acting as antagonists at cannabanoid receptors according to the following formula: Such compounds may be used to treat conditions for which the cannabinoid receptor system has been implicated, such as obesity, liver disease, diabetes, pain, and inflammation.

  该发明提供了一种能够作为大麻素受体拮抗剂的化合物，其化学式如下：这些化合物可用于治疗与大麻素受体系统有关的疾病，如肥胖、肝病、糖尿病、疼痛和炎症。
• PYRAZOLE DERIVATIVES AS CANNABINOID RECEPTOR 1 ANTAGONISTS
  申请人：Fulp Alan Bradley

  公开号：US20140107157A1

  公开（公告）日：2014-04-17

  The invention provides compounds capable of acting as antagonists at cannabanoid receptors according to the following formula: Such compounds may be used to treat conditions for which the cannabinoid receptor system has been implicated, such as obesity, liver disease, diabetes, pain, and inflammation.

  本发明提供了一种能够作为大麻素受体拮抗剂的化合物，其化学式如下：这些化合物可用于治疗与大麻素受体系统有关的疾病，如肥胖症、肝脏疾病、糖尿病、疼痛和炎症等。
• Synthesis and structure–activity relationship of novel diarylpyrazole imide analogues as CB1 cannabinoid receptor ligands
  作者：Kwang-Seop Song、Min Ju Kim、Hee Jeong Seo、Sung-Han Lee、Myung Eun Jung、Soo-Un Kim、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmc.2009.03.006

  日期：2009.4

  A myriad of research groups have been engaged in searching for novel CB1 receptor antagonists, since SR141716A (rimonabant), a CB1 receptor antagonist, was discovered for an obesity treatment. In this research, extended series, based on the 1,5-diarylpyrazole template of rimonabant, was synthesized and tested for CB1 receptor binding affinity. In the present study, N-piperidinylcarboxamide group of rimonabant was replaced with the corresponding sulfonamide, imide, N-methylimide and methylenediamide, respectively. The SAR studies to optimize the CB1 binding affinity led to the potent imide derivatives. The in vivo efficacy test of a derivative (16f) gave a promising result for this novel scaffold. In order to explore physicochemical properties (hydrophobic, steric and electronic) of the representative imide derivatives responsible for their CB1 receptor binding affinity, quantitative structure activity relationship (QSAR) studies were performed. Hansch QSAR models, which were moderate in the explanation for SAR, were generated with hydrophobic, steric and electronic properties of substituents. Especially, the Taft Es-based parabolic model was obtained with the best correlation result (r(2) = 0.846). (C) 2009 Elsevier Ltd. All rights reserved.
• CANNABINOID RECEPTOR ANTAGONISTS/INVERSE AGONISTS USEFUL FOR TREATING OBESITY
  申请人：McElroy John Francis

  公开号：US20100144791A1

  公开（公告）日：2010-06-10

  The present invention provides novel pyrazoles that are useful as cannabinoid receptor antagonists and pharmaceutical compositions thereof and methods of using the same for treating obesity, diabetes, and/or cardiometabolic disorders.
• US8088798B2
  申请人：——

  公开号：US8088798B2

  公开（公告）日：2012-01-03