5-bromo-2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid | 527385-04-2

• 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-bromo-2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid
• 英文别名: 5-bromo-2-(2-chlorophenyl)-1-(4-chlorophenyl)imidazole-4-carboxylic acid
• CAS: 527385-04-2
• 化学式: C₁₆H₉BrCl₂N₂O₂
• 分子量: 412.07
• InChiKey: QQGXFOXHUMOPCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid 、 (1S,2S)-反式-1,3-氨基环己醇盐酸盐 在 fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 5-bromo-2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-[(1S,2S)-2-hydroxycyclohexyl]-1H-imidazole-4-carboxamide
  参考文献：
  名称：

  Optimization of imidazole amide derivatives as cannabinoid-1 receptor antagonists for the treatment of obesity

  摘要：

  Several imidazole-based cyclohexyl amides were identified as potent CB-1 antagonists, but they exhibited poor oral exposure in rodents. Incorporation of a hydroxyl moiety on the cyclohexyl ring provided a dramatic improvement in oral exposure, together with a ca. 10-fold decrease in potency. Further optimization provided the imidazole 2-hydroxy-cyclohexyl amide 45, which exhibited hCB-1 K-i = 3.7 nM and caused significant appetite suppression and robust, dose-dependent reduction of body weight gain in industry-standard rat models. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.011
• 作为产物：
  描述：

  2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 72.0h， 以50%的产率得到5-bromo-2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid
  参考文献：
  名称：

  [EN] PREPARATION OF IMIDAZOLE DERIVATIVES AND METHODS OF USE
  [FR] PREPARATION DE DERIVES IMIDAZOLES ET LEURS PROCEDES D'UTILISATION

  摘要：

  公开号：

  WO2005099705A3

文献信息

• [EN] BICYCLIC IMIDAZOLYL PYRIMIDIN-4-ONE CANNABINOID RECEPTOR LIGANDS AND USES THEREOF<br/>[FR] COMPOSES BICYCLIQUES D'IMIDAZOLYLE PYRIMIDIN-4-ONE EN TANT QUE LIGANDS DES RECEPTEURS CANNABINOIDES ET LEURS UTILISATIONS
  申请人：PFIZER PROD INC

  公开号：WO2005061505A1

  公开（公告）日：2005-07-07

  Compounds of Formula (I) are described herein. The compounds have been shown to act as cannabinoid receptor ligands and are therefore useful in the treatment of diseases linked to the mediation of the cannabinoid receptors in animals.

  本文描述了化学式（I）的化合物。这些化合物已被证明能够作为大麻素受体配体，并因此在治疗与动物体内大麻素受体介导相关的疾病方面具有用途。
• [EN] IMIDAZOLE-4-CARBOXAMIDE DERIVATIVES, PREPARATION AND USE THEREOF FOR TREATMENT OF OBESITY<br/>[FR] PREPARATION ET UTILISATION DE DERIVES D'IMIDAZOLE DANS LE TRAITEMENT DE L'OBESITE
  申请人：BAYER PHARMACEUTICALS CORPORAT

  公开号：WO2003040107A1

  公开（公告）日：2003-05-15

  This invention relates to substituted imidazole derivatives of formula I, which have been found to suppress appetite and induce weight loss. The invention also provides methods for synthesis of the compounds, pharmaceutical compositions comprising the compounds, and methods of using such compositions for inducing weight loss and treating obesity and obesity-related disorders.

  本发明涉及公式I的取代咪唑衍生物，已发现其抑制食欲和诱导减重的作用。本发明还提供了合成该化合物的方法、包含该化合物的药物组合物，以及使用这些组合物诱导减重和治疗肥胖和肥胖相关疾病的方法。
• Preparation and use of imidazole derivatives for treatment of obesity
  申请人：Smith A. Roger

  公开号：US20050256167A1

  公开（公告）日：2005-11-17

  This invention relates to substituted imidazole derivatives which have been found to suppress appetite and induce weight loss. The invention also provides methods for synthesis of the compounds, pharmaceutical compositions comprising the compounds, and methods of using such compositions for inducing weight loss and treating obesity and obesity-related disorders.

  本发明涉及取代咪唑衍生物，发现其能够抑制食欲并引起减重。本发明还提供了合成该化合物的方法，包括该化合物的药物组合物，以及使用这样的组合物诱导减重和治疗肥胖和肥胖相关疾病的方法。
• IMIDAZOLE-4-CARBOXAMIDE DERIVATIVES, PREPARATION AND USE THEREOF FOR TREATMENT OF OBESITY
  申请人：Bayer Pharmaceuticals Corporation

  公开号：EP1432691A1

  公开（公告）日：2004-06-30
• US6960601B2
  申请人：——

  公开号：US6960601B2

  公开（公告）日：2005-11-01