5-bromo-1-(4-chloro-phenyl)-2-(2-chloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester | 784181-24-4

• 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-1-(4-chloro-phenyl)-2-(2-chloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 5-bromo-2-(2-chlorophenyl)-1-(4-chlorophenyl)imidazole-4-carboxylate
• CAS: 784181-24-4
• 化学式: C₁₈H₁₃BrCl₂N₂O₂
• 分子量: 440.123
• InChiKey: CZKWLZDXSYXZRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-1-(4-chloro-phenyl)-2-(2-chloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 5-bromo-2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid
  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：

  在 溶剂黄146 作用下， 生成 5-bromo-1-(4-chloro-phenyl)-2-(2-chloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester
  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

文献信息

• Cannabinoid receptor ligands and uses thereof
  申请人：Pfizer Inc

  公开号：US20040248881A1

  公开（公告）日：2004-12-09

  Compounds of Formula (I) or (II) that act as cannabinoid receptor ligands and their uses in the treatment of diseases linked to the mediation of the cannabinoid receptors in animals are described herein. 1

  化合物的化学式（I）或（II），其作为大麻素受体配体并在治疗与动物体内大麻素受体介导相关疾病中的用途被描述在此。
• [EN] BICYCLIC PYRIDAZINONE CANNABINOID RECEPTOR LIGANDS AND USES THEREOF<br/>[FR] COMPOSES BICYCLIQUES DE PYRIDAZINONE UTILES EN TANT QUE LIGANDS DES RECEPTEURS CANNABINOIDES ET LEURS UTILISATIONS
  申请人：PFIZER PROD INC

  公开号：WO2005061504A1

  公开（公告）日：2005-07-07

  Compounds of Formula (I) and (II) are described herein, as well as their uses in the treatment of diseases linked to the mediation of the cannabinoid receptors (in particular, the CB-1 receptor) in animals.

  本文描述了式(I)和(II)的化合物，以及它们在治疗与动物体内大麻素受体介导有关的疾病中的用途（特别是CB-1受体）。
• [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 COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSES D'IMIDAZOLE ET LEURS UTILISATIONS
  申请人：PFIZER PROD INC

  公开号：WO2005009974A1

  公开（公告）日：2005-02-03

  Compounds of Formula (I) that act as cannabinoid receptor ligands and their uses in the treatment of diseases linked to the activation of the cannabinoid receptors in animals are described herein.

  本文描述了作为大麻素受体配体的化合物(I)及其在治疗与动物大麻素受体激活相关的疾病中的用途。
• Imidazole compounds and uses thereof
  申请人：Carpino A. Philip

  公开号：US20050026983A1

  公开（公告）日：2005-02-03

  Compounds of Formula (I) that act as cannabinoid receptor ligands and their uses in the treatment of diseases linked to the activation of the cannabinoid receptors in animals are described herein.

  本文描述了作为大麻素受体配体的化合物(I)以及它们在治疗与动物中大麻素受体激活有关的疾病中的用途。