2-(1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-1H-imidazol-4-yl)-5-t-butyl-1,3,4-thiadiazole | 1049683-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-1H-imidazol-4-yl)-5-t-butyl-1,3,4-thiadiazole
• 英文别名: GCC1878A；2-(1-(4-Bromophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-1H-imidazol-4-yl)-5-tert-butyl-1,3,4-thiadiazole；2-[1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-ethylimidazol-4-yl]-5-tert-butyl-1,3,4-thiadiazole
• CAS: 1049683-44-4
• 化学式: C₂₃H₂₁BrCl₂N₄S
• 分子量: 536.323
• InChiKey: IKCRNKVIIZFXLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-N'-pivaloyl-1H-imidazole-4-carbohydrazide 在 劳森试剂 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以64%的产率得到2-(1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-1H-imidazol-4-yl)-5-t-butyl-1,3,4-thiadiazole
  参考文献：
  名称：

  Diarylimidazolyl oxadiazole and thiadiazole derivatives as cannabinoid CB1 receptor antagonists

  摘要：

  Since the CB1 receptor antagonist SR141716 (rimonabant) was reported to modulate food intake, CB1 antagonism has been considered as a new therapeutic target in the treatment of obesity. Several series of derivatives based on diarylimidazolyl oxadiazole and thiadiazole scaffolds were synthesized and tested for CB1 receptor binding affinity. SAR studies directed toward the optimization of imidazole scaffolds resulted in the discovery of 10s which showed highest potency for CB1 receptor binding affinity (IC50 = 1.91 nM) prepared to date. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.130

文献信息

• HETEROARYL-IMIDAZOLE DERIVATIVES AS CANNABINOID CB1 RECEPTOR ANTAGONISTS
  申请人：Lee Jinhwa

  公开号：US20080207704A1

  公开（公告）日：2008-08-28

  A heteroaryl-imidazole compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB 1 receptor inverse agonist or antagonist, which is useful for preventing or treating obesity and obesity-related metabolic disorders. The present invention also provides a method for preparing a heteroaryl-imidazole compound of formula (I), a pharmaceutical composition containing a heteroaryl-imidazole compound of formula (I), and a method for preventing or treating obesity and obesity-related metabolic disorders.

  一种具有化学式(I)的杂环芳基咪唑化合物或其药学上可接受的盐作为一种大麻素CB1受体的反向激动剂或拮抗剂，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具有化学式(I)的杂环芳基咪唑化合物的方法，含有具有化学式(I)的杂环芳基咪唑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。
• Heteroaryl-Imidazole Derivatives as Cannabinoid CB1 Receptor Antagonists
  申请人：LEE Jinhwa

  公开号：US20080207705A1

  公开（公告）日：2008-08-28

  A novel heteroaryl-imidazole compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB 1 receptor inverse agonist or antagonist, which is useful for preventing or treating obesity and obesity-related metabolic disorders. The present invention also provides a method for preparing same, a pharmaceutical composition containing same, and a method for preventing or treating obesity and obesity-related metabolic disorders.

  一种新型杂环取代咪唑化合物（I）或其药学上可接受的盐，作为大麻素CB1受体的反向激动剂或拮抗剂具有良好的效果，可用于预防或治疗肥胖和肥胖相关的代谢性疾病。本发明还提供了一种制备该化合物的方法，一种含有该化合物的制药组合物以及一种预防或治疗肥胖和肥胖相关代谢性疾病的方法。
• [EN] HETEROARYL-IMIDAZOLE DERIVATIVES AS CANNABINOID CB1 RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS D'HÉTÉROARYLE-IMIDAZOLE EN TANT QU'ANTAGONISTES DE RÉCEPTEUR DE CANNABINOÏDE CB1
  申请人：GREEN CROSS CORP

  公开号：WO2008105607A1

  公开（公告）日：2008-09-04

  [EN] A novel heteroaryl-imidazole compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB1 receptor inverse agonist or antagonist, which is useful for preventing or treating obesity and obesity-related metabolic disorders. The present invention also provides a method for preparing same, a pharmaceutical composition containing same, and a method for preventing or treating obesity and obesity-related metabolic disorders.
  [FR] L'invention concerne un nouveau composé d'hétéroaryle-imidazole de la formule (I), ou un sel acceptable du point de vue pharmaceutique de celui-ci, qui est efficace en tant qu'agoniste inverse ou antagoniste de récepteur de cannabinoïde CB1, qui s'utilise pour empêcher ou traiter l'obésité et des troubles métaboliques en rapport avec l'obésité. La présente invention propose également un procédé pour sa préparation, une composition pharmaceutique le contenant, et un procédé pour empêcher ou traiter l'obésité et des troubles métaboliques en rapport avec l'obésité.
• Diarylimidazolyl oxadiazole and thiadiazole derivatives as cannabinoid CB1 receptor antagonists
  作者：Jong Yup Kim、Hee Jeong Seo、Sung-Han Lee、Myung Eun Jung、Kwangwoo Ahn、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmcl.2008.10.130

  日期：2009.1

  Since the CB1 receptor antagonist SR141716 (rimonabant) was reported to modulate food intake, CB1 antagonism has been considered as a new therapeutic target in the treatment of obesity. Several series of derivatives based on diarylimidazolyl oxadiazole and thiadiazole scaffolds were synthesized and tested for CB1 receptor binding affinity. SAR studies directed toward the optimization of imidazole scaffolds resulted in the discovery of 10s which showed highest potency for CB1 receptor binding affinity (IC50 = 1.91 nM) prepared to date. (C) 2008 Elsevier Ltd. All rights reserved.