benzyl 4,5-di-(4-methylphenyl)-1-methylimidazole-2-carboxylate | 489446-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: benzyl 4,5-di-(4-methylphenyl)-1-methylimidazole-2-carboxylate
• 英文别名: benzyl 1-methyl-4,5-bis(4-methylphenyl)imidazole-2-carboxylate
• CAS: 489446-64-2
• 化学式: C₂₆H₂₄N₂O₂
• 分子量: 396.489
• InChiKey: SIEQHBLPHYILHG-UHFFFAOYSA-N

物化性质

• 沸点：
  562.3±60.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  benzyl 4,5-di-(4-methylphenyl)-1-methylimidazole-2-carboxylate 在 钯 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4,5-di-(4-methylphenyl)-1-methylimidazole-2-carboxylic acid
  参考文献：
  名称：

  Substituted imidazoles as cannabinoid receptor modulators

  摘要：

  本发明涉及使用本发明的化合物作为大麻素-1（CB1）受体的拮抗剂和/或反向激动剂，特别是用于治疗、预防和抑制由大麻素-1（CB1）受体介导的疾病。本发明涉及使用这些新型化合物选择性拮抗大麻素-1（CB1）受体。因此，本发明的化合物在治疗精神病、记忆障碍、认知障碍、偏头痛、神经病理、神经炎症性疾病（包括多发性硬化症和吉兰-巴雷综合征）、病毒性脑炎、脑血管意外和头部创伤的炎症后遗症、焦虑症、压力、癫痫、帕金森病和精神分裂症方面是有用的。这些化合物还可用于治疗物质滥用障碍，特别是对阿片类、酒精和尼古丁的治疗。这些化合物还可用于治疗与过度食物摄入和相关并发症相关的肥胖症或进食障碍。本发明还声明了结构式（I）的新型化合物。

  公开号：

  US20060089356A1
• 作为产物：
  描述：

  4,4-二甲基苯甲酸 在 正丁基锂 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙二醇 为溶剂， 反应 19.0h， 生成 benzyl 4,5-di-(4-methylphenyl)-1-methylimidazole-2-carboxylate
  参考文献：
  名称：

  Synthesis and activity of 4,5-diarylimidazoles as human CB1 receptor inverse agonists

  摘要：

  Structure-activity relationship studies directed toward the optimization of 4,5-diarylimidazole-2-carboxamide analogs as human CBI receptor inverse agonists resulted in the discovery of the two amide derivatives 24a and b (hCB1 IC50 = 6.1 and 4.0 nM) which also demonstrated efficacy in overnight feeding studies in the rat for reduction in both food intake and overall body weight. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.078

文献信息

• Method of treatment or prevention of obesity
  申请人：Fong M Tung

  公开号：US20050171161A1

  公开（公告）日：2005-08-04

  The present invention relates to a method of treating or preventing obesity (or suppressing the appetite) in a human patient by antagonizing CB1 receptors and inhibiting the enzyme 11β-HSD1 in an amount that is effective to treat or prevent obesity. Compounds useful in the present invention have an ion channel activity level greater than about 2 μM. Preferably the compound is a dual selective inhibitor, selectively antagonizing CB1 receptors and selectively inhibiting the enzyme 11β-HSD1

  本发明涉及一种通过拮抗CB1受体和抑制11β-HSD1酶以有效治疗或预防肥胖（或抑制食欲）的方法。本发明中有用的化合物具有大于约2μM的离子通道活性水平。最好的化合物是双重选择性抑制剂，可以选择性地拮抗CB1受体和选择性地抑制酶11β-HSD1。
• US7057051B2
  申请人：——

  公开号：US7057051B2

  公开（公告）日：2006-06-06
• US7572785B2
  申请人：——

  公开号：US7572785B2

  公开（公告）日：2009-08-11
• [EN] SUBSTITUTED IMIDAZOLES AS CANNABINOID RECEPTOR MODULATORS<br/>[FR] IMIDAZOLES SUBSTITUES SERVANT DE MODULATEURS DE RECEPTEURS DE CANNABINOIDES
  申请人：MERCK & CO INC

  公开号：WO2003007887A2

  公开（公告）日：2003-01-30

  The use of compounds of the present invention as antagonists and/or inverse agonists of the Cannabinoid-1 (CB1)receptor particularly in the treatment, prevention and suppression of diseases mediated by the Cannabinoid-1 (CB1) receptor. The invention is concerned with the use of these novel compounds to selectively antagonize the Cannabinoid-1 (CB1) receptor. As such, compounds of the present invention are useful as psychotropic drugs in the treatment of psychosis, memory deficits, cognitive disorders, migraine, neuropathy, neuro-inflammatory disorders including multiple sclerosis and Guillain-Barre syndrome and the inflammatory sequelae of viral encephalitis, cerebral vascular accidents, and head trauma, anxiety disorders, stress, epilepsy, Parkinson s disease, and schizophrenia. The compounds are also useful for the treatment of substance abuse disorders, particularly to opiates, alcohol, and nicotine. The compounds are also useful for the treatment of obesity or eating disorders associated with excessive food intake and complications associated therewith. Novel compounds of structural formula (I) are also claimed.