2-氯-1-甲基-4,5-二苯基咪唑 | 76463-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-氯-1-甲基-4,5-二苯基咪唑
• 英文名称: 2-chloro-1-methyl-4,5-diphenylimidazole
• 英文别名: 2-chloro-4,5-diphenyl-1-methylimidazole
• CAS: 76463-86-0
• 化学式: C₁₆H₁₃ClN₂
• 分子量: 268.746
• InChiKey: ISYIPVFAOZZSTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-氯-1-甲基-4,5-二苯基咪唑 在 palladium on activated charcoal 正丁基锂 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -70.0~20.0 ℃ 、344.74 kPa 条件下， 反应 1.5h， 生成 N-cyclohexyl-4,5-diphenyl-1-methylimidazole-2-carboxamide
  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
• 作为产物：
  描述：

  1,3-dihydro-1-methyl-4,5-diphenyl-2H-imidazol-2-one 在 三氯氧磷 作用下， 反应 16.0h， 生成 2-氯-1-甲基-4,5-二苯基咪唑
  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

• Substituted imidazoles as cannabinoid receptor modulators
  申请人：——

  公开号：US20030114495A1

  公开（公告）日：2003-06-19

  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.

  本发明涉及将这些新型化合物用于选择性拮抗Cannabinoid-1（CB1）受体。因此，本发明的化合物可用作治疗精神病、记忆障碍、认知障碍、偏头痛、神经病、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的精神药物。这些化合物还可用于治疗物质滥用障碍，特别是阿片类药物、酒精和尼古丁。这些化合物还可用于治疗与过度食物摄入及相关并发症相关的肥胖或进食障碍。同时还声明了结构式（I）的新型化合物。
• On the Reactivity of Halo-1,3-azoles and Related Compounds toward Aromatic SN2 Substitution
  作者：Hiroshi Yamanaka、Setsuya Ohba、Takao Sakamoto

  DOI：10.3987/com-90-5378

  日期：——
• Whittle, Chrostopher P., Australian Journal of Chemistry, 1980, vol. 33, # 8, p. 1545 - 1551
  作者：Whittle, Chrostopher P.

  DOI：——

  日期：——
• WHITTLE C. P., AUSTRAL. J. CHEM., 1980, 33, NO 7, 1545-1551
  作者：WHITTLE C. P.

  DOI：——

  日期：——
• US7057051B2
  申请人：——

  公开号：US7057051B2

  公开（公告）日：2006-06-06