Methyl 2-chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinate | 611219-29-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Methyl 2-chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinate
• 英文别名: methyl 2-chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyridine-3-carboxylate
• CAS: 611219-29-5
• 化学式: C₁₉H₁₁Cl₄NO₂
• 分子量: 427.114
• InChiKey: YVSPILKMRVHOIO-UHFFFAOYSA-N

物化性质

• 沸点：
  493.7±45.0 °C(Predicted)
• 密度：
  1.428±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinate 在 钯 氢气 、 desired product 、 phenyl 、 silica gel 、 乙酸乙酯 、 hexanes 、 title compound 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 0.75h， 以to give pure methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylate的产率得到Methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylate
  参考文献：
  名称：

  Substituted 2,3-diphenyl pyridines

  摘要：

  结构式（I）的新化合物是大麻素-1（CB1）受体的拮抗剂和/或反向激动剂，可用于治疗、预防和抑制由CB1受体介导的疾病。本发明的化合物可用作中枢作用药物，用于治疗精神病、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格林-巴利综合征，以及病毒性脑炎、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、运动障碍和精神分裂症。这些化合物还可用于治疗物质滥用障碍、肥胖症或进食障碍以及哮喘、便秘、慢性肠假性梗阻和肝硬化。

  公开号：

  US20050182103A1
• 作为产物：
  描述：

  6-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid 在 盐酸 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl 2-chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinate
  参考文献：
  名称：

  Synthesis and SAR of 5,6-diarylpyridines as human CB1 inverse agonists

  摘要：

  Structure-activity relationship studies for two series of 2-benzyloxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyridines having either a 3-cyano or 3-carboxamide moiety resulted in the preparation of the 2-(3,4-difluorobenzyloxy)-3-nitrile analog 10d and the 2-(3,4-difluorobenzyloxy)-3-(N-propylcarboxamide) analog 16c, (hCB] IC50 = 1.3 and 1.7 nM, respectively) as potent and selective hCB1 inverse agonists. Their synthesis and biological activities are described herein. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.031

文献信息

• Lead optimization of 5,6-diarylpyridines as CB1 receptor inverse agonists
  作者：Christina B. Madsen-Duggan、John S. Debenham、Thomas F. Walsh、Richard B. Toupence、Song X. Huang、Junying Wang、Xinchun Tong、Julie Lao、Tung M. Fong、Marie-Therese Schaeffer、Jing Chen Xiao、Cathy R.-R.C. Huang、Chun-Pyn Shen、D. Sloan Stribling、Lauren P. Shearman、Alison M. Strack、D. Euan MacIntyre、Lex H.T. Van der Ploeg、Mark T. Goulet

  DOI：10.1016/j.bmcl.2007.01.005

  日期：2007.4

  Optimization of the biological activity for 5,6-diarylpyridines as CB1 receptor inverse agonists is described. Food intake and pharmacokinetic evaluation of 3f and 15c indicate that these compounds are effective orally active modulators of CB1. (c) 2007 Elsevier Ltd. All rights reserved.
• SUBSTITUTED 2,3-DIPHENYL PYRIDINES
  申请人：Merck & Co., Inc.

  公开号：EP1492784A2

  公开（公告）日：2005-01-05
• US7271266B2
  申请人：——

  公开号：US7271266B2

  公开（公告）日：2007-09-18
• [EN] SUBSTITUTED 2,3-DIPHENYL PYRIDINES<br/>[FR] 2,3-DIPHENYL-PYRIDINES SUBSTITUEES
  申请人：MERCK & CO INC

  公开号：WO2003082191A2

  公开（公告）日：2003-10-09

  Novel compounds of the structural formula (I) are antagonists and/or inverse agonists of the Cannabinoid-1 (CB1) receptor and are useful in the treatment, prevention and suppression of diseases mediated by the CB1 receptor. The compounds of the present invention are useful as centrally acting 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, movement disorders, and schizophrenia. The compounds are also useful for the treatment of substance abuse disorders, the treatment of obesity or eating disorders, as well as the treatment of asthma, constipation, chronic intestinal pseudo-obstruction, and cirrhosis of the liver.