5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-2-carboxylic acid | 875667-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-2-carboxylic acid
• 英文别名: 5-(4-Chlorophenyl)-4-(2,4-dichlorophenyl)-1-methylpyrrole-2-carboxylic acid
• CAS: 875667-63-3
• 化学式: C₁₈H₁₂Cl₃NO₂
• 分子量: 380.658
• InChiKey: OMEQVDHJSSQZEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-2-carboxylic acid 在 N,N'-羰基二咪唑 、 氨 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 乙醚 为溶剂， 反应 2.0h， 生成 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  DERIVATIVES OF 4,5-DIARYLPYRROLE, PREPARATION METHOD THEREOF AND USE OF SAME IN THERAPEUTICS

  摘要：

  该发明涉及具有如下式（I）的化合物：其中X，R1，R2，R3，R4和R5如本文所定义。该发明还涉及其制备方法以及在治疗中的使用。

  公开号：

  US20080176924A1
• 作为产物：
  描述：

  5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester 在 氢氧化钾 、 18-冠醚-6 作用下， 以 乙二醇 为溶剂， 反应 6.0h， 生成 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Regioselective Synthesis of Highly Aryl‐Substituted Pyrrole Carboxylates as Useful Medicinal Chemistry Leads

  摘要：

  The regioselective syntheses of two pharmaceutically relevant pyrrole scaffolds are described. A synthetic route for the preparation of differentially substituted pyrrole-3,4-dicarboxylates is presented and exemplified. This route circumvents some of the problems and limitations associated with previous butynedioic diester condensations and 1,3-dipolar cycloaddition reactions. A route to the related 4,5-diarylpyrrole2-carboxylic acid scaffold is also presented. Both routes allow for the regiocontrolled preparation of highly substituted pyrrole pharmacophore cores.

  DOI：

  10.1080/00397910701481237

文献信息

• PYRROLE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC USE
  申请人：Barth Francis

  公开号：US20070149596A1

  公开（公告）日：2007-06-28

  The invention concerns compounds of formula (I): Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are as defined herein. The invention also concerns the method for preparing said compounds and their therapeutic use.

  该发明涉及式(I)的化合物：其中R1、R2、R3、R4、R5、R6、R7、R8和R9如本文所定义。该发明还涉及制备所述化合物的方法及其治疗用途。
• Rational design of a novel peripherally-restricted, orally active CB1 cannabinoid antagonist containing a 2,3-diarylpyrrole motif
  作者：Laurent Hortala、Murielle Rinaldi-Carmona、Christian Congy、Laurent Boulu、Freddy Sadoun、Gérard Fabre、Olivier Finance、Francis Barth

  DOI：10.1016/j.bmcl.2010.06.017

  日期：2010.8

  A new series of 2,3-diarylpyrroles have been prepared and evaluated as CB1 antagonists. Modulation of the topological polar surface area allowed the identification of high affinity peripherally-restricted CB1 antagonists. Compound 11, obtained after further optimization of the metabolic profile displayed very low brain penetration, yet was able to reverse CP55940-induced gastrointestinal transit inhibition following oral administration. (C) 2010 Elsevier Ltd. All rights reserved.
• PYRROLE DERIVATIVES, INTERMEDIATES THEREFOR, PREPARATION AND THERAPEUTIC USE THEREOF
  申请人：BARTH Francis

  公开号：US20080194581A1

  公开（公告）日：2008-08-14

  The invention concerns compounds of formula (I): Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are as defined herein. The invention also concerns the method for preparing said compounds including the intermediates therefor and their therapeutic use.
• US7381727B2
  申请人：——

  公开号：US7381727B2

  公开（公告）日：2008-06-03
• US7618995B2
  申请人：——

  公开号：US7618995B2

  公开（公告）日：2009-11-17