5-(4-chlorophenyl)-2-methyl-1-(4-sulfamoylphenyl)-1H-3-carboxylic acid

• 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)-2-methyl-1-(4-sulfamoylphenyl)-1H-3-carboxylic acid
• 英文别名: 5-(4-chloro-phenyl)-2-methyl-1-(4-sulfamoyl-phenyl)-1H-pyrrole-3-carboxylic acid；5-(4-chlorophenyl)-2-methyl-1-(4-sulfamoylphenyl)pyrrole-3-carboxylic acid
• 化学式: C₁₈H₁₅ClN₂O₄S
• 分子量: 390.847
• InChiKey: MLVCEWBLMXMCLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-2-methyl-1-(4-sulfamoylphenyl)-1H-3-carboxylic acid 、 N-乙基甲基胺 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 反应 0.17h， 生成 5-(4-chlorophenyl)-N-ethyl-N,2-dimethyl-1-(4-sulfamoylphenyl)-1H-pyrrole-3-carboxamide
  参考文献：
  名称：

  Discovery of 4-(5-(4-Chlorophenyl)-2-methyl-3-propionyl-1H-pyrrol-1-yl)benzenesulfonamide (A-867744) as a Novel Positive Allosteric Modulator of the α7 Nicotinic Acetylcholine Receptor

  摘要：

  The discovery of a series of pyrrole-sulfonamides as positive allosteric modulators (PAM) of alpha 7 nAChRs is described. Optimization of this series led to the identification of 19 (A-867744), a novel type II PAM with good potency and selectivity. Compound 19 showed acceptable pharmacokinetic profile across species and brain levels sufficient to modulate 0 nAChRs. In a rodent model of sensory gating, 19 normalized gating deficits. These results suggest that 19 represents a novel class of molecules capable of allosteric modulation of the 0 nAChRs.

  DOI：

  10.1021/jm9003818
• 作为产物：
  描述：

  disodium 5-(4-chloro-phenyl)-2-methyl-1-(4-sulfamoyl-phenyl)-1H-pyrrole-3-carboxylate 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 以744 mg的产率得到5-(4-chlorophenyl)-2-methyl-1-(4-sulfamoylphenyl)-1H-3-carboxylic acid
  参考文献：
  名称：

  Discovery of 4-(5-(4-Chlorophenyl)-2-methyl-3-propionyl-1H-pyrrol-1-yl)benzenesulfonamide (A-867744) as a Novel Positive Allosteric Modulator of the α7 Nicotinic Acetylcholine Receptor

  摘要：

  The discovery of a series of pyrrole-sulfonamides as positive allosteric modulators (PAM) of alpha 7 nAChRs is described. Optimization of this series led to the identification of 19 (A-867744), a novel type II PAM with good potency and selectivity. Compound 19 showed acceptable pharmacokinetic profile across species and brain levels sufficient to modulate 0 nAChRs. In a rodent model of sensory gating, 19 normalized gating deficits. These results suggest that 19 represents a novel class of molecules capable of allosteric modulation of the 0 nAChRs.

  DOI：

  10.1021/jm9003818

文献信息

• PYRROLE DERIVATIVES AND THEIR METHODS OF USE
  申请人：Faghih Ramin

  公开号：US20080064695A1

  公开（公告）日：2008-03-13

  The invention relates to a series of substituted pyrrole derivatives, compositions comprising the same, and methods of treating conditions and disorders using such compounds and compositions.

  本发明涉及一系列取代吡咯衍生物，包括这些衍生物的组合物以及使用这些化合物和组合物治疗疾病和疾病的方法。
• Pyrrole Derivatives and Their Methods of Use
  申请人：Faghih Ramin

  公开号：US20100216748A1

  公开（公告）日：2010-08-26

  The invention relates to a series of substituted pyrrole derivatives, compositions comprising the same, and methods of treating conditions and disorders using such compounds and compositions.

  本发明涉及一系列取代吡咯衍生物，包括这些衍生物的组合物以及使用这些化合物和组合物治疗疾病和障碍的方法。
• WO2008/2974
  申请人：——

  公开号：——

  公开（公告）日：——
• US7741364B2
  申请人：——

  公开号：US7741364B2

  公开（公告）日：2010-06-22
• US8609713B2
  申请人：——

  公开号：US8609713B2

  公开（公告）日：2013-12-17