5-(2-amino-5-chlorophenyl)-1H-pyrrole-2-carboxylic acid methylamide | 1072150-17-4

• 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-(2-amino-5-chlorophenyl)-1H-pyrrole-2-carboxylic acid methylamide
• 英文别名: QFF200；5-(2-amino-5-chlorophenyl)-N-methyl-1H-pyrrole-2-carboxamide
• CAS: 1072150-17-4
• 化学式: C₁₂H₁₂ClN₃O
• 分子量: 249.7
• InChiKey: ZYBVIUCTJJUXFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-(5-chloro-2-nitrophenyl)-1H-pyrrole-2-carboxylic acid methylamide 在 铁粉 、 iron(II) sulfate 作用下， 生成 5-(2-amino-5-chlorophenyl)-1H-pyrrole-2-carboxylic acid methylamide
  参考文献：
  名称：

  新型 5-苯基吡咯-甲酰胺衍生物的核磁共振和构象研究

  摘要：

  22 5-(5-取代-2-硝基苯基)-1H-吡咯-2-甲酰胺、22 5-(5-取代-2-氨基苯基)-1H-吡咯-2-甲酰胺和 1H 和 13C NMR 共振9 5-苯基-1H-吡咯-2-甲酰胺完全使用一维和二维实验（DEPT、gs-HMQC和gs-HMBC）的协同应用进行分配。NOE 研究和构象分析证实了此类化合物的优选构象。版权所有 © 2009 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.2524

文献信息

• NMR and conformational studies of new 5-phenylpyrrole-carboxamide derivatives
  作者：Luisa C. López-Cara、M. José Pineda de las Infantas、M. Dora Carrión、M. Encarnación Camacho、Miguel A. Gallo、Antonio Espinosa、Antonio Entrena

  DOI：10.1002/mrc.2524

  日期：2009.12

  The 1H and 13C NMR resonances of 22 5‐(5‐substituted‐2‐nitrophenyl)‐1H‐pyrrole‐2‐carboxamides, 22 5‐(5‐substituted‐2‐aminophenyl)‐1H‐pyrrole‐2‐carboxamides, and 9 5‐phenyl‐1H‐pyrrole‐2‐carboxamides were assigned completely using the concerted application of one‐ and two‐dimensional experiments (DEPT, gs‐HMQC and gs‐HMBC). NOE studies and conformational analysis confirm the preferred conformations of

  22 5-(5-取代-2-硝基苯基)-1H-吡咯-2-甲酰胺、22 5-(5-取代-2-氨基苯基)-1H-吡咯-2-甲酰胺和 1H 和 13C NMR 共振9 5-苯基-1H-吡咯-2-甲酰胺完全使用一维和二维实验（DEPT、gs-HMQC和gs-HMBC）的协同应用进行分配。NOE 研究和构象分析证实了此类化合物的优选构象。版权所有 © 2009 John Wiley & Sons, Ltd.
• Phenylpyrrole derivatives as neural and inducible nitric oxide synthase (nNOS and iNOS) inhibitors
  作者：Luisa C. López Cara、M. Encarnación Camacho、M. Dora Carrión、Víctor Tapias、Miguel A. Gallo、Germaine Escames、Darío Acuña-Castroviejo、Antonio Espinosa、Antonio Entrena

  DOI：10.1016/j.ejmech.2008.11.013

  日期：2009.6

  We have previously described a series of 3-phenyl-4,5-dihydro-1H-pyrazole derivatives as moderately potent nNOS inhibitors. As a follow up of these studies, several new 5-phenyl-1H-pyrrole-2-carboxamide derivatives have been synthesized, and their biological evaluation as in vitro inhibitors of both neural and inducible Nitric Oxide Synthase (nNOS and iNOS) is described. Some of these compounds show good iNOS/nNOS selectivity and the more potent compounds 5-(2-aminophenyl)-1H-pyrrole-2-carboxilic acid methylamide (QFF205) and cyclopentylamide (QFF212) have been tested as regulators of the in vivo nNOS and iNOS activity. Both compounds prevented the increment of the inducible NOS activity in both cytosol (iNOS) and mitochondria (i-mtNOS) observed in the MPTP model of Parkinson's disease. (C) 2008 Elsevier Masson SAS. All rights reserved.