2-methyl-5-[4-(fluoro)phenyl]-1-[2-(trifluoromethyl)phenyl]-1H-pyrrole | 1258428-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-methyl-5-[4-(fluoro)phenyl]-1-[2-(trifluoromethyl)phenyl]-1H-pyrrole
• 英文别名: 2-(4-Fluorophenyl)-5-methyl-1-[2-(trifluoromethyl)phenyl]pyrrole
• CAS: 1258428-38-4
• 化学式: C₁₈H₁₃F₄N
• 分子量: 319.302
• InChiKey: DPYLWXXONVFPPK-UHFFFAOYSA-N

物化性质

• 熔点：
  197 °C
• 沸点：
  392.1±42.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[4-(氟)-苯基]戊烷-1,4-二酮 、 邻氨基三氟甲苯 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 160.0 ℃ 、1.03 MPa 条件下， 反应 0.5h， 以70%的产率得到2-methyl-5-[4-(fluoro)phenyl]-1-[2-(trifluoromethyl)phenyl]-1H-pyrrole
  参考文献：
  名称：

  Identification of a novel pyrrole derivative endowed with antimycobacterial activity and protection index comparable to that of the current antitubercular drugs streptomycin and rifampin

  摘要：

  A hit optimization procedure based on isosteric and bioisosteric replacement of decorating groups at both the N1 and the C5 phenyl rings of 1,5-diarylpyrroles led to identification of 4-((1-(4-fluorophenyl)-2-methyl- 5-(4-(methylthio) phenyl)-1H-pyrrol-3-yl) methyl) thiomorpholine that is characterized by a very high activity toward both Mycobacterium tuberculosis 103471 and H37Rv strains (MIC values of 0.125 mu g/mL), and a safe profile in terms of cytotoxicity (CC(50) of > 128 mu g/mL) and protection index (> 1000). Antitubercular activity and protection index of the new compound are comparable to those found for the current antitubercular drugs streptomycin and rifampin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.006

文献信息

• Heterocyclic Carboxamide Compounds as Steroid Nuclear Receptors Ligands
  申请人：Flatt Brenton T.

  公开号：US20110144128A1

  公开（公告）日：2011-06-16

  Heterocyclic carboxamide compounds are described herein as being useful in modulating the activity of steroid nuclear receptors. Pharmaceutical compositions containing the compounds, methods of using the compounds and processes for making the compounds are also described.

  本文介绍了杂环羧酰胺化合物作为调节类固醇核受体活性的有用物质。还描述了含有这些化合物的制药组合物，使用这些化合物的方法以及制造这些化合物的过程。
• US8026237B2
  申请人：——

  公开号：US8026237B2

  公开（公告）日：2011-09-27
• Identification of a novel pyrrole derivative endowed with antimycobacterial activity and protection index comparable to that of the current antitubercular drugs streptomycin and rifampin
  作者：Mariangela Biava、Giulio Cesare Porretta、Giovanna Poce、Claudio Battilocchio、Salvatore Alfonso、Alessandro De Logu、Nadia Serra、Fabrizio Manetti、Maurizio Botta

  DOI：10.1016/j.bmc.2010.09.006

  日期：2010.11.15

  A hit optimization procedure based on isosteric and bioisosteric replacement of decorating groups at both the N1 and the C5 phenyl rings of 1,5-diarylpyrroles led to identification of 4-((1-(4-fluorophenyl)-2-methyl- 5-(4-(methylthio) phenyl)-1H-pyrrol-3-yl) methyl) thiomorpholine that is characterized by a very high activity toward both Mycobacterium tuberculosis 103471 and H37Rv strains (MIC values of 0.125 mu g/mL), and a safe profile in terms of cytotoxicity (CC(50) of > 128 mu g/mL) and protection index (> 1000). Antitubercular activity and protection index of the new compound are comparable to those found for the current antitubercular drugs streptomycin and rifampin. (C) 2010 Elsevier Ltd. All rights reserved.