2-methyl-3-[(thiomorpholin-4-yl)-methyl]-5-[4-(methylthio)phenyl]-1-[4-(fluoro)phenyl]1H-pyrrole | 1135011-43-6

• 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-3-[(thiomorpholin-4-yl)-methyl]-5-[4-(methylthio)phenyl]-1-[4-(fluoro)phenyl]1H-pyrrole
• 英文别名: 4-[[1-(4-Fluorophenyl)-2-methyl-5-(4-methylsulfanylphenyl)pyrrol-3-yl]methyl]thiomorpholine
• CAS: 1135011-43-6
• 化学式: C₂₃H₂₅FN₂S₂
• 分子量: 412.595
• InChiKey: UULZVHSCPMWVSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  硫代吗啉 、 聚合甲醛 、 2-methyl-5-[4-(methylthio)phenyl]-1-[4-(fluoro)phenyl]-1H-pyrrole 在 溶剂黄146 、 sodium hydroxide 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 12.0h， 以92%的产率得到2-methyl-3-[(thiomorpholin-4-yl)-methyl]-5-[4-(methylthio)phenyl]-1-[4-(fluoro)phenyl]1H-pyrrole
  参考文献：
  名称：

  Pyrrole compounds as inhibitors of mycrobacteria, synthesis thereof and intermediates thereto

  摘要：

  本发明涉及具有一般公式3的化合物的合成、中间体及其用途。

  公开号：

  EP2045237A1

文献信息

• 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.
• PYRROLE COMPOUNDS AS INHIBITORS OF MYCOBACTERIA, SYNTHESIS THEREOF ANS INTERMEDIATES THERETO
  申请人：Universita'Degli Studi di Roma "La Sapienza"

  公开号：EP2195289B1

  公开（公告）日：2013-06-19
• PYRROLE COMPOUNDS AS INHIBITORS OF MYCOBACTERIA, SYNTHESIS THEREOF AND INTERMEDIATES THERETO
  申请人：Biava Mariangela

  公开号：US20100197672A1

  公开（公告）日：2010-08-05

  The present invention relates to a compound having the general formula (3): synthesis, intermediates and uses thereof.
• US8304410B2
  申请人：——

  公开号：US8304410B2

  公开（公告）日：2012-11-06
• [EN] PYRROLE COMPOUNDS AS INHIBITORS OF MYCOBACTERIA, SYNTHESIS THEREOF ANS INTERMEDIATES THERETO<br/>[FR] COMPOSÉS DU PYRROLE EN TANT QU'INHIBITEURS DE MYCOBACTÉRIES, LEUR SYNTHÈSE ET INTERMÉDIAIRES DE CETTE SYNTHÈSE
  申请人：UNIV ROMA

  公开号：WO2009040755A2

  公开（公告）日：2009-04-02

  The present invention relates to a compound having the general formula (3): synthesis, intermediates and uses thereof.