2-methyl-3-[(thiomorpholin-4-yl)-methyl]-5-[4-(methylthio)phenyl]-1-[4-(i-propyl)phenyl]-1H-pyrrole | 1135011-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-methyl-3-[(thiomorpholin-4-yl)-methyl]-5-[4-(methylthio)phenyl]-1-[4-(i-propyl)phenyl]-1H-pyrrole
• 英文别名: 4-[[1-(4-Isopropylphenyl)-2-methyl-5-(4-methylsulfanylphenyl)pyrrol-3-yl]methyl]thiomorpholine；4-[[2-methyl-5-(4-methylsulfanylphenyl)-1-(4-propan-2-ylphenyl)pyrrol-3-yl]methyl]thiomorpholine
• CAS: 1135011-66-3
• 化学式: C₂₆H₃₂N₂S₂
• 分子量: 436.685
• InChiKey: QEQFEGYBYJPTTK-UHFFFAOYSA-N

物化性质

• 沸点：
  571.2±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.8
• 氢给体数：
  0
• 氢受体数：
  3

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-(i-propyl)phenyl]-1H-pyrrole 在 溶剂黄146 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以52%的产率得到2-methyl-3-[(thiomorpholin-4-yl)-methyl]-5-[4-(methylthio)phenyl]-1-[4-(i-propyl)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

• 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.