(S)-1-(4-fluorophenyl)-2-(1H-imidazol-1-yl)ethyl 4-(4-chlorophenyl)piperazine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (S)-1-(4-fluorophenyl)-2-(1H-imidazol-1-yl)ethyl 4-(4-chlorophenyl)piperazine-1-carboxylate
• 英文别名: [(1S)-1-(4-fluorophenyl)-2-imidazol-1-ylethyl] 4-(4-chlorophenyl)piperazine-1-carboxylate
• 化学式: C₂₂H₂₂ClFN₄O₂
• 分子量: 428.894
• InChiKey: YNQKQNLALVYYHR-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-氟苯基)-2-(1H-咪唑-1-基)-乙酮 在 甲酸 、 Noyori's catalyst 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 38.0h， 生成 (S)-1-(4-fluorophenyl)-2-(1H-imidazol-1-yl)ethyl 4-(4-chlorophenyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Discovery of in vitro antitubercular agents through in silico ligand-based approaches

  摘要：

  The development of new anti-tubercular agents represents a constant challenge mostly due to the insurgency of resistance to the currently available drugs. In this study, a set of 60 molecules were selected by screening the Asinex and the ZINC collections and an in house library by means of in silico ligand-based approaches. Biological assays in Mycobacterium tuberculosis H37Ra ATCC 25177 strain highlighted (+/-)-1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)ethyl-4-(3,4-dichlorophenyl)piperazine-1-carboxylate (5i) and 3-(4-chlorophenyl)-5-(2,4-dimethylpyrimidin-5-yl)-2-methylpyrazolo[1.5-a]pyrimidin-7(4H)-one (42) as the most potent compounds, having a Minimum Inhibitory Concentration (MIC) of 4 and 2 mu g/mL respectively. These molecules represent a good starting point for further optimization of effective anti-TB agents. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.05.032

文献信息

• Discovery of in vitro antitubercular agents through in silico ligand-based approaches
  作者：Daniela De Vita、Fabiana Pandolfi、Roberto Cirilli、Luigi Scipione、Roberto Di Santo、Laura Friggeri、Mattia Mori、Diego Fiorucci、Giorgio Maccari、Robert Selwyne Arul Christopher、Claudio Zamperini、Valentina Pau、Alessandro De Logu、Silvano Tortorella、Maurizio Botta

  DOI：10.1016/j.ejmech.2016.05.032

  日期：2016.10

  The development of new anti-tubercular agents represents a constant challenge mostly due to the insurgency of resistance to the currently available drugs. In this study, a set of 60 molecules were selected by screening the Asinex and the ZINC collections and an in house library by means of in silico ligand-based approaches. Biological assays in Mycobacterium tuberculosis H37Ra ATCC 25177 strain highlighted (+/-)-1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)ethyl-4-(3,4-dichlorophenyl)piperazine-1-carboxylate (5i) and 3-(4-chlorophenyl)-5-(2,4-dimethylpyrimidin-5-yl)-2-methylpyrazolo[1.5-a]pyrimidin-7(4H)-one (42) as the most potent compounds, having a Minimum Inhibitory Concentration (MIC) of 4 and 2 mu g/mL respectively. These molecules represent a good starting point for further optimization of effective anti-TB agents. (C) 2016 Elsevier Masson SAS. All rights reserved.