10-(2-(piperidin-2-yl)ethyl)-10H-phenothiazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 10-(2-(piperidin-2-yl)ethyl)-10H-phenothiazine
• 英文别名: 10-(2-Piperidin-2-ylethyl)phenothiazine；10-(2-piperidin-2-ylethyl)phenothiazine
• 化学式: C₁₉H₂₂N₂S
• 分子量: 310.463
• InChiKey: KCQNCMODOHACEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  40.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 10-(2-(piperidin-2-yl)ethyl)-10H-phenothiazine 在 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.5h， 以47%的产率得到10-[2-(1-甲基哌啶-2-基)乙基]吩噻嗪
  参考文献：
  名称：

  Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis

  摘要：

  The neuroleptic drug thioridazine has been recently repositioned as possible anti-tubercular drug. Thioridazine showed anti-tubercular activity against drug resistant mycobacteria but it is endowed with adverse side effects. A small library of thioridazine derivatives has been designed through the replacement of the piperidine and phenothiazine moieties, with the aim to improve the anti-tubercular activity and to reduce the cytotoxic effects. Among the resulting compounds, the indole derivative 12e showed an antimycobacterial activity significantly better than thioridazine and a cytotoxicity 15-fold lower. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.12.042
• 作为产物：
  描述：

  t-butyl 2-(2-bromoethyl)piperidine-1-carboxylate 在 盐酸 、 sodium hydride 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.33h， 生成 10-(2-(piperidin-2-yl)ethyl)-10H-phenothiazine
  参考文献：
  名称：

  Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis

  摘要：

  The neuroleptic drug thioridazine has been recently repositioned as possible anti-tubercular drug. Thioridazine showed anti-tubercular activity against drug resistant mycobacteria but it is endowed with adverse side effects. A small library of thioridazine derivatives has been designed through the replacement of the piperidine and phenothiazine moieties, with the aim to improve the anti-tubercular activity and to reduce the cytotoxic effects. Among the resulting compounds, the indole derivative 12e showed an antimycobacterial activity significantly better than thioridazine and a cytotoxicity 15-fold lower. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.12.042

文献信息

• Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis
  作者：Nicolò Scalacci、Alistair K. Brown、Fernando R. Pavan、Camila M. Ribeiro、Fabrizio Manetti、Sanjib Bhakta、Arundhati Maitra、Darren L. Smith、Elena Petricci、Daniele Castagnolo

  DOI：10.1016/j.ejmech.2016.12.042

  日期：2017.2

  The neuroleptic drug thioridazine has been recently repositioned as possible anti-tubercular drug. Thioridazine showed anti-tubercular activity against drug resistant mycobacteria but it is endowed with adverse side effects. A small library of thioridazine derivatives has been designed through the replacement of the piperidine and phenothiazine moieties, with the aim to improve the anti-tubercular activity and to reduce the cytotoxic effects. Among the resulting compounds, the indole derivative 12e showed an antimycobacterial activity significantly better than thioridazine and a cytotoxicity 15-fold lower. (C) 2016 Elsevier Masson SAS. All rights reserved.