2-chloro-10-(3-(4-phenylpiperazin-1-yl)propyl)-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: 2-chloro-10-(3-(4-phenylpiperazin-1-yl)propyl)-10H-phenothiazine
• 英文别名: 2-Chloro-10-[3-(4-phenylpiperazin-1-yl)propyl]phenothiazine；2-chloro-10-[3-(4-phenylpiperazin-1-yl)propyl]phenothiazine
• 化学式: C₂₅H₂₆ClN₃S
• 分子量: 436.021
• InChiKey: TXRYMBMFAYFLJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯吩噻嗪 在 sodium hydride 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.33h， 生成 2-chloro-10-(3-(4-phenylpiperazin-1-yl)propyl)-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

• Phenothiazine derivatives having CaM inhibitory activity
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US10035795B1

  公开（公告）日：2018-07-31

  The present invention provides a phenothiazine derivative or a pharmaceutically acceptable salt thereof, a method of preparing a compound selected therefrom and a pharmaceutical composition containing the compound as an active ingredient. The phenothiazine derivative according to the present invention has an effect of inhibiting calmodulin (CaM; calcium-modulated protein) and thus helps cell death by maintaining the intracellular level of calcium in lung cancer cells at high concentration. Accordingly, the phenothiazine derivative according to the present invention can be usefully used to prevent or treat malignant tumors such as lung cancer.

  本发明提供了一种苯并噻嗪衍生物或其药学上可接受的盐，一种从中选择化合物的制备方法以及含有该化合物作为活性成分的制药组合物。根据本发明，苯并噻嗪衍生物具有抑制钙调蛋白酶（CaM；钙调节蛋白）的作用，从而通过保持肺癌细胞内钙离子的浓度高来帮助细胞死亡。因此，根据本发明的苯并噻嗪衍生物可被有用地用于预防或治疗恶性肿瘤，如肺癌。
• 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.