2-氯-10-[2-(1-甲基-2-哌啶基)乙基]-10H-吩噻嗪 | 5060-56-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 中文名称: 2-氯-10-[2-(1-甲基-2-哌啶基)乙基]-10H-吩噻嗪
• 英文名称: 2-chloro-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine
• 英文别名: NCI186055；Chloridazin；(+/-)-2-Chlor-10-[2-(1-methyl-[2]piperidyl)-aethyl]-phenothiazin；Ridazin；2-chloro-10-[2-(1-methylpiperidin-2-yl)ethyl]phenothiazine
• CAS: 5060-56-0
• 化学式: C₂₀H₂₃ClN₂S
• 分子量: 358.935
• InChiKey: SNXMQJGTZHNPCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  31.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934300000

反应信息

• 作为产物：
  描述：

  t-butyl 2-(2-bromoethyl)piperidine-1-carboxylate 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.83h， 生成 2-氯-10-[2-(1-甲基-2-哌啶基)乙基]-10H-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

文献信息

• Synthesen auf dem Phenothiazin-Gebiet. 3. Mitteilung. Neue Phenothiazinderivate
  作者：J.-P. Bourquin、G. Schwarb、G. Gamboni、R. Fischer、L. Ruesch、S. Guldimann、V. Theus、E. Schenker、J. Renz

  DOI：10.1002/hlca.19590420124

  日期：——

  The synthesis and properties of various N- and C-3-substituted derivatives of phenothiazine are described.

  描述了吩噻嗪的各种N-和C-3-取代的衍生物的合成和性质。
• UTILISATION D'UN COMPOSE TRICYCLIQUE POUR PREPARER UN MEDICAMENT POUR TRAITER DES DEGENERESCENCES DU MUSCLE SQUELETTIQUE D'ORIGINE GENETIQUE
  申请人：Association Française contre les Myopathies

  公开号：EP2012793B1

  公开（公告）日：2015-04-08
• [EN] USE OF A TRICYCLIC COMPOUND FOR PREPARING A MEDICINE FOR TREATING SKELETAL MUSCLE DEGENERATION<br/>[FR] UTILISATION D'UN COMPOSE TRICYCLIQUE, POUR LA PREPARATION D'UN MEDICAMENT DESTINE A TRAITER DES DEGENERESCENCES DU MUSCLE SQUELETTIQUE
  申请人：UNIV CLAUDE BERNARD LYON

  公开号：WO2007125246A1

  公开（公告）日：2007-11-08

  [EN] The invention concerns the use of a compound of formula (I) such as defined in Claim 1, for preparing a medicine for treating or preventing conditions corresponding to muscular degeneration of skeletal muscles, such as muscular myopathies of genetic origin, and in particular Duchenne's myopathy, or cachexias.
  [FR] La présente invention concerne l'utilisation d'un composé de formule (I) tel que défini à la revendication 1, pour la préparation d'un médicament destiné à traiter ou prévenir des pathologies correspondant à une dégénérescence musculaire des muscles squelettiques, telles que les myopathies musculaires d'origine génétique, et notamment la myopathie de Duchenne, ou encore les cachexies.
• 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.