1-(4-(2-((2,4-dimethylphenyl)thio)phenyl)piperazin-1-yl)ethanone

• 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: 1-(4-(2-((2,4-dimethylphenyl)thio)phenyl)piperazin-1-yl)ethanone
• 英文别名: 1-[4-[2-(2,4-Dimethylphenyl)sulfanylphenyl]piperazin-1-yl]ethanone；1-[4-[2-(2,4-dimethylphenyl)sulfanylphenyl]piperazin-1-yl]ethanone
• 化学式: C₂₀H₂₄N₂OS
• 分子量: 340.489
• InChiKey: RTOYXVAUQYVQHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  48.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-(2-((2,4-dimethylphenyl)thio)phenyl)piperazin-1-yl)ethanone 在 水 、 氢溴酸 、 potassium hydroxide 作用下， 以 甲醇 、 醋酸异丙酯 为溶剂， 反应 25.0h， 生成 沃替西汀氢溴酸盐
  参考文献：
  名称：

  Synthesis of vortioxetine via (2-(piperazine-1-yl)phenyl)aniline intermediates

  摘要：

  本发明提供了一种新的合成过程，用于生产治疗抑郁症和焦虑症的药物1-(2-((2,4-二甲基苯基)硫基)苯基)哌嗪（伏地酮），该过程通过(2-(哌嗪-1-基)苯基)苯胺中间体进行。

  公开号：

  EP2894154A1
• 作为产物：
  描述：

  1-乙酰基-4-(2-硝基-苯基)-哌嗪 在 tris-(dibenzylideneacetone)dipalladium(0) 、 硫酸 、 palladium on activated charcoal 、 氢气 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 、 sodium nitrite 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 80.0 ℃ 、275.8 kPa 条件下， 反应 16.0h， 生成 1-(4-(2-((2,4-dimethylphenyl)thio)phenyl)piperazin-1-yl)ethanone
  参考文献：
  名称：

  NEW VORTIOXETINE INTERMEDIATE AND SYNTHESIS PROCESS THEREOF

  摘要：

  本发明提供了一种新的中间体II及其合成方法。该方法包括：(a)首先将化合物I作为原料重氮化，然后卤代化以获得中间体II；以及(b)将中间体II与化合物III反应以获得化合物IV，直接水解所得的化合物IV而不进行分离，从而获得化合物V代表的Vortioxetine。中间体II可用于合成Vortioxetine。

  公开号：

  US20170088530A1

文献信息

• [EN] SYNTHESIS OF VORTIOXETINE VIA (2-(PIPERAZINE-1 -YL)PHENYL)ANILINE INTERMEDIATES<br/>[FR] SYNTHÈSE DE VORTIOXÉTINE VIA DES INTERMÉDIAIRES (2-(PIPÉRAZINE-1-YL)PHÉNYL)ANILINE
  申请人：LEK PHARMACEUTICALS

  公开号：WO2015107057A1

  公开（公告）日：2015-07-23

  The present invention provides a new synthetic process for the production of 1-(2-((2,4- dimethylphenyl)thio)phenyl)piperazine (vortioxetine), a drug for the treatment of depression and anxiety, which is conducted via (2-(piperazine-1-yl)phenyl)aniline intermediates.

  本发明提供了一种新的合成工艺，用于生产治疗抑郁症和焦虑症的药物1-(2-((2,4-二甲基苯基)硫)苯基)哌嗪（伏地苯丁），该合成工艺通过(2-(哌嗪-1-基)苯基)苯胺中间体进行。
• Design, synthesis and biological evaluation of vortioxetine derivatives as new COX-1/2 inhibitors in human monocytes
  作者：Maria Talmon、Raju D. Chaudhari、Hemant Suryavanshi、Nilkanta Chowdhury、Martina Quaregna、Arianna Pin、Angshuman Bagchi、Goutam Biswas、Luigia G. Fresu

  DOI：10.1016/j.bmc.2020.115760

  日期：2020.12

  In order to identify a suitable alternative to non-steroidal anti-inflammatory drugs (NSAIDs) we aimed to develop derivatives of vortioxetine, a multimodal anti-depressive drug that has been shownpreviously to be endowed withanti-inflammatory activity in human monocytes/macrophages. Vortioxetine (1) was synthesized in good yield and different alkyl and aryl derivatives were prepared based on their structural diversity and easy availability. The compounds were tested on human monocytes isolated from healthy donors for theireffect on superoxide anion production and cytokine gene expression, and for COX-1/2 gene expression and activity modulation. Moreover, a docking study was performed to predict the interactions between the synthesized compounds and COX-1 and COX-2. Correlating experimental biological data to the molecular modelling studies, it emerged that among the novel compounds, 6 was endowed of antioxidant and anti-COX-1 activity, vortioxetine and 3 were good antioxidants and mild anti-COX-1/2 inhibitors, while 7 was a good anti-COX-1/2 inhibitor and 11 was more specific versus COX-2.
• US9926286B2
  申请人：——

  公开号：US9926286B2

  公开（公告）日：2018-03-27
• [EN] A PROCESS FOR PREPARATION OF VORTIOXETINE AND POLYMORPHS THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE VORTIOXÉTINE ET DE POLYMORPHES DE CETTE SUBSTANCE
  申请人：MEGAFINE PHARMA P LTD

  公开号：WO2016079751A2

  公开（公告）日：2016-05-26

  The present invention relates to an improved process for preparation of vortioxetine or pharmaceutically acceptable salts thereof. The present invention also relates to new process for the preparation of vortioxetine or pharmaceutically acceptable salts thereof. The present invention further relates to novel polymorphs of vortioxetine hydrobromide and process for preparation thereof.
• [EN] VORTIOXETINE PRODRUGS<br/>[FR] PROMÉDICAMENTS DE VORTIOXÉTINE
  申请人：H LUNDBECK AS

  公开号：WO2017162536A1

  公开（公告）日：2017-09-28

  Prodrugs of vortioxetine are provided