1-(3,4-dichlorophenyl)-N-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-4-methyl-3-oxo-2H-quinoxaline-6-carboxamide | 1350451-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,4-dichlorophenyl)-N-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-4-methyl-3-oxo-2H-quinoxaline-6-carboxamide
• CAS: 1350451-45-4
• 化学式: C₂₈H₂₉Cl₂N₅O₃
• 分子量: 554.476
• InChiKey: ZXYWAUPKMQONSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氟-3-硝基苯甲酸甲酯 在 吡啶 、 4-二甲氨基吡啶 、 氯化亚砜 、 trans-bis(triphenylphosphine)palladium dichloride 、 palladium on activated charcoal 、 水 、 氢气 、 sodium hydride 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 potassium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 1,2-二氯乙烷 、 甲苯 、 丁酮 为溶剂， 反应 92.0h， 生成 1-(3,4-dichlorophenyl)-N-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]-4-methyl-3-oxo-2H-quinoxaline-6-carboxamide
  参考文献：
  名称：

  A novel potential therapeutic avenue for autism: Design, synthesis and pharmacophore generation of SSRIs with dual action

  摘要：

  Autism symptoms are currently modulated by Selective Serotonin Reuptake Inhibitors (SSRIs). SSRIs slow onset of action limits their efficiency. The established synergistic activity of SSRIs and 5HT(1B/1D) autoreceptors antagonists motivated us to incorporate SSRIs and 5HT(1B/1D) antagonists in one 'hybrid' molecule. A library of virtual 'hybrid' molecules was designed using the tethering technique. A pharmacophore model was generated derived from 16 structurally diverse SSRIs (K-i = 0.013-5000 nM) and used as 3D query. Compounds with fit values (>= 2) were chosen for synthesis and subsequent in vitro biological evaluation. Our pharmacophore model is a promising milestone to a class of SSRIs with dual action. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.046

文献信息

• A novel potential therapeutic avenue for autism: Design, synthesis and pharmacophore generation of SSRIs with dual action
  作者：Ola M. Ghoneim、Diaa A. Ibrahim、Ibrahim M. El-Deeb、So Ha Lee、Raymond G. Booth

  DOI：10.1016/j.bmcl.2011.09.046

  日期：2011.11

  Autism symptoms are currently modulated by Selective Serotonin Reuptake Inhibitors (SSRIs). SSRIs slow onset of action limits their efficiency. The established synergistic activity of SSRIs and 5HT(1B/1D) autoreceptors antagonists motivated us to incorporate SSRIs and 5HT(1B/1D) antagonists in one 'hybrid' molecule. A library of virtual 'hybrid' molecules was designed using the tethering technique. A pharmacophore model was generated derived from 16 structurally diverse SSRIs (K-i = 0.013-5000 nM) and used as 3D query. Compounds with fit values (>= 2) were chosen for synthesis and subsequent in vitro biological evaluation. Our pharmacophore model is a promising milestone to a class of SSRIs with dual action. (C) 2011 Elsevier Ltd. All rights reserved.