N-<2-<2-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>ethoxy>ethyl>phthalimide | 155289-02-4

• 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: N-<2-<2-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>ethoxy>ethyl>phthalimide
• 英文别名: 2-{2-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethoxy]-ethyl}-isoindole-1,3-dione；2-[2-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethoxy]ethyl]isoindole-1,3-dione
• CAS: 155289-02-4
• 化学式: C₂₃H₂₄N₄O₃S
• 分子量: 436.535
• InChiKey: ZNQUBZLVCKKPOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  94.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-<2-<2-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>ethoxy>ethyl>phthalimide 在 一水合肼 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.75h， 生成 2-<2-<2-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>ethoxy>ethyl>-1-isoindolinone
  参考文献：
  名称：

  Effect of Linking Bridge Modifications on the Antipsychotic Profile of Some Phthalimide and Isoindolinone Derivatives

  摘要：

  A series of phthalimide and isoindolinone derivatives bridged to 4-(1,2-benzisothiazo1-3-yl)-1-piperazinyl was prepared. The compounds were evaluated in vitro at dopamine D-2 and serotonin 5-HT1a and 5-HT2 receptors and in vivo for their ability to antagonize the apomorphine-induced climbing response in mice. The effects of bridge length and conformation on the biological activity of these potential antipsychotic agents are discussed. A four-carbon spacer provided optimal activity within the two homologous series. Conformational investigations of the lead compound, isoindolinone 2, were conducted in an attempt to account for the superior activity observed for the butyl derivatives. On the basis of NMR and molecular modeling studies, two types of folded structures were proposed and several conformationally restrained analogues were synthesized. In general, restrictions incorporated within the linking bridge were detrimental to activity.

  DOI：

  10.1021/jm9502201
• 作为产物：
  描述：

  2-[2-(2-氯乙氧基)乙基]-1H-异吲哚-1,3(2H-)-二酮 、 3-(1-哌嗪基)-1,2-苯并异噻唑 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.5h， 生成 N-<2-<2-<4-(1,2-benzisothiazol-3-yl)-1-piperazinyl>ethoxy>ethyl>phthalimide
  参考文献：
  名称：

  Effect of Linking Bridge Modifications on the Antipsychotic Profile of Some Phthalimide and Isoindolinone Derivatives

  摘要：

  A series of phthalimide and isoindolinone derivatives bridged to 4-(1,2-benzisothiazo1-3-yl)-1-piperazinyl was prepared. The compounds were evaluated in vitro at dopamine D-2 and serotonin 5-HT1a and 5-HT2 receptors and in vivo for their ability to antagonize the apomorphine-induced climbing response in mice. The effects of bridge length and conformation on the biological activity of these potential antipsychotic agents are discussed. A four-carbon spacer provided optimal activity within the two homologous series. Conformational investigations of the lead compound, isoindolinone 2, were conducted in an attempt to account for the superior activity observed for the butyl derivatives. On the basis of NMR and molecular modeling studies, two types of folded structures were proposed and several conformationally restrained analogues were synthesized. In general, restrictions incorporated within the linking bridge were detrimental to activity.

  DOI：

  10.1021/jm9502201

文献信息

• [EN] PIPERAZINE AND PIPERIDINE DERIVATIVES, AND THEIR USE AS ANTIPSYCHOTICS
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：WO1993016073A1

  公开（公告）日：1993-08-19

  (EN) The present invention relates to a group of piperazine and piperidine derivatives, to processes for their preparation, to pharmaceutical compositions containing them and to their use in therapy, in particular in the treatment of psychotic disorders.(FR) La présente invention concerne un groupe de dérivés de pipérazine et de pipéridine, leurs procédés de préparation, des compositions pharmaceutiques les contenant et leur utilisation thérapeutique, notamment dans le traitement des maladies psychotiques.
• Effect of Linking Bridge Modifications on the Antipsychotic Profile of Some Phthalimide and Isoindolinone Derivatives
  作者：Mark H. Norman、Douglas J. Minick、Greg C. Rigdon

  DOI：10.1021/jm9502201

  日期：1996.1.1

  A series of phthalimide and isoindolinone derivatives bridged to 4-(1,2-benzisothiazo1-3-yl)-1-piperazinyl was prepared. The compounds were evaluated in vitro at dopamine D-2 and serotonin 5-HT1a and 5-HT2 receptors and in vivo for their ability to antagonize the apomorphine-induced climbing response in mice. The effects of bridge length and conformation on the biological activity of these potential antipsychotic agents are discussed. A four-carbon spacer provided optimal activity within the two homologous series. Conformational investigations of the lead compound, isoindolinone 2, were conducted in an attempt to account for the superior activity observed for the butyl derivatives. On the basis of NMR and molecular modeling studies, two types of folded structures were proposed and several conformationally restrained analogues were synthesized. In general, restrictions incorporated within the linking bridge were detrimental to activity.