2-{[4-[(1,3-Benzodioxol-5-yl) Methyl]Piperazin-1-yl]methyl }-4-Oxo[4H]-1-Benzopyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-{[4-[(1,3-Benzodioxol-5-yl) Methyl]Piperazin-1-yl]methyl }-4-Oxo[4H]-1-Benzopyran
• 英文别名: 2-[[4-(1,3-Benzodioxol-5-ylmethyl)piperazin-1-yl]methyl]chromen-4-one
• 化学式: C₂₂H₂₂N₂O₄
• 分子量: 378.428
• InChiKey: LTKXEWHGMRUXLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(chloromethyl)-4H-chromen-4-one 、 1-胡椒基哌嗪 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到2-{[4-[(1,3-Benzodioxol-5-yl) Methyl]Piperazin-1-yl]methyl }-4-Oxo[4H]-1-Benzopyran
  参考文献：
  名称：

  Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands

  摘要：

  Starling from a random screening showing that 2-[(4-benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methylenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4'-methoxy benzyl)-1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80001-9

文献信息

• Aminoalkylchromones, leurs procédés de préparation et les compositions qui les contiennent
  申请人：ADIR ET COMPAGNIE

  公开号：EP0580503A1

  公开（公告）日：1994-01-26

  L'invention concerne des composés de formule générale (I) : avec R1, R2, R3, R4, R5, R6 et Z définis dans la description, leurs isomères optiques et leurs sels d'addition à un acide ou une base pharmaceutiquement acceptable. Médicaments.

  本发明涉及通式 (I) 的化合物： 中定义的 R1、R2、R3、R4、R5、R6 和 Z 及其光学异构体，以及它们与药学上可接受的酸或碱的加成盐。药物。
• US5519023A
  申请人：——

  公开号：US5519023A

  公开（公告）日：1996-05-21
• Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands
  作者：Geneviève Baziard-Mouysset、Salouma Younes、Youssef Labssita、Marc Payard、Daniel-Henri Caignard、Marie-Claire Rettori、Pierre Renard、Bruno Pfeiffer、Béatrice Guardiola-Lemaitre

  DOI：10.1016/s0223-5234(98)80001-9

  日期：1998.6

  Starling from a random screening showing that 2-[(4-benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methylenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4'-methoxy benzyl)-1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis. (C) Elsevier, Paris.