3-[(4-Benzylpiperazin-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: 3-[(4-Benzylpiperazin-1-yl)Methyl]-4-Oxo[4H]-1-Benzopyran
• 英文别名: 3-(4-Benzyl-piperazin-1-ylmethyl)-chromen-4-one；3-[(4-benzylpiperazin-1-yl)methyl]chromen-4-one
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: NXKAXFXPOZEBIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(羟甲基)-4-氧代-4H-1-苯并吡喃 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-[(4-Benzylpiperazin-1-yl)Methyl]-4-Oxo[4H]-1-Benzopyran
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 1-Aralkyl-4-Benzylpiperidine and 1-Aralkyl-4-Benzylpiperazine Derivatives as Potent σ Ligands

  摘要：

  In the attempt to define more accurately structure-affinity relationships for sigma(1) and sigma(2) ligands, we synthesized and tested on sigma subtype receptors a series of aralkyl derivatives of 4-benzylpiperidine, in which the effect of modifications on the aralkyl moiety was studied in a systematic way. The affinity of the compounds here described varied to a great extent, with a sigma(2)/sigma(1), selectivity ranging from 0.1 to 9. Thus, to confirm the ability of the piperazine derivative to bind to sigma(1) receptors in a different way than piperidines, we synthesized and tested a series of piperazine compounds; the comparison of their affinity with that of the corresponding piperidines strongly supports the possibility of a different binding mode. While the compounds here described are on the whole selective for a vs serotonin 5-HT1A and dopamine D-2 receptors, 9aa, 9ba and 9ab possess a remarkable affinity for both a and 5-HT1A receptors, with K-i in the nanomolar range, and are selective with respect to D2 receptors. They displayed also a partial agonist profile in a human 5-HT1A [S-35]GTPgammaS binding assay, suggesting their potential use as atypical antipsychotic agents.

  DOI：

  10.1021/jm049433t

文献信息

• New aminoalkylchromones, processes for the preparation thereof
  申请人：Adir et Compagnie

  公开号：US05519023A1

  公开（公告）日：1996-05-21

  The invention relates to compounds of the general formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and Z are as defined in the description, their optical isomers and their addition salts with a pharmaceutically-acceptable acid or base and medicaments containing the same, useful in the treatment and prevention of stress, anxiety, and related ailments.

  本发明涉及一般式（I）的化合物：##STR1## 其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5，R.sub.6和Z如描述中所定义，它们的光学异构体及其与药学上可接受的酸或碱的加成盐和含有它们的药物，在治疗和预防压力、焦虑和相关疾病方面有用。
• 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