1-[(chroman-2-yl)methyl]-4-benzylpiperazine

• 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: 1-[(chroman-2-yl)methyl]-4-benzylpiperazine
• 英文别名: 1-Benzyl-4-chroman-2-ylmethyl-piperazine；1-benzyl-4-(3,4-dihydro-2H-chromen-2-ylmethyl)piperazine
• 化学式: C₂₁H₂₆N₂O
• 分子量: 322.45
• InChiKey: AJZBPCAHQHCXMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟甲基苯并二氢吡喃 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 1-[(chroman-2-yl)methyl]-4-benzylpiperazine
  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

• Synthesis and structure–activity relationships of novel arylalkyl 4-benzyl piperazine derivatives as σ site selective ligands
  作者：S Younes

  DOI：10.1016/s0223-5234(00)00113-6

  日期：2000.1

  Continuing our previous work that established that some chromones substituted by an aryl alkyl piperazino alkyl side chain are potent and selective sigma ligands and could be interesting in the treatment of psychosis, we synthesized 60 new compounds, replacing the chromone moiety by various cyclic systems. Many derivatives bind to the sigma sites in the nanomolar range and are generally selective in comparison

  继续我们先前的工作，即确定被芳基烷基哌嗪子烷基侧链取代的某些色酮是有效的选择性σ配体，在精神病治疗中可能是令人感兴趣的，我们合成了60种新化合物，用各种环状系统取代了色酮部分。许多衍生物与纳摩尔范围内的sigma位点结合，与5HT（1A）和D（2）受体相比通常具有选择性。这些系列中最有效的配体之一，是1-（2-萘甲基）-4-苄基哌嗪29，已在各种药理试验中得到了研究。尽管它在治疗精神病方面没有潜力，但我们获得的结果证实了数据，表明这些衍生物可能在炎性疾病的治疗中令人感兴趣。
• Phenoyalkylpiperazine derivatives
  申请人：Adir Et Compagnie

  公开号：US05668138A1

  公开（公告）日：1997-09-16

  A compound selected from those of formula (I): ##STR1## where RA, RB, RC, RD, A, n, X, Y and Ar are defined in the description, and a medicinal product comprising the same for treating a mammal afflicted with a disease associated with sigma receptors.

  从公式（I）中选择的化合物：##STR1##其中RA、RB、RC、RD、A、n、X、Y和Ar在说明中定义，以及包含相同化合物的药物产品，用于治疗患有与西格玛受体相关的疾病的哺乳动物。
• Benzopyran derivatives
  申请人：Adir et Compagnie

  公开号：US05691340A1

  公开（公告）日：1997-11-25

  A compound selected from those of formula (I): ##STR1## where RA, RB, RC, RD, A, n, X, Y and Ar are defined in the description, and a medicinal product comprising the same for treating a mammal afflicted with a disease associated with sigma receptors.

  一种从化学式（I）所示的化合物中选择的化合物：##STR1## 其中RA、RB、RC、RD、A、n、X、Y和Ar在描述中有定义，以及包含它的药物制剂，用于治疗患有与西格玛受体相关的疾病的哺乳动物。
• Nouveaux dérivés du benzopyrane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：ADIR ET COMPAGNIE

  公开号：EP0702010A1

  公开（公告）日：1996-03-20

  Dérivés de formule générale (I) : où RA, RB, RC, RD, A, n, X, Y, et Ar sont définis dans la description. Médicaments.

  通式(I)的衍生物 ： 其中 RA、RB、RC、RD、A、n、X、Y 和 Ar 的定义见说明。 药物。
• Identification and SAR around N-{2-[4-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-[1,4]diazepan-1-yl]-ethyl}-2-phenoxy-nicotinamide, a selective α2C adrenergic receptor antagonist
  作者：Snahel D. Patel、Wendy M. Habeski、Hyunsuk Min、Jiansu Zhang、Robin Roof、Bradley Snyder、Gary Bora、Brian Campbell、Cheryl Li、Debra Hidayetoglu、Douglas S. Johnson、Archana Chaudhry、Maura E. Charlton、Natasha M. Kablaoui

  DOI：10.1016/j.bmcl.2008.08.055

  日期：2008.10

  The discovery of the CNS-penetrant and selective alpha(2C) adrenergic receptor antagonist N-2-[4-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-[1,4]diazepan-1-yl]-ethyl}-2-phenoxy-nicotinamide, 13 is described. Structure - activity studies demonstrate the structural requirements for binding affinity, functional activity, and selectivity over other alpha(2)-AR subtypes. (C) 2008 Elsevier Ltd. All rights reserved.