N-(3-phenylpropyl)-1,2,3,4-tetrahydronaphthalen-2-amine | 117145-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: N-(3-phenylpropyl)-1,2,3,4-tetrahydronaphthalen-2-amine
• 英文别名: N-3,4-benzocyclohexyl-3-phenylpropylamine；(3-Phenyl-propyl)-(1,2,3,4-tetrahydro-naphthalen-2-yl)-amine
• CAS: 117145-86-5
• 化学式: C₁₉H₂₃N
• 分子量: 265.398
• InChiKey: CEMUKLXXZBFFNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-苯基-1-丙胺 、 β-四氢萘酮 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以84%的产率得到N-(3-phenylpropyl)-1,2,3,4-tetrahydronaphthalen-2-amine
  参考文献：
  名称：

  负的GluN2B NMDA受体的变构调节剂，其苯乙胺结构嵌入环扩展和环收缩的支架中。

  摘要：

  制备了一组具有构象受限的苯乙胺亚结构的GluN2B NMDA受体拮抗剂，并进行了药理学评估。苯乙胺的亚结构包埋在扩环的3-苯甲唑啉4和缩合的四氮杂胺6和茚满胺7中。配体4、6和7是通过仲胺11的还原烷基化，酮12和16的还原胺化以及亲核性合成的Nosylates 14和17的取代。3-benzazocine 4d（Ki = 32 nM）的中等GluN2B亲和力在两电极电压下转化为中等的细胞保护活性（IC50 = 890 nM）和中等的离子通道抑制（10％时为60％）。表达GluN1a / GluN2B的卵母细胞的钳位实验。尽管某些四氢化萘胺6和茚满胺7具有很高的GluN2B亲和力（例如Ki（7f）= 3.2 nM），它们不能抑制谷氨酸/甘氨酸诱导的细胞毒性。3-苯甲唑啉4，四氢萘胺6和茚满胺7的低细胞保护活性归因于苯环和/或苄基位置上缺少的OH部分。对接研究表明，新型GluN2B配体采用与Ro

  DOI：

  10.1016/j.ejmech.2020.112138

文献信息

• 2-(Alkylamino)tetralin derivatives: interaction with 5-HT1A serotonin binding sites
  作者：Noreen Naiman、Robert A. Lyon、Amy E. Bullock、Laura T. Rydelek、Milt Titeler、Richard A. Glennon

  DOI：10.1021/jm00121a045

  日期：1989.1

  8-Hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT) is a selective 5-HT1A serotonin agonist. Derivatives of 8-OH-DPAT with amine substituents larger or more bulky than n-propyl appear to be inactive in a presynaptic biochemical assay measuring agonist-induced feedback inhibition of 5-HT synthesis but have never been examined in brain binding assays. A series of N-phenylalkyl derivatives of 8-methoxy-2-aminotetralin was evaluated at [3H]-8-OH-DPAT-labeled 5-HT1A sites in rat brain hippocampal membranes. All of the phenylalkyl derivatives displayed significant affinity for these sites and, of the agents examined, the 3-phenylpropyl 8-hydroxy analogue appears to be optimal and had an affinity (Ki = 1.9 nM) comparable to that of 8-OH-DPAT (Ki = 1.2 nM). In addition, the presence of an oxygen-containing substituent at the 8-position of the tetralin ring is not necessary for good affinity, and secondary amines and tertiary amines displayed equal affinity at central 5-HT1A binding sites. 5-HT1A sites are found both pre- and postsynaptically; thus, differences observed in the biochemical assay as compared to the results of the present binding study could be due to different structural requirements of these two receptors. This seems unlikely, however, because there was little difference in the affinities of several selected analogues for striatal versus hippocampal binding sites. Because we have now demonstrated that amine substituents larger than propyl, and an unsubstituted 8-position, are well tolerated by central 5-HT1A sites, future studies aimed at the development of new serotonergic tetralin analogues need not be limited to N-propyl or 8-hydroxy derivatives of 2-aminotetralin.
• SIGMA RECEPTOR LIGANDS AND THE USE THEREOF
  申请人：VIRGINIA COMMONWEALTH UNIVERSITY

  公开号：EP0591426A1

  公开（公告）日：1994-04-13
• US6057371A
  申请人：——

  公开号：US6057371A

  公开（公告）日：2000-05-02
• [EN] SIGMA RECEPTOR LIGANDS AND THE USE THEREOF
  申请人：——

  公开号：WO1991009594A1

  公开（公告）日：1991-07-11

  [EN] The invention relates to methods for the treatment of schizophrenia or other psychoses by administering a pharmaceutical composition comprising an effective amount of certain sigma receptor ligands to a patient in need of such treatment. The invention further relates to novel sigma receptor ligands having high binding to the sigma receptor and pharmaceutical compositions thereof.
  [FR] Procédés de traitement de la schizophrénie ou d'autres psychoses, par administration d'une composition pharmaceutique comprenant une quantité efficace de certains ligands de récepteur sigma, à un patient nécessitant un tel traitement. L'invention concerne également de nouveaux ligands de récepteur sigma, présentant une liaison élevée aux récepteurs sigma, ainsi que leurs compositions pharmaceutiques.
• Negative allosteric modulators of the GluN2B NMDA receptor with phenylethylamine structure embedded in ring-expanded and ring-contracted scaffolds
  作者：Louisa Temme、Elena Bechthold、Julian A. Schreiber、Sandeep Gawaskar、Dirk Schepmann、Dina Robaa、Wolfgang Sippl、Guiscard Seebohm、Bernhard Wünsch

  DOI：10.1016/j.ejmech.2020.112138

  日期：2020.3

  A set of GluN2B NMDA receptor antagonists with conformationally restricted phenylethylamine substructure was prepared and pharmacologically evaluated. The phenylethylamine substructure was embedded in ring expanded 3-benzazocines 4 as well as ring-contracted tetralinamines 6 and indanamines 7. The ligands 4, 6 and 7 were synthesized by reductive alkylation of secondary amine 11, reductive amination

  制备了一组具有构象受限的苯乙胺亚结构的GluN2B NMDA受体拮抗剂，并进行了药理学评估。苯乙胺的亚结构包埋在扩环的3-苯甲唑啉4和缩合的四氮杂胺6和茚满胺7中。配体4、6和7是通过仲胺11的还原烷基化，酮12和16的还原胺化以及亲核性合成的Nosylates 14和17的取代。3-benzazocine 4d（Ki = 32 nM）的中等GluN2B亲和力在两电极电压下转化为中等的细胞保护活性（IC50 = 890 nM）和中等的离子通道抑制（10％时为60％）。表达GluN1a / GluN2B的卵母细胞的钳位实验。尽管某些四氢化萘胺6和茚满胺7具有很高的GluN2B亲和力（例如Ki（7f）= 3.2 nM），它们不能抑制谷氨酸/甘氨酸诱导的细胞毒性。3-苯甲唑啉4，四氢萘胺6和茚满胺7的低细胞保护活性归因于苯环和/或苄基位置上缺少的OH部分。对接研究表明，新型GluN2B配体采用与Ro