N-{2-[Benzyl-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amino]-ethyl}-benzamide | 238411-34-2

• 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-{2-[Benzyl-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amino]-ethyl}-benzamide
• CAS: 238411-34-2
• 化学式: C₂₇H₃₀N₂O₂
• 分子量: 414.547
• InChiKey: IUTWPEWFPJABHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-{2-[Benzyl-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amino]-ethyl}-benzamide 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 为溶剂， 20.0~55.0 ℃ 、405.3 kPa 条件下， 生成 5-methoxy-2-[N-(2-benzamidoethyl)-N-ethylamino]tetralin hydrochloride
  参考文献：
  名称：

  Structural analogues of 5-OMe-BPAT: synthesis and interactions with dopamine D2, D3, and serotonin 5-HT1A receptors

  摘要：

  Several structural analogues of 5-methoxy-2-[N-(2-benzamidoethyl)-N-n-propylamino]tetralin (5-OMe-BPAT, 1), a representative of a series of 2-aminotetralin-derived benzamides with po ten tial atypical antipsychotic properties, were synthesized and evaluated for their ability to bind to dopamine D-2A, D-3, and serotonin 5-HT1A receptors in vitro. The structure-affinity relationships revealed that the aromatic ring of the benzamide moiety of 1 contributes to the high affinities for all three receptor subtypes. Furthermore, 1 may interact with the dopamine D-2 and D-3 receptors through hydrogen bond formation with its carbonyl group. Investigation of the role of the amide hydrogen atom by amide N-alkylation was not conclusive, since conformational aspects may be responsible for the decreased dopaminergic affinities of the N'-alkylated analogues of 1. The effects of the amide modifications on the serotonin 5-HT1A receptor affinity were less pronounced, suggesting that the benzamidoethyl side-chain of 1 as a whole enhances the affinity for this receptor subtype probably through hydrophobic interactions with an accessory binding site. The structural requirements for the substituents at the basic nitrogen atom supported the hypothesis that the 2-aminotetralin moieties of the 2-aminotetralin-derived substituted benzamides may share the same binding sites as the 2-(N, N-di-n-propylamino)tetralins. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00039-5
• 作为产物：
  描述：

  苯甲酰氯 、 5-methoxy-2-[N-(2-aminoethyl)-N-benzylamino]tetralin oxalate 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到N-{2-[Benzyl-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amino]-ethyl}-benzamide
  参考文献：
  名称：

  Structural analogues of 5-OMe-BPAT: synthesis and interactions with dopamine D2, D3, and serotonin 5-HT1A receptors

  摘要：

  Several structural analogues of 5-methoxy-2-[N-(2-benzamidoethyl)-N-n-propylamino]tetralin (5-OMe-BPAT, 1), a representative of a series of 2-aminotetralin-derived benzamides with po ten tial atypical antipsychotic properties, were synthesized and evaluated for their ability to bind to dopamine D-2A, D-3, and serotonin 5-HT1A receptors in vitro. The structure-affinity relationships revealed that the aromatic ring of the benzamide moiety of 1 contributes to the high affinities for all three receptor subtypes. Furthermore, 1 may interact with the dopamine D-2 and D-3 receptors through hydrogen bond formation with its carbonyl group. Investigation of the role of the amide hydrogen atom by amide N-alkylation was not conclusive, since conformational aspects may be responsible for the decreased dopaminergic affinities of the N'-alkylated analogues of 1. The effects of the amide modifications on the serotonin 5-HT1A receptor affinity were less pronounced, suggesting that the benzamidoethyl side-chain of 1 as a whole enhances the affinity for this receptor subtype probably through hydrophobic interactions with an accessory binding site. The structural requirements for the substituents at the basic nitrogen atom supported the hypothesis that the 2-aminotetralin moieties of the 2-aminotetralin-derived substituted benzamides may share the same binding sites as the 2-(N, N-di-n-propylamino)tetralins. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00039-5