Benzyl-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine; hydrochloride | 150871-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: Benzyl-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine; hydrochloride
• 英文别名: N-Benzyl-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine--hydrogen chloride (1/1)；N-benzyl-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride
• CAS: 150871-46-8
• 化学式: C₁₈H₂₁NO*ClH
• 分子量: 303.832
• InChiKey: HTAKGXNCLQDYQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Benzyl-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine; hydrochloride 在 盐酸 、 lithium aluminium tetrahydride 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 生成 5-methoxy-2-[N-(2-aminoethyl)-N-benzylamino]tetralin
  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

文献信息

• Synthesis and Antifungal Activities of Novel 2-Aminotetralin Derivatives
  作者：Bin Yao、Haitao Ji、Yongbin Cao、Youjun Zhou、Jü Zhu、Jiaguo Lü、Yaowu Li、Jun Chen、Canhui Zheng、Yuanying Jiang、Rongmei Liang、Hui Tang

  DOI：10.1021/jm0701167

  日期：2007.11.1

  Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoli ne ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14 alpha-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.
• Structural analogues of 5-OMe-BPAT: synthesis and interactions with dopamine D2, D3, and serotonin 5-HT1A receptors
  作者：Evert J. Homan、Esther Kroodsma、Swier Copinga、Lena Unelius、Nina Mohell、Håkan V. Wikström、Cor J. Grol

  DOI：10.1016/s0968-0896(99)00039-5

  日期：1999.6

  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.