5-甲氧基-1,2,3,4-四氢-N-(苯甲基)-2-萘胺 | 136247-07-9

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 5-甲氧基-1,2,3,4-四氢-N-(苯甲基)-2-萘胺
• 中文别名: 5-甲氧基-1,2,3,4-四氢-N-(苯甲基)-2-萘胺(罗替戈汀)；5-甲氧基-1,2,3,4-四氢-N-(苯甲基)-2-萘胺 (罗替戈汀)
• 英文名称: 2-(N-benzylamino)-5-methoxytetralin
• 英文别名: N-benzyl-N-(5-methoxy-1,2,3,4-tatrahydronaphthalen-2-yl)amine；N-benzyl-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amine；N-benzyl-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 136247-07-9
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: OZFLGQHJVWSALN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 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：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  5-甲氧基-1,2,3,4-四氢-N-(苯甲基)-2-萘胺 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 45.0 ℃ 、303.97 kPa 条件下， 反应 1.0h， 生成 5-甲氧基-2-四氢萘胺
  参考文献：
  名称：

  2-Amido-8-methoxytetralins: A series of nonindolic melatonin-like agents

  摘要：

  A series of unsubstituted and methoxy-substituted 2-amidotetralins (4a-q) was prepared and evaluated for their ability to compete for 2-[I-125]iodomelatonin binding to chicken retinal membranes and for their potency to inhibit the calcium-dependent release of [H-3]dopamine from rabbit retina. The lead compound, 2-acetamido-8-methoxytetralin (4j), showed a moderate affinity (K(i) = 46 nM) and potency (IC50 = 1.4 nM) at the melatonin receptor. The structural requirements necessary for optimal agonistic activity at the melatonin receptor are as follows. First, the amido group, which should have a small, nonbranched alkyl group, is essential for affinity, and second, the methoxy substituent at the 8-position of the 2-amidotetralin ring is essential for optimal agonistic activity at the melatonin receptor. We concluded that this series of unsubstituted and methoxy-substituted 2-amidotetralins constitutes a class of nonindolic melatonin-like agents that can be used as pharmacological tools to further characterize melatonin receptors and to elucidate the mode of action of melatonin.

  DOI：

  10.1021/jm00072a008
• 作为产物：
  描述：

  5-甲氧基-2-萘满酮 在 platinum(IV) oxide 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 苯 为溶剂， 反应 19.5h， 生成 5-甲氧基-1,2,3,4-四氢-N-(苯甲基)-2-萘胺
  参考文献：
  名称：

  2-Amido-8-methoxytetralins: A series of nonindolic melatonin-like agents

  摘要：

  A series of unsubstituted and methoxy-substituted 2-amidotetralins (4a-q) was prepared and evaluated for their ability to compete for 2-[I-125]iodomelatonin binding to chicken retinal membranes and for their potency to inhibit the calcium-dependent release of [H-3]dopamine from rabbit retina. The lead compound, 2-acetamido-8-methoxytetralin (4j), showed a moderate affinity (K(i) = 46 nM) and potency (IC50 = 1.4 nM) at the melatonin receptor. The structural requirements necessary for optimal agonistic activity at the melatonin receptor are as follows. First, the amido group, which should have a small, nonbranched alkyl group, is essential for affinity, and second, the methoxy substituent at the 8-position of the 2-amidotetralin ring is essential for optimal agonistic activity at the melatonin receptor. We concluded that this series of unsubstituted and methoxy-substituted 2-amidotetralins constitutes a class of nonindolic melatonin-like agents that can be used as pharmacological tools to further characterize melatonin receptors and to elucidate the mode of action of melatonin.

  DOI：

  10.1021/jm00072a008

文献信息

• Heterocyclyl-substituted- tetrahydro-napthalen-amine derivatives, their preparation and use as medicaments
  申请人：Laboratorios del Dr. Esteve S.A.

  公开号：EP1975161A1

  公开（公告）日：2008-10-01

  The present invention relates to heterocyclyl-substituted-tetrahydro-naphtalen-amine compounds of general formula (I) methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans or animals, mediated by the 5-HT7 receptor affinity.

  本发明涉及一般式（I）的杂环基取代的四氢萘胺化合物，以及它们的制备方法，包含这些化合物的药物以及它们在制备用于治疗人类或动物的药物中的应用，通过5-HT7受体亲和力介导。
• Combination of a 5-HT7 receptor ligand and an opioid receptor ligand
  申请人：Laboratorios del Dr. Esteve S.A.

  公开号：EP1997493A1

  公开（公告）日：2008-12-03

  The present invention refers to a combination of a 5HT7 receptor ligand and an opioid recptor ligand, especially of a 5HT7 receptor agonist and an opioid recptor agonist, a medicament comprising this combination, or the use of this combination for the treatment of the symptoms of pain, the prevention or the prophylaxis of the symptoms of pain.

  本发明涉及一种5HT7受体配体和阿片受体配体的组合，特别是一种5HT7受体激动剂和阿片受体激动剂，包含该组合的药物，或者利用该组合治疗疼痛症状，预防或预防疼痛症状的用途。
• Heterocyclyl-substituted-tetrahydro-naphthalen derivatives as 5-HT7 receptor ligands
  申请人：Laboratorios del Dr. Esteve S.A.

  公开号：EP1956006A1

  公开（公告）日：2008-08-13

  The present invention relates to heterocyclyl-substituted-tetrahydro-naphthalen compounds of general formula (I) and (Iprot), methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans or animals, mediated by the receptor 5-HT7 affinity.

  本发明涉及一般式（I）和（Iprot）的杂环基取代的四氢萘化合物，其制备方法，包含这些化合物的药物，以及它们用于制备用于治疗人类或动物的药物，通过5-HT7受体亲和力介导。
• Method of Preparing (S)-2-amino-5-Methoxytetralin Hydrochloride
  申请人：HUANG Qingyun

  公开号：US20140046095A1

  公开（公告）日：2014-02-13

  A method of preparing (S)-2-amino-5-methoxytetralin hydrochloride[(S)-2-amino-5-methoxyl-1,2,3,4-tetrahydronaphthalene hydrochloride], comprising the steps of: (1) producing a compound (I) by addition-elimination reaction of 5-methoxy-2-tetralone and R-(+)-a-phenylethylamine; (2) producing a compound (II) by reduction reaction of the compound (I) with a reducing agent; and (3) producing a compound (II) hydrochloride by reacting the compound (II) with a salt-forming agent, then carrying out reduction reaction with a palladium-carbon catalyst to produce (S)-2-amino-5-methoxytetralin hydrochloride. The method can significantly increase the yield of (S)-2-amino-5-methoxytetralin hydrochloride with short synthetic path, low preparation cost and less pollution, which is environmentally friendly and is suitable for medical industrialized production. The structural formulae of the compound (I) and the compound (II) are: resepectively.

  一种制备(S)-2-氨基-5-甲氧基四氢萘盐酸盐[(S)-2-氨基-5-甲氧基-1,2,3,4-四氢萘盐酸盐]的方法，包括以下步骤：(1)通过5-甲氧基-2-四氢萘酮和R-(+)-α-苯乙胺的加成-消除反应制备化合物(I)；(2)通过还原剂对化合物(I)进行还原反应制备化合物(II)；(3)将化合物(II)与盐类生成剂反应，然后使用钯碳催化剂进行还原反应制备化合物(II)盐酸盐。该方法可以显著提高(S)-2-氨基-5-甲氧基四氢萘盐酸盐的产率，具有合成路径短、制备成本低、污染少的特点，环保且适合医药工业化生产。化合物(I)和化合物(II)的结构式如下：（分别列出结构式）。
• Processes for the Preparation of Rotigotine and Intermediates Thereof
  申请人：Apotex Inc.

  公开号：US20170305877A1

  公开（公告）日：2017-10-26

  The present invention provides processes for the preparation of a compound of Formula 2 or a salt thereof, wherein R 1 is selected from the group consisting of H, C 1 -C 3 alkyl, and C(0)R 3 ; R 3 is selected from the group consisting of C 1 -C 6 alkyl, C 6 -C 10 aryl and C 7 -C 20 arylalkyl; the carbon atom marked with “*” is racemic, enantiomerically enriched in the (R)-configuration, or enantiomerically enriched in the (S)-configuration. Also provided are intermediate compounds of the processes.

  本发明提供了制备式2化合物或其盐的方法，其中R1选自H、C1-C3烷基和C(0)R3，R3选自C1-C6烷基、C6-C10芳基和C7-C20芳基烷基；标有“*”的碳原子是外消旋的，富集(R)-构型的对映体或富集(S)-构型的对映体。同时提供了所述方法的中间体化合物。