6,7-dimethoxy-2-aminotetralin | 67445-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6,7-dimethoxy-2-aminotetralin
• 英文别名: 2-Amino-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene；1,2,3,4-tetrahydro-6,7-dimethoxy-2-naphthylamine；2-amino-6,7-dimethoxytetraline；1,2,3,4-tetrahydro-6,7-dimethoxy-2-naphtylamine；2-Amino-6,7-dimethoxytetralin；6,7-Dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 67445-12-9
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: OVSNYLXMTWOUKT-UHFFFAOYSA-N

物化性质

• 沸点：
  330.3±42.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-2-aminotetralin 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl)sulphamide
  参考文献：
  名称：

  新型磺酰胺和磺酰胺结合四氢萘支架作为碳酸酐酶和乙酰胆碱酯酶抑制剂

  摘要：

  氨基、氨甲基四氢萘和苯甲醇与氯磺酰基异氰酸酯 (CSI) 反应得到氨磺酰氨基甲酸酯。氨磺酰氨基甲酸酯通过钯催化的氢解转化为磺酰胺。磺胺是由胺与 MeSO2Cl 反应合成的。用合成的化合物研究了人 (h) 碳酸酐酶 (CA) 同工酶 (hCA I、hCA II) 和乙酰胆碱酯酶 (AChE) 的抑制作用。hCA I 和 hCA II 在低微摩尔或亚微摩尔范围内受到抑制。Ki 值对 hCA I 的范围为 0.91–9.56 µM，对 hCA II 的范围为 3.70–27.88 µM。磺胺类药物 11-13 和磺胺类药物 14-16 对 AChE 具有中等抑制能力。这些发现表明新型磺酰胺 11-13 和磺酰胺 14-16 作为 AChE 和 CA 同工酶抑制剂。

  DOI：

  10.1002/ardp.201300273
• 作为产物：
  描述：

  (3,4-二甲氧基苯基)乙酰氯 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 6,7-dimethoxy-2-aminotetralin
  参考文献：
  名称：

  Facile syntheses of potent dopaminergic agonists and their effects on neurotransmitter release

  摘要：

  The facile syntheses of important intermediates used in the preparation of the two potent dopaminergic argonists, 2-amino-6,7-dihydroxytetrahydronaphthalene (11) (referred to by some authors as ADTN) and its 5,6-dihydroxyl isomer 12, are described. Thus 6,7-dimethyoxy-2-tetralone has been prepared in two steps and 5,6-dimethoxy-2-tetralone in three steps both from commercially available materials. The effects of 11, 12, and the noncatechol analogue, 2-aminotetrahydronaphthalene (ATN), on radioactive neurotransmitter release have been studied in vitro using rat brain slices. It has been shown that both 11 and 12, at a concentraiton of 2 micron, cause a release of [3H]-DA and NA, 11 being more potent than 12 in releasing [3H]-DA. ATN (2 micron) was found to be inactive in these experiments which shows the importance of the catechol function in this uptake--release process.

  DOI：

  10.1021/jm00206a023

文献信息

• Derivatives of 1,2,3,4-tetrahydronaphtylamine endowed with nootropic
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：US05192759A1

  公开（公告）日：1993-03-09

  1,2,3,4-tetrahydronaphthlamines of formula (1) ##STR1## wherein R is H or OCH.sub.3 ; ##STR2## is either at 1 or 2 position R.sub.1 is H; R.sub.2 is selected from: L-prolyl, optionally N-substituted with acetyl or carbobenzoxy, L-pyroglutamyl, (pyrrolidin-2-one-1-yl)acetyl, 3-carboxy-2-hydroxypropyl: or R.sub.1 and R.sub.2 taken together with the nitrogen atom form the ring ##STR3## wherein n=1,2,3 and R.sub.3 -H, OH are nootropic substances potent enhancers of learning processes and memory. Orally or parenterally administrable pharmaceutical compositions in unit dosage form comprise between about 100 and about 500 mg of a compound of formula (1).

  公式（1）中的1,2,3,4-四氢萘胺 ##STR1## 其中R为H或OCH.sub.3; ##STR2## 在1或2位置R.sub.1为H; R.sub.2从以下选取：L-脯氨酰，可选择用乙酰基或苯甲酰基进行N取代，L-吡罗谷氨酰，(吡咯烷-2-酮-1-基)乙酰，3-羧基-2-羟基丙基；或R.sub.1和R.sub.2与氮原子一起形成环 ##STR3## 其中n=1,2,3，R.sub.3 -H，OH为增强学习过程和记忆的智能药物。口服或经肠道给药的单位剂量形式的药物组合物包含约100至约500毫克的公式（1）化合物。
• N-alkyl derivatives of 2-amino-6,7-dimethoxy tetraline and
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：US05047433A1

  公开（公告）日：1991-09-10

  N-alkyl derivatives of 2-amino-6,7-dimethoxy tetraline having general formula (I) ##STR1## wherein R is selected from hydrogen, ethyl, n-propyl and methyl cyclopropyl; R.sub.1 is selected from hydrogen, hydroxy and --OR.sub.3 wherein R.sub.3 is selected from methyl, ethyl and n-propyl; and R.sub.2 is selected from hydrogen, methyl, hydroxy, trifluoromethyl, fluoro and methoxy, are endowed with potent antihypertensive activity.

  2-氨基-6,7-二甲氧基四氢喹啉的N-烷基衍生物具有通式（I）##STR1## 其中R从氢、乙基、正丙基和甲基环丙基中选择；R.sub.1从氢、羟基和-OR.sub.3中选择，其中R.sub.3从甲基、乙基和正丙基中选择；R.sub.2从氢、甲基、羟基、三氟甲基、氟和甲氧基中选择，具有强大的降压活性。
• Derivatives of 2-amino-6,7-dihydroxytetrahydro naphthalene (ADTN)
  申请人：American Hospital Supply Corporation

  公开号：US04314082A1

  公开（公告）日：1982-02-02

  This invention provides derivatives of 2-Amino-6,7-dihydroxy-tetrahydronaphthalene (ADTN) represented by the formula ##STR1## wherein R is OH, alkyloxy, hydroxyalkyl or acyloxy, and R' is an arylalkyl where the aryl group is benzyl, substituted benzyl, phenyl or substituted phenyl and the alkyl group is a straight or branched chain alkyl having one to twenty carbon atoms; and the pharmaceutically acceptable salts thereof. These derivatives of 2-Amino-6,7-dihydroxytetrahydronaphthalene are useful as inotropes.

  本发明提供了2-氨基-6,7-二羟基-四氢萘（ADTN）的衍生物，其化学式为##STR1##其中R为OH，烷氧基，羟基烷基或酰氧基，R'为芳基烷基，其中芳基为苄基，取代苄基，苯基或取代苯基，烷基为一种具有1到20个碳原子的直链或支链烷基;以及其药学上可接受的盐。这些2-氨基-6,7-二羟基四氢萘的衍生物可用作肌力增强剂。
• 2-(N-acyl)amino-6,7-dimethoxy tetralines, and pharmaceutical
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：US05053424A1

  公开（公告）日：1991-10-01

  2-(N-acyl)amino-6,7-dimethoxy tetraline of general formula (I) ##STR1## wherein R is selected from hydrogen and ethyl and A is an aminoacyl or dipeptidyl radical are endowed with potent anti-hypertensive activity.

  通式为（I）的2-（N-酰基）氨基-6,7-二甲氧基四氢萘，其中R选择氢或乙基，A为氨基酰基或二肽基基团，具有强大的抗高血压活性。
• Benz-trisubstituted 2-aminotetralins
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0209275A1

  公开（公告）日：1987-01-21

  The invention relates to compounds of the formula: wherein R1 and R2 are each hydrogen, n-propyl, n-butyl or 4-hydroxyphenetyl; X is hydrogen or halo; and Y is hydrogen or halo provided that one of X and Y is halo and the other is hydrogen. Also disclosed are methods for the preparation of the compounds, pharmaceutical compositions containing them and their activity as dopaminergic receptor antagonists.

  本发明涉及式的化合物： 其中 R1 和 R2 各为氢、正丙基、正丁基或 4-羟基苯乙基； X为氢或卤代；Y为氢或卤代，条件是X和Y中的一个为卤代，另一个为氢。还公开了制备这些化合物的方法、含有这些化合物的药物组合物及其作为多巴胺能受体拮抗剂的活性。