2-benzylamino-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene | 66996-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-benzylamino-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene
• 英文别名: N-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 66996-58-5
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: TUZOWFPSCLQYFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 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：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzylamino-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene 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
• 作为产物：
  描述：

  (3,4-二甲氧基苯基)乙酰氯 生成 2-benzylamino-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene
  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

• Aminotetralin derivatives
  申请人：Dr. Karl Thomae GmbH

  公开号：US04584293A1

  公开（公告）日：1986-04-22

  This invention related to new aminotetralin derivatives of formula I ##STR1## wherein ##STR2## B is methylene or, when A is --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --NH--CO-- or --CH.sub.2 --CO--, B can also be carbonyl or thiocarbonyl; E is a C.sub.2 -C.sub.4 straight-chain alkylene, optionally substituted by a C.sub.1 -C.sub.3 alkyl, or is 2-hydroxy-n-propylene, 2-hydroxy-n-butylene or 3-hydroxy-n-butylene; R.sub.1 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, nitro, amino, C.sub.1 -C.sub.3 alkylamino, C.sub.1 -C.sub.3 dialkylamino, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkylthio, hydroxy, C.sub.1 -C.sub.3 alkoxy or phenyl C.sub.1 -C.sub.3 alkoxy; R.sub.2 is hydrogen, chlorine, bromine, hydroxy, C.sub.1 -C.sub.3 alkoxy phenyl C.sub.1 -C.sub.3 alkoxy, or C.sub.1 -C.sub.3 alkyl or, together with R.sub.1, can be a C.sub.1 -C.sub.2 alkylenedioxy; R.sub.3 and R.sub.4 are each independently selected from hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.3 alkyl, hydroxy, C.sub.1 -C.sub.3 alkoxy, nitro, amino, C.sub.1 -C.sub.3 alkylamino, or C.sub.1 -C.sub.3 dialkylamino, or together can be methylenedioxy; and R.sub.5 is hydrogen, C.sub.3 -C.sub.5 alkenyl, C.sub.1 -C.sub.3 alkyl, or phenyl C.sub.1 -C.sub.3 alkyl, and nontoxic, pharmaceutically acceptable addition salts thereof which have valuable pharmacological properties, particularly a long-lasting heart rate lowering effect and the effect of reducing the O.sub.2 requirement of the heart.

  这项发明涉及公式I的新的氨基四氢萘衍生物，其中B是亚甲基，当A是--CH.sub.2--CH.sub.2--时，B也可以是羰基或硫代羰基；E是一种C.sub.2-C.sub.4直链烷基，可以选择性地被C.sub.1-C.sub.3烷基取代，或者是2-羟基-n-丙烷基，2-羟基-n-丁烷基或3-羟基-n-丁烷基；R.sub.1是氢、氟、氯、溴、三氟甲基、硝基、氨基、C.sub.1-C.sub.3烷基氨基、C.sub.1-C.sub.3二烷基氨基、C.sub.1-C.sub.3烷基、C.sub.1-C.sub.3烷基硫、羟基、C.sub.1-C.sub.3烷氧基或苯基C.sub.1-C.sub.3烷氧基；R.sub.2是氢、氯、溴、羟基、C.sub.1-C.sub.3烷氧基苯基C.sub.1-C.sub.3烷氧基、或C.sub.1-C.sub.3烷基或者与R.sub.1一起可以是C.sub.1-C.sub.2烷二氧基；R.sub.3和R.sub.4各自独立地选自氢、氟、氯、溴、C.sub.1-C.sub.3烷基、羟基、C.sub.1-C.sub.3烷氧基、硝基、氨基、C.sub.1-C.sub.3烷基氨基或C.sub.1-C.sub.3二烷基氨基，或者一起可以是亚甲基二氧基；R.sub.5是氢、C.sub.3-C.sub.5烯丙基、C.sub.1-C.sub.3烷基或苯基C.sub.1-C.sub.3烷基，以及其无毒的、药学上可接受的盐，具有有价值的药理学特性，特别是长效降低心率和减少心脏对O.sub.2需求的作用。
• REIFFEN, M.;HEIDER, J.;AUSTEL, V.;HAUEL, N.;KOBINGER, W.;LILLIE, C.
  作者：REIFFEN, M.、HEIDER, J.、AUSTEL, V.、HAUEL, N.、KOBINGER, W.、LILLIE, C.

  DOI：——

  日期：——
• BETA-2 SELECTIVE ADRENERGIC RECEPTOR AGONISTS
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20200360304A1

  公开（公告）日：2020-11-19

  Aspects of the present disclosure include conformationally restricted analogs of catecholamine type compounds (e.g., isoprenaline, adrenaline, noradrenaline) which activate β2AR with high selectivity over β1AR. The subject beta-2 selective adrenergic receptor agonist compounds may serve as bronchiodilators and find use in the treatment of a variety of bronchoconstrictive diseases and conditions. Also provided are compositions and methods for treating preterm labor. A method of treating acute asthma including administration of a subject compound to a subject in need thereof is provided. The subject method can provide for reduced undesirable side effects associated with non-selective β-adrenergic receptor agonism, such as inotropic and chronotropic effects that leads to elevated blood pressure. The compounds can also be used to prevent or treat heart failure. Kits and compositions for practicing the subject methods are also provided.
• US4584293A
  申请人：——

  公开号：US4584293A

  公开（公告）日：1986-04-22
• [EN] BETA-2 SELECTIVE ADRENERGIC RECEPTOR AGONISTS<br/>[FR] AGONISTES DE RÉCEPTEUR ADRÉNERGIQUE BÊTA-2 SÉLECTIF
  申请人：UNIV LELAND STANFORD JUNIOR

  公开号：WO2019112913A1

  公开（公告）日：2019-06-13

  Aspects of the present disclosure include conformationally restricted analogs of catecholamine type compounds (e.g., isoprenaline, adrenaline, noradrenaline) which activate β2AR with high selectivity over β1AR. The subject beta-2 selective adrenergic receptor agonist compounds may serve as bronchiodilators and find use in the treatment of a variety of bronchoconstrictive diseases and conditions. Also provided are compositions and methods for treating preterm labor. A method of treating acute asthma including administration of a subject compound to a subject in need thereof is provided. The subject method can provide for reduced undesirable side effects associated with non-selective β-adrenergic receptor agonism, such as inotropic and chronotropic effects that leads to elevated blood pressure. The compounds can also be used to prevent or treat heart failure. Kits and compositions for practicing the subject methods are also provided.