2-(二-n-丙氨基)-5,6-二羟基四氢萘 | 64309-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 2-(二-n-丙氨基)-5,6-二羟基四氢萘
• 英文名称: 5,6-dihydroxy-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene
• 英文别名: 5,6-dihydroxy-2-(di-n-propylamino)tetralin；(+/-)-5,6-dihydroxy-DPAT；2 (dipropylamino) 1,2,3,4 tetrahydronaphthalene 5,6 diol；6-(Dipropylamino)-5,6,7,8-tetrahydronaphthalene-1,2-diol
• CAS: 64309-39-3
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: JQHSYAQISCFWOK-UHFFFAOYSA-N

物化性质

• 沸点：
  413.8±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922299090

反应信息

• 作为产物：
  描述：

  1,2,6-三甲氧基萘 在 乙醇 、 氢碘酸 、 sodium 、 乙酸酐 作用下， 生成 2-(二-n-丙氨基)-5,6-二羟基四氢萘
  参考文献：
  名称：

  Synthesis and pharmacology of some 2-aminotetralins. Dopamine receptor agonists

  摘要：

  A series of 2-amino-1,2,3,4-tetrahydronaphthalene compounds bearing substituents on the nitrogen and in the aromatic ring was synthesized from beta-tetralone intermediates. Compounds were screened in vivo for dopaminergic activity using tests in which apomorphine was especially active. It was found that apparent dopaminergic activity is inherent in 2-dialkylaminotetralins, the dipropylamine substitution being the most consistently productive amine group studies. Activity was greatly enhanced by proper substitution in the aromatic ring. The 5,6-dihydroxy group was the best potentiating group found. These data support the idea that the extended conformation for the phenylethylamine moiety of ampmorphine and dopamine is favorable for dopaminergic agonist activity. They also suggest that an unetherified catechol group may not be essential for such activity.

  DOI：

  10.1021/jm00238a008

文献信息

• [EN] A PROCESS FOR THE MANUFACTURE OF (2S,3S,4S,5R,6S)-3,4,5-TRIHYDROXY-6-(((4AR,10AR)-7-HYDROXY-1-PROPYL-1,2,3,4,4A,5,10,10A-OCTAHYDROBENZO[G]QUINOLIN-6-YL)OXY)TETRAHYDRO-2H-PYRAN-2-CARBOXYLIC ACID AND INTERMEDIATE THEREOF<br/>[FR] PROCÉDÉ DE FABRICATION DE (2S,3S,4S,5R,6S) -3,4,5-TRIHYDROXY-6-(((4AR,10AR)-HYDROXY-1-PROPYL-1,2,3,4,4 A,5,10,10A-OCTAHYDROBENZO[G]QUINOLIN-6-YL)OXY)TÉTRAHYDRO-2H-PYRAN-2-CARBOXYLIQUE ET UN INTERMÉDIAIRE DE CELUI-CI
  申请人：H LUNDBECK AS

  公开号：WO2020234270A1

  公开（公告）日：2020-11-26

  The present invention relates to a process for manufacturing (2S,3S,4S,5R,6S)-3,4,5- trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a- octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid with the formula (Id) below and pharmaceutically acceptable salts thereof. The compound of formula (Id) is a prodrug of a catecholamine for use in treatment of neurodegenerative diseases and disorders such as Parkinson's Disease. The invention also relates to a new intermediate of said process.

  本发明涉及一种制造(2S,3S,4S,5R,6S)-3,4,5-三羟基-6-(((4aR,10aR)-7-羟基-1-丙基-1,2,3,4,4a,5,10,10a-辛氢苯并[g]喹啉-6-基)氧基)四氢-2H-吡喃-2-羧酸（化学式见下文）及其药用盐的过程。化学式（Id）的化合物是一种儿茶酚胺的前药，用于治疗神经退行性疾病和帕金森病等疾病。该发明还涉及该过程的新中间体。
• 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。
• [EN] METHOD FOR TREATING PARKINSON'S DISEASE BY ADMINISTERING (-)-5-KETO-2-N,N-DI-N-PROPYLAMINO-TETRAHYDROTETRALIN<br/>[FR] PROCEDE DE TRAITEMENT DE LA MALADIE DE PARKINSON PAR ADMINISTRATION DE (-)-5-CETO-2-N,N-DI-N-PROPYLAMINO-TETRAHYDROTETRALINE
  申请人：WARNER LAMBERT CO

  公开号：WO2001028977A1

  公开（公告）日：2001-04-26

  Parkinson's disease is treated with a compound of Formula (I) or a pharmaceutically acceptable salt thereof.

  帕金森病可以用公式（I）的化合物或其药学上可接受的盐来治疗。
• 5-HYDROXYMETHYL-2-AMINOTETRALINS AS CARDIOVASCULAR AGENTS
  申请人：ZAMBON GROUP S.p.A.

  公开号：EP0970042A1

  公开（公告）日：2000-01-12
• ENDODONTIC POST SYSTEM
  申请人：APOTEX INC.

  公开号：US20160297745A1

  公开（公告）日：2016-10-13

  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.