5-羟基-2-N,N-二丙基氨基四氢萘 | 68593-96-4

• 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-羟基-2-N,N-二丙基氨基四氢萘
• 英文名称: (RS)-5-hydroxy-2-(N,N-di-n-propylamino)tetralin
• 英文别名: 5-OH-Dpat；6-(dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-ol
• CAS: 68593-96-4
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: MDBWEQVKJDMEMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 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：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-羟基-2-N,N-二丙基氨基四氢萘 在 三氟化硼乙醚 、 sodium hydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 Di-n-propyl-(6,7,8,9-tetrahydronaphtho[1,2-b]furan-7-yl)-amine
  参考文献：
  名称：

  (Dipropylamino)-tetrahydronaphthofurans: centrally acting serotonin agonists and dopamine agonists-antagonists

  摘要：

  CNS-active aminotetralins containing phenolic moieties were transformed in a simple two-step procedure to the corresponding benzofurans. The compounds were tested in in vitro binding studies at serotonin 5-HT1A and 5-HT2 and dopamine D-2, D-3 and D-4 receptors. These studies revealed that the furan homologs showed overall lower affinities than the phenol counterparts. This was also reflected in vivo in biochemical studies. The benzofuran compounds retained most of the agonist/antagonist activities but with lower potency.

  DOI：

  10.1016/s0960-894x(97)10068-3
• 作为产物：
  描述：

  (S)-(-)-5-methoxy-2-N,N-dipropylaminotetralin 以61%的产率得到
  参考文献：
  名称：

  MCDERMED J. D.; MCKENZIE G. M.; FREEMAN H. S., J. MED. CHEM. , 1976, 19, NO 4, 547-549

  摘要：

  DOI：

文献信息

• Derivatives of 2-aminotetralins and pharmaceutical analogs thereof exhibiting differentail cns receptor activity and behavior
  申请人：——

  公开号：US20030225154A1

  公开（公告）日：2003-12-04

  Aminotetralin derivatives and pharmacological analogs thereof which contain an N-propynyl group exhibit differential dopaminergenic receptor activity. The subject compounds are useful in affecting dopamine receptor activity, particularly in exhibiting differing activity among the various dopamine receptor subtypes. The compounds are useful in treating CNS disorders in mammals in general, and humans in particular.

  含有N-丙炔基的氨基四氢萘衍生物及其药理类似物表现出不同的多巴胺受体活性。这些化合物在影响多巴胺受体活性方面很有用，尤其是在不同多巴胺受体亚型之间表现出不同活性方面。这些化合物在一般哺乳动物，特别是人类中治疗中枢神经系统疾病方面很有用。
• Subcutaneous Delivery of Poly(oxazoline) Polymer Conjugates
  申请人：SERINA THERAPEUTICS, INC.

  公开号：US20160303250A1

  公开（公告）日：2016-10-20

  The present disclosure provides polymer conjugates comprising a polymer and an agent, the agent linked to the polymer via a linking group containing a hydrolyzable moiety.

  本公开提供了聚合物共轭物，包括聚合物和一个药物，该药物通过含有可水解基团的连接基团与聚合物相连。
• Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[(trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo
  作者：Clas Sonesson、Maria Boije、Kjell Svensson、Agneta Ekman、Arvid Carlsson、Arthur G. Romero、Iain J. Martin、J. Neil Duncan、Laurence J. King、Hakan Wikstrom

  DOI：10.1021/jm00074a022

  日期：1993.10

  potent than their phenolic analogs. The absolute oral bioavailability of compound 8 (8-triflate) was 4-5 times greater than the corresponding hydroxylated compound. Interestingly, in the in vivo biochemical assay compound 8 was found to be more potent after oral than after subcutaneous administration, indicating formation of one or more active metabolites. Following a study of the metabolism of compound

  5-，6-，7-和8-羟基化的2-（二-正丙基氨基）-teralins 1-4的外消旋三氟甲磺酸衍生物5-8在体外具有与其酚类对应物相似的药理特性大鼠体内的结合和体内生化与行为测定。因此，皮下注射5-，6-和7-三氟甲磺酸盐显示出实质上的多巴胺能激动剂特性，而8-三氟甲磺酸盐被证明是选择性的5-HT1A受体激动剂。关于它们的激动剂活性，三氟甲磺酸酯的效力低于其酚类类似物。化合物8（8-三氟甲磺酸盐）的绝对口服生物利用度是相应羟基化化合物的4-5倍。有趣的是，在体内生化分析中，发现化合物8口服后比皮下给药更有效，表明形成一种或多种活性代谢产物。在研究了大鼠肝细胞中化合物8的代谢后，单丙基类似物9被确定为主要代谢产物，令人惊讶地发现它比化合物8更有效。口服给予化合物5（5-三氟甲磺酸酯）会导致行为和生化反应皮下给药后未见混合DA / 5-HT1A激动剂特性的影响。这些结果也可以指示活性代谢物的
• 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。
• Hybrid 2-aminoterailin and aryl-substituted piperazine compounds and their use in altering CNS activity
  申请人：Dutta K. Aloke

  公开号：US20060020132A1

  公开（公告）日：2006-01-26

  Hybrid compounds containing an aminotetralin moiety or a heterocyclic and/or open chain analog thereof linked through an alkylene group to an aryl ring system-substituted piperidiene moiety exhibit high levels of CNS activity, in some cases exhibiting especially high relative binding efficiencies between D3 and D2 dopaminergic receptor subtypes.

  含有氨基四氢萘基团或杂环和/或开链类似物的混合化合物，通过烷基链连接到芳香环系统取代的哌啶基团，表现出高水平的中枢神经系统活性，在某些情况下表现出D3和D2多巴胺受体亚型之间特别高的相对结合效率。