(2R)-1,2,3,4-四氢-5-甲氧基-N-丙基-2-萘胺 | 101403-25-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: (2R)-1,2,3,4-四氢-5-甲氧基-N-丙基-2-萘胺
• 英文名称: (R)-5-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine
• 英文别名: (R)-5-methoxy-2-(N-n-propylamino)tetralin；(R)-5-methoxy-N-propyl-2-aminotetraline；((R)-5-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine hydrochloride；(2R)-5-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 101403-25-2
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: ICJPCRXVYMMSJY-GFCCVEGCSA-N

物化性质

• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-1,2,3,4-四氢-5-甲氧基-N-丙基-2-萘胺 在 盐酸 、 水 、 氢溴酸 、 sodium carbonate 、 potassium carbonate 、 sodium hydrogensulfite 、 溶剂黄146 、 十二硫醇 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 邻二甲苯 、 methyltretrahydrofuran, 2- 、 水 、 乙酸乙酯 为溶剂， 反应 2.91h， 生成 盐酸罗替戈汀
  参考文献：
  名称：

  [EN] PROCESSES FOR THE RESOLUTION OF NITROGEN SUBSTITUTED (S) - 5 -ALKOXY- 2 -AMINOTETRALIN DERIVATIVES
  [FR] NOUVEAU PROCÉDÉ POUR LA PRÉPARATION DE DÉRIVÉS D'AMINOTÉTRALINES SUBSTITUÉS SUR L'AZOTE

  摘要：

  公开号：

  WO2011161255A4
• 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， 反应 3.0h， 生成 (2R)-1,2,3,4-四氢-5-甲氧基-N-丙基-2-萘胺
  参考文献：
  名称：

  Fluorescent probes for dopamine receptors: synthesis and characterization of fluorescein and 7-nitrobenz-2-oxa-1,3-diazol-4-yl conjugates of D-1 and D-2 receptor ligands

  摘要：

  Fluorescent probes have been designed and developed for dopamine D-1 and D-2 receptors. Fluorescein and/or NBD (7-nitrobenz-2-oxa-1,3-diazol-4-yl) derivatives of PPHT (D-2 agonist), spiperone (D-2 antagonist), SKF 38393 (D-1 agonist), and SKF 83566 (D-1 antagonist) were synthesized via their amino-functionalized analogues and all ligands were pharmacologically evaluated by measuring their ability to displace [H-3]SCH 23390 and [H-3]spiperone from D-1 and D-2 receptor sites in caudate putamen of monkeys (Macaca fascicularis). The fluorescein derivatives of PPHT and SKF 83566 and the NBD derivatives of spiperone and SKF 83566 retained the high affinity and selectivity of the parent ligands. The NBD derivatives of PPHT showed higher D-2 receptor affinity and selectivity than their parent ligands. The enantiomers of the fluorescent derivatives of PPHT were also synthesized and were found to exhibit stereoselectivity in binding to the D-2 receptor, with the S enantiomers having a considerably higher affinity than their R analogues. In contrast to these results, the fluorescein derivative of SKF 38393 showed only a low affinity for the D-1 receptor. These fluorescein- and NBD-coupled D-1 and D-2 receptor ligands have considerable significance as potential probes in the study of distribution of the receptors at the cellular/subcellular level and of their mobility in membranes in normal/diseased states by use of fluorescence microscopic and fluorescence photobleaching recovery techniques, respectively. The development of these novel fluorescent probes should also provide new leads for the design and synthesis of additional fluorescent ligands with better fluorescent properties and/or higher affinity/selectivity for the DA receptors.

  DOI：

  10.1021/jm00115a012

文献信息

• Further Structure–Activity Relationships Study of Hybrid 7-{[2-(4-Phenylpiperazin-1-yl)ethyl]propylamino}-5,6,7,8-tetrahydronaphthalen-2-ol Analogues: Identification of a High-Affinity D3-Preferring Agonist with Potent in Vivo Activity with Long Duration of Action
  作者：Swati Biswas、Suhong Zhang、Fernando Fernandez、Balaram Ghosh、Juan Zhen、Eldo Kuzhikandathil、Maarten E. A. Reith、Aloke K. Dutta

  DOI：10.1021/jm070860r

  日期：2008.1.1

  (+)-isomeric counterpart. Binding results indicated highest selectivity for D3 receptors in compound (-)- 10 ( K i = 0.35 nM; D2/D3 = 71). In the 5-hydroxy series, highest selectivity for D3 receptors was exhibited by compound (-)- 25 ( K i = 0.82 nM; D2/D3 = 31.5). Most potent compounds exhibited binding and functional affinities at the sub-nanomolar level for the D3 receptor. Binding assays were carried

  本文介绍了一种针对多巴胺D2 / D3受体的氨基四氢萘-哌嗪类杂合分子的扩展结构-活性关系研究。已经开发出各种类似的作为位置异构体的类似物，其中酚羟基在芳族环上的位置已经改变。在两个邻苯二酚衍生物之间，具有两个亚甲基接头长度的化合物6e相对于具有四个亚甲基接头的化合物6f对D3的表现出更高的亲和力和对D3的选择性（6e和6f分别为D2 / D3 = 50.6 vs 7.51）。通常，（-）-异构体比（+）-异构体更有效。结合结果表明对化合物（-）-10中的D3受体具有最高选择性（K i = 0.35 nM； D2 / D3 = 71）。在5-羟基系列中，化合物（-）-25（K i = 0.）对D3受体的选择性最高。82 nM；D2 / D3 = 31.5）。大多数有效的化合物在亚纳摩尔水平上对D3受体表现出结合和功能亲和力。用tri化的烯酮作为放​​射性配体，用表达D2或D3受体的HEK-
• Resolved monophenolic 2-aminotetralins and 1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolines: structural and stereochemical considerations for centrally acting pre- and postsynaptic dopamine-receptor agonists
  作者：Haakan Wikstroem、Bengt Andersson、Domingo Sanchez、Per Lindberg、Lars Erik Arvidsson、Anette M. Johansson、J. Lars G. Nilsson、Kjell Svensson、Stephan Hjorth、Arvid Carlsson

  DOI：10.1021/jm00380a012

  日期：1985.2

  centrally acting dopamine (DA) agonists acting on both pre- and postsynaptic DA receptors. The compounds resolved are 5- and 7-hydroxy-2-(di-n-propylamino)tetralin and cis- and trans-7-hydroxy-4-n-propyl-1,2,3,4,4a,5,6,10b-octahydrobenzo [f]quinoline. By the superimposition of the structures of the more active enantiomers of these compounds with those of known dopaminergic agonists, apomorphine and ergolines

  揭示了作用在突触前和突触后DA受体上的中枢作用多巴胺（DA）激动剂的详细结构-活性关系。解析出的化合物为5-和7-羟基-2-（二-正丙基氨基）四氢萘林和顺-和反7-羟基-4-正丙基-1,2,3,4,4a，5,6 ，10b-八氢苯并[f]喹啉。通过将这些化合物的更具活性的对映异构体的结构与已知的多巴胺能激动剂，阿扑吗啡和麦角灵重叠，可以提出一种新的DA受体模型，作为当前DA受体理论的产物。该受体模型最重要的概念之一是强调多巴胺能化合物的N取代基可能占据的位置。这些位置中的一个在空间上定义得很好，而另一个方向在空间上不太重要。该模型已被用来解释某些先前报道的结构缺乏多巴胺能活性，还用于预测新型结构的特性，包括固有手性，该结构应对DA受体具有活性。希望这种启发式DA受体模型将导致发现更多选择性和有效药理学工具，最终可能导致开发用于治疗中枢神经系统多巴胺能功能疾病的治疗剂。
• Novel Process for the Preparation of Nitrogen Substituted Aminotetralins Derivatives
  申请人：Ates Celal

  公开号：US20130102794A1

  公开（公告）日：2013-04-25

  The present invention provides an alternative synthesis of N-substituted aminotetralines comprising resolution of N-substituted aminotetralins of formula (II), wherein R 1 , R 2 and R 3 are as defined for compound of formula (I).

  本发明提供了一种N-取代氨基四氢萘的替代合成方法，包括对式（II）的N-取代氨基四氢萘进行分离，其中R1、R2和R3如式（I）化合物所定义。
• Investigation of various N-heterocyclic substituted piperazine versions of 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-ol: Effect on affinity and selectivity for dopamine D3 receptor
  作者：Dennis A. Brown、Manoj Mishra、Suhong Zhang、Swati Biswas、Ingrid Parrington、Tamara Antonio、Maarten E.A. Reith、Aloke K. Dutta

  DOI：10.1016/j.bmc.2009.04.031

  日期：2009.6

  displaying higher affinity at both D2 and D3 receptors compared to its enantiomer (+)-10e (Ki; D2 = 113 nM, D3 = 3.73 nM). Additionally, compound (−)-10e was more potent and selective for the D3 receptor compared to either 7-OH-DPAT or 5-OH-DPAT. Among the bioisosteric derivatives, the indazole derivative 10g and benzo[b]thiophene derivative 10i exhibited the highest affinity for D2 and D3 receptors. In the

  在这里，我们报告了属于 5/7-[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8 的几种杂环类似物的设计和合成-tetrahydro-naphthalen-2-ol 系列分子。对化合物进行 [ 3 H] 螺环哌啶酮结合测定，用表达 D2 或 D3 多巴胺受体的 HEK-293 细胞进行，以评估它们的抑制常数 ( K i) 在这些受体上。结果表明哌嗪环上的 N-取代可以容纳各种取代的吲哚环。结果还表明，为了保持对 D3 受体的高亲和力和选择性，杂环不需要直接连接到哌嗪环上，因为此处包括的大多数化合物通过酰胺或亚甲基接头连接到杂环部分。最有效的外消旋化合物10e的对映异构体与 (-)- 10e ( K i ; D2 = 47.5 nM, D3 = 0.57 nM)表现出不同的活性，与其对映异构体 (+)- 10e相比，对 D2 和
• Synthesis of Pharmaceutically Relevant 2‐Aminotetralin and 3‐Aminochroman Derivatives via Enzymatic Reductive Amination
  作者：Joan Citoler、Vanessa Harawa、James R. Marshall、Han Bevinakatti、James D. Finnigan、Simon J. Charnock、Nicholas J. Turner

  DOI：10.1002/anie.202110321

  日期：2021.11.8

  The biocatalytic synthesis of pharmaceutically relevant 2-aminotetralin and 3-aminochroman derivatives was achieved with imine reductases (IREDs) at preparative scale, showing enantiocomplementary selectivity for most of the products and yields as high as 91 %. Precursors of Ebalzotan, Robalzotan, Alnespirone and 5-OH-DPAT were successfully synthesised, as well as the Parkinson's disease agent Rotigotine

  药学相关的 2-氨基四氢萘和 3-氨基色满衍生物的生物催化合成是使用亚胺还原酶 (IRED) 在制备规模上实现的，对大多数产品显示出对映互补选择性，产率高达 91%。Ebalzotan、Robalzotan、Alnespirone 和 5-OH-DPAT 的前体以及帕金森病药物罗替高汀的前体均通过 3 步化学酶促方法成功合成。