1-(2-dimethylamino-ethyl)-1H-indol-6-ylamine | 173386-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(2-dimethylamino-ethyl)-1H-indol-6-ylamine
• 英文别名: 6-amino-1-(2-dimethylaminoethyl)-1H-indole；6-amino-1-(2-dimethylaminoethyl)indole；1-[2-(dimethylamino)ethyl]-1H-indol-6-amine；1-[2-(dimethylamino)ethyl]indol-6-amine
• CAS: 173386-74-8
• 化学式: C₁₂H₁₇N₃
• mdl: MFCD11638193
• 分子量: 203.287
• InChiKey: NMLMAJOVSWGCQS-UHFFFAOYSA-N

物化性质

• 沸点：
  368.7±22.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-dimethylamino-ethyl)-1H-indol-6-ylamine 在 盐酸 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 0.17h， 生成 N'-[1-[2-(dimethylamino)ethyl]indol-6-yl]thiophene-2-carboximidamide;hydrochloride
  参考文献：
  名称：

  1,6-Disubstituted indole derivatives as selective human neuronal nitric oxide synthase inhibitors

  摘要：

  A series of 1,6-disubstituted indole derivatives was designed, synthesized and evaluated as inhibitors of human nitric oxide synthase (NOS). By varying the basic amine side chain at the 1-position of the indole ring, several potent and selective inhibitors of human neuronal NOS were identified. In general compounds with bulkier side chains displayed increased selectivity for nNOS over eNOS and iNOS isoforms. One of the compounds, (R)-8 was shown to reduce tactile hyperesthesia (allodynia) after oral administration (30 mg/kg) in an in vivo rat model of dural inflammation relevant to migraine pain. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.042
• 作为产物：
  描述：

  N,N-dimethyl-2-(6-nitro-1H-indol-1-yl)ethan-1-amine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 20.0 ℃ 、137.89 kPa 条件下， 生成 1-(2-dimethylamino-ethyl)-1H-indol-6-ylamine
  参考文献：
  名称：

  药物化学驱动着朝向新型和选择性5-羟色胺5-HT6受体配体的方法。

  摘要：

  基于药物化学指导的假设药效团模型，新系列的吲哚基磺酰胺已被设计和制备为选择性和高亲和性5-羟色胺5-HT（6）受体配体。此外，基于发现库的筛选方法，一系列苯并恶嗪哌啶基磺酰胺被鉴定为选择性5-HT（6）配体。本文中描述的许多化合物具有出色的亲和力，显示的pK（i）值大于8（某些甚至大于9），并且对宽范围（> 50）的其他CNS相关受体具有高选择性。首先，讨论了这些配体的结构亲和性关系。就功能而言，制备了高亲和力的拮抗剂，以及激动剂，甚至部分激动剂。化合物19c和19g代表文献中报道的最高亲和力5-HT（6）激动剂。这些有价值的工具化合物应允许详细研究5-HT（6）受体在相关的动物模型疾病中的作用，例如认知缺陷，抑郁，焦虑或肥胖。

  DOI：

  10.1021/jm049615n

文献信息

• Substituted indole compounds having NOS inhibitory activity
  申请人：Maddaford Shawn

  公开号：US20060258721A1

  公开（公告）日：2006-11-16

  The present invention features inhibitors of nitric oxide synthase (NOS), particularly those that selectively inhibit neuronal nitric oxide synthase (nNOS) in preference to other NOS isoforms. The NOS inhibitors of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing conditions such as, for example, stroke, reperfusion injury, neurodegeneration, head trauma, CABG, migraine headache with and without aura, migraine with allodynia, central post-stroke pain (CPSP), neuropathic pain, morphine/opioid induced tolerance and hyperalgesia.

  本发明涉及一种一氧化氮合酶（NOS）的抑制剂，特别是那些选择性地抑制神经型一氧化氮合酶（nNOS）而不是其他NOS同工酶的抑制剂。本发明的NOS抑制剂，单独或与其他药用活性剂结合使用，可用于治疗或预防诸如中风、再灌注损伤、神经退行性疾病、头部创伤、冠状动脉搭桥术（CABG）、伴或不伴有先兆的偏头痛、伴有疼痛性过敏的偏头痛、中枢性中风后疼痛（CPSP）、神经痛、吗啡/阿片类药物引起的耐受性和过度疼痛等疾病。
• [EN] ACTIVE SUBSTANCE COMBINATION COMPRISING A COMPOUND WITH NPY RECEPTOR AFFINITY AND A COMPOUND WITH 5-HT6 RECEPTOR AFFINITY<br/>[FR] COMBINAISON DE SUBSTANCES ACTIVES COMPORTANT UN COMPOSE A AFFINITE DE RECEPTEUR NPY ET UN COMPOSE A AFFINITE DE RECEPTEUR 5-HT6
  申请人：ESTEVE LABOR DR

  公开号：WO2005014000A1

  公开（公告）日：2005-02-17

  The present invention relates to an active substance combination comprising at least one compound with neuropeptide Y-receptor affinity and at least one compound with 5-HT6 receptor affinity, a medicament comprising said active substance combination, and the use of said active substance combination for the manufacture of a medicament.

  本发明涉及一种活性物质组合，包括至少一种具有神经肽Y受体亲和力的化合物和至少一种具有5-HT6受体亲和力的化合物，以及包含所述活性物质组合的药物和利用该活性物质组合制造药物的用途。
• [EN] INDOL-6 SULFONAMIDE DERIVATIVES, THEIR PREPARATION AND THEIR USE 5-HT-6 AS MODULATORS<br/>[FR] DERIVES D'INDOL-6 SULFONAMIDE, FABRICATION ET UTILISATIONS EN TANT QUE MODULATEURS DE 5-HT-6
  申请人：ESTEVE LABOR DR

  公开号：WO2005013976A1

  公开（公告）日：2005-02-17

  The present invention refers to new sulfonamide derivatives, of general formula (la, lb, lc) optionally in the form of one of their stereoisomers, preferably enantiomers or diastereomers, their racemate, or in the form of a mixture of at least two of their stereoisomers, preferably enantiomers or diastomers, at any mixture ratio or their salts, preferably the corresponding, physiologically acceptable salts, or corresponding solvates; to the process for their preparation, to their application as medicaments in human and/or veterinary therapeutics, and to the pharmaceutical compositions containing them.

  本发明涉及新的磺酰胺衍生物，其一般式为（la、lb、lc），可选地为它们的立体异构体之一，优选为对映异构体或非对映异构体，它们的外消旋体，或者以至少两个它们的立体异构体的混合物的形式存在，优选为对映异构体或非对映异构体，任何混合比例或它们的盐，优选为相应的生理上可接受的盐或相应的溶剂合物；以及它们的制备方法，它们在人类和/或兽医治疗中作为药物的应用，以及包含它们的制药组合物。
• SUBSTITUTED INDOLE COMPOUNDS AND THEIR USE AS 5-HT6 RECEPTOR MODULATORS
  申请人：Merce Vidal Ramon

  公开号：US20070213326A1

  公开（公告）日：2007-09-13

  The present invention relates to substituted indole compound of general formula I, a process for their preparation, medicaments comprising substituted indole compounds as well as the use of substituted indole compounds for the preparation of medicaments, which are suitable e.g. for the prophylaxis and/or treatment of disorders or diseases that are at least partially mediated via 5-HT 6 receptors.

  本发明涉及通式I的取代吲哚化合物、其制备方法、含有取代吲哚化合物的药物以及利用取代吲哚化合物制备药物的用途，其中所述药物适用于预防和/或治疗至少部分通过5-HT6受体介导的紊乱或疾病。
• Active substance combination comprising a compound with npy receptor affinity and a compound with 5-ht6 receptor affinity
  申请人：Torrens Jover Antoni

  公开号：US20070009597A1

  公开（公告）日：2007-01-11

  The present invention relates to an active substance combination comprising at least one compound with neuropeptide Y-receptor affinity, preferably neuropeptide Y5-receptor affinity, and at least one compound with 5-HT 6 receptor affinity, a medicament comprising said active substance combination, and the use of said active substance combination for the manufacture of a medicament.

  本发明涉及一种活性物质组合，包括至少一种具有神经肽Y受体亲和力的化合物，优选为神经肽Y5受体亲和力，以及至少一种具有5-HT6受体亲和力的化合物，一种包含该活性物质组合的药物，以及使用该活性物质组合制造药物。