2-(5-甲氧基-2-甲基-1H-吲哚-3-基)-N,N-二甲基乙胺 | 67292-68-6

• 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
• 中文名称: 2-(5-甲氧基-2-甲基-1H-吲哚-3-基)-N,N-二甲基乙胺
• 英文名称: [2-(5-methoxy-2-methyl-indol-3-yl)-ethyl]-dimethyl-amine
• 英文别名: [2-(5-Methoxy-2-methyl-indol-3-yl)-aethyl]-dimethyl-amin；N,N-dimethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)ethylamine；N,N-dimethyl-2-(5-methoxy-2-methylindol-3-yl)ethylamine；2-methyl-5-methoxy-N,N-dimethyltryptamine；Indole, 3-(2-(dimethylamino)ethyl)-5-methoxy-2-methyl-；2-(5-methoxy-2-methyl-1H-indol-3-yl)-N,N-dimethylethanamine
• CAS: 67292-68-6
• 化学式: C₁₄H₂₀N₂O
• 分子量: 232.326
• InChiKey: ACEHBQPPDDGCGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  374.49°C (rough estimate)
• 密度：
  1.0151 (rough estimate)
• 溶解度：
  DMF：30 mg/ml； DMSO：30 mg/ml；乙醇：30 mg/ml；乙醇:PBS (pH 7.2) (1:1): 0.5 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-甲氧基-2-甲基-1H-吲哚-3-基)-N,N-二甲基乙胺 在 盐酸 、 正丁基锂 、 N2 、 CO₂ 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2-ethyl-5-methoxy-N,N-dimethyltryptamine maleate
  参考文献：
  名称：

  Selective 5-HT6 receptor ligands

  摘要：

  已经确定了对5-HT6受体具有增强亲和力和选择性的化合物。这些化合物可以通过以药理学上可接受的途径向需要治疗的患者进行给药，在治疗精神障碍方面发挥治疗作用，或者可以通过众所周知的筛选方法识别5-HT6受体的拮抗剂，这些拮抗剂本身可以用于治疗精神障碍。

  公开号：

  US06403808B1
• 作为产物：
  描述：

  2-(5-Methoxy-2-methyl-1H-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide 在 lithium aluminium tetrahydride 作用下， 生成 2-(5-甲氧基-2-甲基-1H-吲哚-3-基)-N,N-二甲基乙胺
  参考文献：
  名称：

  Characterization of the 5-HT₇ Receptor. Determination of the Pharmacophore for 5-HT₇ Receptor Agonism and CoMFA-Based Modeling of the Agonist Binding Site

  摘要：

  On the basis of a set of 20 diverse 5-HT7 receptor agonists, the pharmacophore for 5-HT7 receptor agonism was determined. Additionally two CoMFA models were developed, based on different alignments of the agonists. Both models show good correlations between experimental and predictive pK(i) values and show a high degree of similarity. The CoMFA fields were subsequently used to map the agonist binding site of the model of the 5-HT7 receptor. Important roles in ligand binding are attributed to Asp162 of TM3 (interaction with a protonated nitrogen), and Thr244 of TM5 (interaction with a substituent at an aromatic moiety). Amino acid residues of the aromatic cluster of TM6 are hypothesized to play an important role in ligand binding as pi-pi stacking moieties. Agonists missing a hydrogen-bond-accepting moiety, but possessing an aromatic substituent instead, seem to bind the receptor with high affinity as well by occupying a lipophilic pocket hosted by residues of TM5 and TM6.

  DOI：

  10.1021/jm030826m

文献信息

• 2-Substituted Tryptamines:  Agents with Selectivity for 5-HT₆ Serotonin Receptors
  作者：Richard A. Glennon、Mase Lee、Jagadeesh B. Rangisetty、Malgorzata Dukat、Bryan L. Roth、Jason E. Savage、Ace McBride、Laura Rauser、Sandy Hufeisen、David K. H. Lee

  DOI：10.1021/jm990550b

  日期：2000.3.1

  5-HT(6) serotonin agonists. It was found that 5-HT(6) receptors accommodate small alkyl substituents at the indole 2-position and that the resulting compounds can bind with affinities comparable to that of serotonin. In particular, 2-ethyl-5-methoxy-N, N-dimethyltryptamine (8) binds with high affinity at human 5-HT(6) receptors (K(i) = 16 nM) relative to 5-HT (K(i) = 75 nM) and was a full agonist, at least

  几种2-烷基-5-甲氧基色胺类似物被设计和制备为潜在的5-HT（6）5-羟色胺激动剂。发现5-HT（6）受体在吲哚2位上容纳小的烷基取代基，并且所产生的化合物可以结合具有与血清素相当的亲和力。特别是，相对于5-HT（K（i），2-乙基-5-甲氧基-N，N-二甲基色胺（8）以高亲和力结合人5-HT（6）受体（K（i）= 16 nM） ）= 75 nM），并且在激活腺苷酸环化酶方面至少是与血清素（K（act）= 5.0 nM）一样有效的激动剂（8：K（act）= 3.6 nM）。化合物8对其他几个5-HT受体群体表现出适度的亲和力，尤其是h5-HT（1A）（K（i）= 170 nM），h5-HT（1D）（K（i）= 290 nM）和h5 -HT（7）（K（i）= 300 nM）受体，但否则具有选择性。化合物8代表迄今为止报道的第一个也是最具选择性的5-HT（6）激动剂。用苯基取代2-乙基取代基
• [EN] PREPARATION OF 3-AMINOALKYL-SUBSTITUTED INDOLE DERIVATIVES FROM PHENYLHYDRAZINES AND AMINOKETONES<br/>[FR] PREPARATION DE DERIVES D'INDOLE A SUBSTITUTION 3-AMINOALKYLE A PARTIR DE PHENYLHYDRAZINES ET D'AMINOCETONES
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2004041781A1

  公开（公告）日：2004-05-21

  The present invention relates to a process for the preparation of indole derivatives, particularly those, which are useful as pharmaceutical intermediates. The process involves formation of hydrazone derivative between a phenyl hydrazine and a ketone amine, followed by cyclisation to give desired 2,3-substituted indole derivative in the presence of acid catalyst.

  本发明涉及一种制备吲哚衍生物的方法，特别是那些作为药物中间体有用的衍生物。该方法涉及在酸催化剂存在下，通过苯基肼和酮胺之间的缩醛衍生物的形成，然后进行环化反应，得到所需的2,3-取代吲哚衍生物。
• Indole and indoline derivatives as 5-HT6 selective ligands
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US06187805B1

  公开（公告）日：2001-02-13

  Three classes of indole and indoline derivatives are disclosed as ligands selective for the 5-HT6 receptors, and hence of value in the treatment or prevention of CNS disorders, including Alzheimer's disease, Parkinson's disease, schizophrenia, depression and anxiety. A particular class, 1-substituted-4-(&ohgr;-N,N-dialkyl-aminoalkyl)indoles, are claimed as novel compounds.

  揭示了三类吲哚和吲哚啉衍生物作为选择性结合到5-HT6受体的配体，因此在治疗或预防中枢神经系统疾病方面具有价值，包括阿尔茨海默病、帕金森病、精神分裂症、抑郁症和焦虑症。其中一类称为1-取代-4-(&ohgr;-N,N-二烷基氨基烷基)吲哚，被称为新型化合物。
• Selective 5-HT 6 receptor ligands
  申请人：VIRGINIA COMMONWEALTH UNIVERSITY

  公开号：EP1693366A1

  公开（公告）日：2006-08-23

  Compounds which have enhanced affinity and selectivity for 5-HT6 receptors have been identified. These compounds can be used therapeutically in the treatment of mental disorders via administration in a pharmacologically acceptable delivery route to a patient in need thereof, or can be used to identify antagonists of 5-HT6 receptors by well known screening methodologies which could themselves be used in the treatment of mental disorders.

  已鉴定出对 5-HT6 受体具有更强亲和力和选择性的化合物。这些化合物可以通过药理学上可接受的给药途径用于治疗精神障碍，也可以通过众所周知的筛选方法确定 5-HT6 受体的拮抗剂，这些拮抗剂本身也可用于治疗精神障碍。
• N-(2-arylethyl) benzylamines as antagonists of the 5-ht6 receptor
  申请人：——

  公开号：US20040132800A1

  公开（公告）日：2004-07-08

  The present invention provides compounds of formula (I), which are antagonists of the 5-HT 6 receptor. 1

  本发明提供的式 (I) 化合物是 5-HT 6 受体的拮抗剂。