5-methoxy-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1Hindole | 109793-69-3

• 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: 5-methoxy-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1Hindole
• 英文别名: 5-Methoxy-2-methyl-3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indole；5-methoxy-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole
• CAS: 109793-69-3
• 化学式: C₁₅H₁₈N₂O
• 分子量: 242.321
• InChiKey: ZQZWLJUKYOXRPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-哌啶酮 、 5-甲氧基-2-甲基吲哚 在 磷酸 、 溶剂黄146 作用下， 生成 5-methoxy-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1Hindole
  参考文献：
  名称：

  2-Alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles as novel 5-HT6 receptor agonists

  摘要：

  A series of 2-alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles were synthesized and evaluated for their 5-HT6 activity. The most potent agonist in this series was 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole with an IC50 = 7.4 nM in H-3-LSD binding and an EC50 = 1.0 nM in a functional assay measuring production of cyclic AMP. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.067

文献信息

• Structure–activity relationship of 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole analogues as 5-HT6 receptor agonists
  作者：Cecilia Mattsson、Peder Svensson、Henning Boettcher、Clas Sonesson

  DOI：10.1016/j.ejmech.2013.03.006

  日期：2013.5

  structure–activity relationship (SAR) of the 5-hydroxytryptamine type 6 (5-HT6) receptor agonist 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (EMD386088, 6), a series of 2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles were synthesized, and in vitro affinity to, and functional activity at 5-HT6 receptors was tested. We focused on substituents made at the indole N1-, 2- and 5-positions

  进一步研究5-羟基色胺6型（5-HT 6）受体激动剂5-氯-2-甲基-3-（1,2,3,6-四氢吡啶-4--4-基）-1 ħ -吲哚（EMD386088，6），一系列的2-甲基-3-（1,2,3,6-四氢吡啶-4-基）-1 ħ -indoles合成，并在体外亲和力，测试了5-HT 6受体的功能活性。我们专注于在吲哚N 1-，2-和5-位上制得的取代基，发现这些取代基不仅会影响5-HT 6上的亲和力受体和内在活性导致拮抗剂，部分激动剂和完全激动剂。为了使化合物表现出有效的5-HT 6受体激动剂特性，吲哚N 1应该未被取代，需要烷基如2-甲基，最后是吲哚5-位的卤素取代基（氟，氯或氯）。溴）是必不可少的要求。然而，在N 1位引入苯磺酰基使完全激动剂6变成5-HT 6受体拮抗剂（30）。2-甲基-3-（1,2,3,6-四氢吡啶-4--4-基）-1 H中的一些化合物还对-吲哚进行脱靶筛选，通常它们
• (Tétrahydro-1,2,3,6 pyridinyl-4)-3 1H-indoles: synthèse, propriétés sérotoninergique et anti-dopaminergiques
  作者：Jacques Guillaume、Claude Dumont、Jacques Laurent、Lucien Nédélec

  DOI：10.1016/0223-5234(87)90172-3

  日期：1987.1
• US3980658A
  申请人：——

  公开号：US3980658A

  公开（公告）日：1976-09-14
• 2-Alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles as novel 5-HT6 receptor agonists
  作者：Cecilia Mattsson、Clas Sonesson、Anna Sandahl、Hartmut E. Greiner、Michael Gassen、Jörg Plaschke、Joachim Leibrock、Henning Böttcher

  DOI：10.1016/j.bmcl.2005.06.067

  日期：2005.10

  A series of 2-alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles were synthesized and evaluated for their 5-HT6 activity. The most potent agonist in this series was 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole with an IC50 = 7.4 nM in H-3-LSD binding and an EC50 = 1.0 nM in a functional assay measuring production of cyclic AMP. (c) 2005 Elsevier Ltd. All rights reserved.