2,8-dimethyl-5-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole monohydrochloride | 1061354-48-0

• 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: 2,8-dimethyl-5-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole monohydrochloride
• 英文别名: 2,8-dimethyl-5-phenethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride；2,8-dimethyl-5-(2-phenethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride；2,8-dimethyl-5-phenethyl-1,2,3,4-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride；2,8-Dimethyl-5-phenethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride；2,8-dimethyl-5-(2-phenylethyl)-3,4-dihydro-1H-pyrido[4,3-b]indole;hydrochloride
• CAS: 1061354-48-0
• 化学式: C₂₁H₂₄N₂*ClH
• 分子量: 340.896
• InChiKey: RKLJJDFIWWRTEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  8.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  非维匹仑 生成 2,8-dimethyl-5-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole monohydrochloride
  参考文献：
  名称：

  SUSTITUTED 2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLES, METHODS FOR USE THEREOF

  摘要：

  本发明涉及一种拮抗5-HT6 5-羟色胺受体和同时调节细胞内Ca+2离子稳态的方法，包括向细胞中投与式1的化合物或其药学上可接受的盐，其中：R1是C1-C5烷基；R2独立地是氢、卤素、C1-C3烷基、CF3、OCF3或OCH3；i为1、2、3或4；Ar是未取代的苯基或取代的苯基，其被卤素、C1-C6烷基、C1-C6烷氧基、取代的氨基团或三氟甲基取代；或Ar是带有一个或两个氮原子的取代或未取代的6元芳香杂环；W是乙烯基—CH2—CH2—、乙烯基—CH═CH—或乙炔基—C≡C—。本发明还涉及从式1的化合物组中选择的新化合物、其制备方法、制备药物组合物的方法以及治疗认知障碍或神经退行性疾病或肥胖症的方法，包括向需要治疗的受体中投与式1的化合物或其药学上可接受的盐的有效剂量。

  公开号：

  US20130217703A1

文献信息

• SUSTITUTED 2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLES, METHODS FOR USE THEREOF
  申请人：Alla Chem, LLC

  公开号：US20130217703A1

  公开（公告）日：2013-08-22

  The present invention relates to a method of antagonizing a 5-HT 6 serotonin receptor and simultaneously regulating Ca +2 ion homeostasis in a cell, comprising administering to the cell a compound of formula 1, or a pharmaceutically acceptable salt thereof, wherein: R 1 is a C 1 -C 5 alkyl; R 2 i is independently hydrogen, halogen, a C 1 -C 3 alkyl, CF 3 , OCF 3 or OCH 3 ; i is 1, 2, 3 or 4; Ar is an unsubstituted phenyl or a substituted phenyl substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, substituted amino group or trifluoromethyl; or Ar is a substituted or unsubstituted 6-membered aromatic heterocycle with one or two nitrogen atoms in the heterocycle; and W is an ethylene group —CH 2 —CH 2 —, ethenyl group —CH═CH—, or ethynyl group —C≡C—. The invention also relates to new compounds selected from the group of compounds of the general formula 1, method for their preparation, pharmaceutical compositions and method for treating a cognitive disorder or neurodegenerative disease, or obesity in a subject in need thereof comprising administering an effective dose to the subject of a compound of formula 1 according to claim 1 , or a pharmaceutically acceptable salt thereof.

  本发明涉及一种拮抗5-HT6 5-羟色胺受体和同时调节细胞内Ca+2离子稳态的方法，包括向细胞中投与式1的化合物或其药学上可接受的盐，其中：R1是C1-C5烷基；R2独立地是氢、卤素、C1-C3烷基、CF3、OCF3或OCH3；i为1、2、3或4；Ar是未取代的苯基或取代的苯基，其被卤素、C1-C6烷基、C1-C6烷氧基、取代的氨基团或三氟甲基取代；或Ar是带有一个或两个氮原子的取代或未取代的6元芳香杂环；W是乙烯基—CH2—CH2—、乙烯基—CH═CH—或乙炔基—C≡C—。本发明还涉及从式1的化合物组中选择的新化合物、其制备方法、制备药物组合物的方法以及治疗认知障碍或神经退行性疾病或肥胖症的方法，包括向需要治疗的受体中投与式1的化合物或其药学上可接受的盐的有效剂量。
• Synthesis and biological activity of 5-styryl and 5-phenethyl-substituted 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles
  作者：Alexandre V. Ivachtchenko、Eugen B. Frolov、Oleg D. Mitkin、Sergei E. Tkachenko、Ilya M. Okun、Alex V. Khvat

  DOI：10.1016/j.bmcl.2009.11.037

  日期：2010.1

  Syntheses, biological evaluation, and structure-activity relationships for a series of novel 5-styryl and 5-phenethyl analogs of dimebolin are disclosed. The novel derivatives and dimebolin share a broad spectrum of activities against therapeutically relevant targets. Among all synthesized derivatives, 2,8-dimethyl-5-[(Z)-2-phenylvinyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole and its 5-phenethyl analog are the most potent blockers of 5-HT(7), 5-HT(6), 5-HT(2C), Adrenergic alpha(2) and H(1) receptors. The general affinity rank order towards the studied receptors was Z-3(2) >= 4(2) P4(3) >> dimebolin, all of them having highest affinities to 5-HT7 receptors. (C) 2009 Elsevier Ltd. All rights reserved.
• EP2236511
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• EP4137208
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• Bioorg. Med. Chem. Lett. 2010, 20, 78-82
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