2,3,4,9-tetrahydro-9-(phenylmethyl)-2-[2-(2-pyridinyl)ethyl]-1H-pyrido[3,4-b]indole | 116388-16-0

• 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: 2,3,4,9-tetrahydro-9-(phenylmethyl)-2-[2-(2-pyridinyl)ethyl]-1H-pyrido[3,4-b]indole
• 英文别名: 9-Benzyl-2-(2-pyridin-2-yl-ethyl)-2,3,4,9-tetrahydro-1H-beta-carboline；9-benzyl-2-(2-pyridin-2-ylethyl)-3,4-dihydro-1H-pyrido[3,4-b]indole
• CAS: 116388-16-0
• 化学式: C₂₅H₂₅N₃
• 分子量: 367.494
• InChiKey: QHDUKKOEVFYFNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2-溴乙基)吡啶氢溴酸盐 在 sodium hydride 、 potassium carbonate 、 caesium carbonate 、 potassium iodide 作用下， 反应 17.5h， 生成 2,3,4,9-tetrahydro-9-(phenylmethyl)-2-[2-(2-pyridinyl)ethyl]-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Psychotropic agents: synthesis and antipsychotic activity of substituted .beta.-carbolines

  摘要：

  A series of novel substituted beta-carbolines was synthesized and tested for potential antipsychotic activity. Several compounds displayed moderate antipsychotic activity in vitro and in vivo as determined by relevant receptor binding assays and behavioral tests. The effect of substituents on antipsychotic activity was examined. The beta-carbolines 10 and 19 containing 2-(2-pyridinyl)ethyl and 2-(2-quinolinyl)ethyl side chains were the most potent analogues, blocking discrete trial conditioned avoidance responding in rats with AB50's of 23 and 10 mg/kg, respectively. Both showed moderate activity at the D2 receptor sites, but they lacked oral activity. In contrast, the beta-carboline 13 containing the 4-(4-pyridinyl)butyl side chain exhibited oral activity in the discrete trial conditioned avoidance screen with an AB50 of 31 mg/kg. Most compounds did not antagonize apomorphine-induced stereotyped behavior, which is indicative of low potential for extrapyramidal side effect (EPS) liability.

  DOI：

  10.1021/jm00389a022

文献信息

• Carboline histamine H.sub.1 antagonists
  申请人：American Home Products Corporation

  公开号：US04754038A1

  公开（公告）日：1988-06-28

  Histaminic H.sub.1 -receptor antagonists of the formula: ##STR1## in which R.sup.1 is ##STR2## where R.sup.2 is hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, halo, nitro, cyano or trifluoromethyl; and R.sup.3 is hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, halo, nitro, cyano or trifluoromethyl; X is hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or halo; Z is ##STR3## where R.sup.4 is pyridinyl, quinolinyl or benzoyl, any of which may be substituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 3 carbon atoms, halo or trifluoromethyl; and m is one of the integers 2, 3 or 4; and n is one of the integers 1, 2, 3 or 4; or a pharmaceutically acceptable salt thereof.

  组成式为：##STR1##其中R.sup.1为##STR2##其中R.sup.2为氢、1至3个碳原子的烷基、1至3个碳原子的烷氧基、卤素、硝基、氰基或三氟甲基；而R.sup.3为氢、1至3个碳原子的烷基、1至3个碳原子的烷氧基、卤素、硝基、氰基或三氟甲基；X为氢、1至3个碳原子的烷基、1至3个碳原子的烷氧基或卤素；Z为##STR3##其中R.sup.4为吡啶基、喹啉基或苯甲酰基，其中任何一个可能被1至4个碳原子的烷基、1至3个碳原子的烷氧基、卤素或三氟甲基取代；m为2、3或4中的整数之一；n为1、2、3或4中的整数之一；或其药用盐。
• US4754038A
  申请人：——

  公开号：US4754038A

  公开（公告）日：1988-06-28
• Psychotropic agents: synthesis and antipsychotic activity of substituted .beta.-carbolines
  作者：Magid Abou-Gharbia、Usha R. Patel、John A. Moyer、Eric A. Muth

  DOI：10.1021/jm00389a022

  日期：1987.6

  A series of novel substituted beta-carbolines was synthesized and tested for potential antipsychotic activity. Several compounds displayed moderate antipsychotic activity in vitro and in vivo as determined by relevant receptor binding assays and behavioral tests. The effect of substituents on antipsychotic activity was examined. The beta-carbolines 10 and 19 containing 2-(2-pyridinyl)ethyl and 2-(2-quinolinyl)ethyl side chains were the most potent analogues, blocking discrete trial conditioned avoidance responding in rats with AB50's of 23 and 10 mg/kg, respectively. Both showed moderate activity at the D2 receptor sites, but they lacked oral activity. In contrast, the beta-carboline 13 containing the 4-(4-pyridinyl)butyl side chain exhibited oral activity in the discrete trial conditioned avoidance screen with an AB50 of 31 mg/kg. Most compounds did not antagonize apomorphine-induced stereotyped behavior, which is indicative of low potential for extrapyramidal side effect (EPS) liability.