5-[(Z)-2-(4-fluorophenyl)vinyl]-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole | 1208230-72-1

• 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-[(Z)-2-(4-fluorophenyl)vinyl]-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
• 英文别名: 5-[(Z)-2-(4-fluorophenyl)ethenyl]-2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole
• CAS: 1208230-72-1
• 化学式: C₂₁H₂₁FN₂
• 分子量: 320.41
• InChiKey: SLKYZAGABKKIDN-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-[(Z)-2-(4-fluorophenyl)vinyl]-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 在 platinum(IV) oxide 、 氢气 作用下， 反应 12.0h， 生成 5-[2-(4-fluorophenyl)ethyl]-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Synthesis and biological activity of 5-styryl and 5-phenethyl-substituted 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.11.037
• 作为产物：
  描述：

  4-氟苯乙炔 、 2,8-二甲基-2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚 在 四正丁基硫酸铵 、 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 trans-2,8-dimethyl-5-[2-(4-fluorophenyl)ethenyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 、 5-[(Z)-2-(4-fluorophenyl)vinyl]-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Synthesis and biological activity of 5-styryl and 5-phenethyl-substituted 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.11.037

文献信息

• 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.