11-Methyl-4-[2-(4-quinolin-8-ylpiperazin-1-yl)ethyl]-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7),5-trien-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 11-Methyl-4-[2-(4-quinolin-8-ylpiperazin-1-yl)ethyl]-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7),5-trien-3-one
• 化学式: C₂₅H₂₈N₆OS
• 分子量: 460.603
• InChiKey: ATBLUNCHMMWNHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-(2-hydroxyethyl)-7-methyl-5,6,7,8-tetrahydropyrido[4', 3':4,5]thieno[2,3-d]pyrimidin-4(3H)-one 在 氯化亚砜 、 N,N-二异丙基乙胺 、 sodium bromide 作用下， 以 N-甲基吡咯烷酮 、 1,2-二氯乙烷 为溶剂， 生成 11-Methyl-4-[2-(4-quinolin-8-ylpiperazin-1-yl)ethyl]-8-thia-4,6,11-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7),5-trien-3-one
  参考文献：
  名称：

  Synthesis and SAR of highly potent dual 5-HT1A and 5-HT1B antagonists as potential antidepressant drugs

  摘要：

  Novel 5-HT1 autoreceptor ligands based on the N-4-aryl-piperazinyl-N'-ethyl-5,6,7,8-tetrahydropyrido[4', 3':4,5]thieno[2,3-d]pyrimidin-4(3H)-one core are described. Aiming at antidepressants with a novel mode of action our objective was to identify potent antagonists showing balanced affinities and high selectivity for the 5-HT1A and 5-HT1B receptors. Strategies for the development of dual 5-HT1A and 5-HT1B antagonists based on 1 and 2 as leads and the corresponding results are discussed. Isoquinoline analogue 33 displayed high affinity and an antagonistic mode of action for the 5-HT1A and the 5-HT1B receptors and was characterized further with respect to selectivity, electrically stimulated [H-3]5-HT release and in vivo efficacy. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2005.04.077

文献信息

• Synthesis and SAR of highly potent dual 5-HT1A and 5-HT1B antagonists as potential antidepressant drugs
  作者：Andreas Kling、Udo E.W. Lange、Helmut Mack、Margot H.M. Bakker、Karla U. Drescher、Wilfried Hornberger、Charles W. Hutchins、Achim Möller、Reinhold Müller、Martin Schmidt、Liliane Unger、Karsten Wicke、Kurt Schellhaas、Gerd Steiner

  DOI：10.1016/j.bmcl.2005.04.077

  日期：2005.12

  Novel 5-HT1 autoreceptor ligands based on the N-4-aryl-piperazinyl-N'-ethyl-5,6,7,8-tetrahydropyrido[4', 3':4,5]thieno[2,3-d]pyrimidin-4(3H)-one core are described. Aiming at antidepressants with a novel mode of action our objective was to identify potent antagonists showing balanced affinities and high selectivity for the 5-HT1A and 5-HT1B receptors. Strategies for the development of dual 5-HT1A and 5-HT1B antagonists based on 1 and 2 as leads and the corresponding results are discussed. Isoquinoline analogue 33 displayed high affinity and an antagonistic mode of action for the 5-HT1A and the 5-HT1B receptors and was characterized further with respect to selectivity, electrically stimulated [H-3]5-HT release and in vivo efficacy. (c) 2005 Published by Elsevier Ltd.