1-{(2E)-4-[4-(1-naphthyl)piperazin-1-yl]but-2-enyl}-1,3-dihydro-2H-indol-2-one | 1146733-99-4

• 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: 1-{(2E)-4-[4-(1-naphthyl)piperazin-1-yl]but-2-enyl}-1,3-dihydro-2H-indol-2-one
• 英文别名: 1-[(E)-4-(4-naphthalen-1-ylpiperazin-1-yl)but-2-enyl]-3H-indol-2-one
• CAS: 1146733-99-4
• 化学式: C₂₆H₂₇N₃O
• 分子量: 397.52
• InChiKey: GIFYHUSNALLKOZ-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-{(2E)-4-[4-(1-naphthyl)piperazin-1-yl]but-2-enyl}-1,3-dihydro-2H-indol-2-one 在 盐酸 作用下， 以 水 为溶剂， 生成 1-{(2E)-4-[4-(1-naphthyl)piperazin-1-yl]but-2-enyl}-1,3-dihydro-2H-indol-2-one dihydrochloride
  参考文献：
  名称：

  Synthesis of New Serotonin 5-HT₇ Receptor Ligands. Determinants of 5-HT₇/5-HT_1A Receptor Selectivity

  摘要：

  We report the synthesis of a new set of compounds of general structure I (1-20) with structural modifications in the pharmacophoric elements of the previously reported lead UCM-5600. The new derivatives have been evaluated for binding affinity at 5-HT7 and 5-HT1A receptors. The influence of the different structural features in terms of 5-HT7/5-HT1A receptor affinity and selectivity was analyzed by computational simulations of the complexes between compounds I and beta(2)-based 3-D models of these receptors. Compound 18 (HYD1 = 1,3-dihydro-2H-indol-2-one; spacer = -(CH2)(4)-; HYD2 + HYD3 = 3,4-dihydroisoquinolin-2(1H)-yl) exhibits high 5-HT7R affinity (K-i = 7 nM) and selectivity over the 5-HT1AR (31-fold), and has been characterized as a partial agonist of the human 5-HT7R.

  DOI：

  10.1021/jm8014553
• 作为产物：
  描述：

  1-(1-萘基)对二氮已环 、 1-[(2E)-4-chlorobut-2-enyl]-1,3-dihydro-2H-indol-2-one 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以44%的产率得到1-{(2E)-4-[4-(1-naphthyl)piperazin-1-yl]but-2-enyl}-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  Synthesis of New Serotonin 5-HT₇ Receptor Ligands. Determinants of 5-HT₇/5-HT_1A Receptor Selectivity

  摘要：

  We report the synthesis of a new set of compounds of general structure I (1-20) with structural modifications in the pharmacophoric elements of the previously reported lead UCM-5600. The new derivatives have been evaluated for binding affinity at 5-HT7 and 5-HT1A receptors. The influence of the different structural features in terms of 5-HT7/5-HT1A receptor affinity and selectivity was analyzed by computational simulations of the complexes between compounds I and beta(2)-based 3-D models of these receptors. Compound 18 (HYD1 = 1,3-dihydro-2H-indol-2-one; spacer = -(CH2)(4)-; HYD2 + HYD3 = 3,4-dihydroisoquinolin-2(1H)-yl) exhibits high 5-HT7R affinity (K-i = 7 nM) and selectivity over the 5-HT1AR (31-fold), and has been characterized as a partial agonist of the human 5-HT7R.

  DOI：

  10.1021/jm8014553

文献信息

• Synthesis of New Serotonin 5-HT₇ Receptor Ligands. Determinants of 5-HT₇/5-HT_1A Receptor Selectivity
  作者：Rocío A. Medina、Jessica Sallander、Bellinda Benhamú、Esther Porras、Mercedes Campillo、Leonardo Pardo、María L. López-Rodríguez

  DOI：10.1021/jm8014553

  日期：2009.4.23

  We report the synthesis of a new set of compounds of general structure I (1-20) with structural modifications in the pharmacophoric elements of the previously reported lead UCM-5600. The new derivatives have been evaluated for binding affinity at 5-HT7 and 5-HT1A receptors. The influence of the different structural features in terms of 5-HT7/5-HT1A receptor affinity and selectivity was analyzed by computational simulations of the complexes between compounds I and beta(2)-based 3-D models of these receptors. Compound 18 (HYD1 = 1,3-dihydro-2H-indol-2-one; spacer = -(CH2)(4)-; HYD2 + HYD3 = 3,4-dihydroisoquinolin-2(1H)-yl) exhibits high 5-HT7R affinity (K-i = 7 nM) and selectivity over the 5-HT1AR (31-fold), and has been characterized as a partial agonist of the human 5-HT7R.