1-{5-[4-(1H-benzimidazol-4-yl)piperazin-1-yl]pentyl}-1,3-dihydro-2H-indol-2-one | 1146733-97-2

• 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-{5-[4-(1H-benzimidazol-4-yl)piperazin-1-yl]pentyl}-1,3-dihydro-2H-indol-2-one
• 英文别名: 1-[5-[4-(1H-benzimidazol-4-yl)piperazin-1-yl]pentyl]-3H-indol-2-one
• CAS: 1146733-97-2
• 化学式: C₂₄H₂₉N₅O
• 分子量: 403.527
• InChiKey: XNSRYAXPXINABJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-{5-[4-(1-trityl(1H)-benzimidazol-4-yl)piperazin-1-yl]pentyl}-1,3-dihydro-2H-indol-2-one 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 3.0h， 以58%的产率得到1-{5-[4-(1H-benzimidazol-4-yl)piperazin-1-yl]pentyl}-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.