2-{(1H-pyrrolo[2,3-b]pyridin-3-yl)methyl}-5-(4-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptane | 1136651-09-6

• 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: 2-{(1H-pyrrolo[2,3-b]pyridin-3-yl)methyl}-5-(4-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptane
• 英文别名: 3-[[5-(4-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]methyl]-1H-pyrrolo[2,3-b]pyridine
• CAS: 1136651-09-6
• 化学式: C₁₉H₁₉ClN₄
• 分子量: 338.84
• InChiKey: YOODWDNGWLMMGG-UHFFFAOYSA-N

物化性质

• 熔点：
  176-178 °C
• 密度：
  1.369±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-氮杂吲哚 、 2-(4-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptane 、 聚合甲醛 在 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-{(1H-pyrrolo[2,3-b]pyridin-3-yl)methyl}-5-(4-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Synthesis and evaluation of ligands for D2-like receptors: The role of common pharmacophoric groups

  摘要：

  Arylcycloalkylamines, such as phenyl piperidines and piperazines and their arylalkyl substituents, constitute pharmacophoric groups exemplified in several antipsychotic agents. A review of previous reports indicates that arylalkyl substituents can improve the potency and selectivity of the binding affinity at D-2-like receptors. In this paper, we explored the contributions of two key pharmacophoric groups, that is, 40-fluorobutyrophenones and 3-methyl-7-azaindoles, to the potency and selectivity of synthesized agents at D-2-like receptors. Preliminary observation of binding affinities indicates that there is little predictability of specific effects of the arylalkyl moieties but the composite structure is responsible for selectivity and potency at these receptors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.12.054

文献信息

• Synthesis and evaluation of ligands for D2-like receptors: The role of common pharmacophoric groups
  作者：Donald M.N. Sikazwe、Nancy T. Nkansah、Ramazan Altundas、Xue Y. Zhu、Bryan L. Roth、Vincent Setola、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2008.12.054

  日期：2009.2

  Arylcycloalkylamines, such as phenyl piperidines and piperazines and their arylalkyl substituents, constitute pharmacophoric groups exemplified in several antipsychotic agents. A review of previous reports indicates that arylalkyl substituents can improve the potency and selectivity of the binding affinity at D-2-like receptors. In this paper, we explored the contributions of two key pharmacophoric groups, that is, 40-fluorobutyrophenones and 3-methyl-7-azaindoles, to the potency and selectivity of synthesized agents at D-2-like receptors. Preliminary observation of binding affinities indicates that there is little predictability of specific effects of the arylalkyl moieties but the composite structure is responsible for selectivity and potency at these receptors. Published by Elsevier Ltd.