N-methyl-N-{1-[3-(3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-propyl]-piperidin-4-yl}-2-phenyl-acetamide | 1242436-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: N-methyl-N-{1-[3-(3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-propyl]-piperidin-4-yl}-2-phenyl-acetamide
• 英文别名: N-methyl-N-[1-[3-(3-oxo-1,4-benzoxazin-4-yl)propyl]piperidin-4-yl]-2-phenylacetamide
• CAS: 1242436-67-4
• 化学式: C₂₅H₃₁N₃O₃
• 分子量: 421.539
• InChiKey: JRLRPPKTYBXZTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  53.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(3-bromopropyl)-2H-benzo[b][1,4]oxazin-3(4H)-one 、 N-Methyl-N-4-piperidinyl-benzeneacetamide 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-methyl-N-{1-[3-(3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-propyl]-piperidin-4-yl}-2-phenyl-acetamide
  参考文献：
  名称：

  Discovery of N-{1-[3-(3-Oxo-2,3-dihydrobenzo[1,4]oxazin-4-yl)propyl]piperidin-4-yl}-2-phenylacetamide (Lu AE51090): An Allosteric Muscarinic M₁ Receptor Agonist with Unprecedented Selectivity and Procognitive Potential

  摘要：

  The discovery and structure activity relationship (SAR) of a series of allosteric muscarinic M, receptor agonists are described. Compound 17 (Lu AE51090) was identified as a representative compound from the series, based on its high selectivity as an agonist at the muscarinic M-1 receptor across a panel of muscarinic receptor subtypes. Furthermore, 17 displayed a high degree of selectivity when tested in a broad panel of G-protein-coupled receptors, ion channels, transporters, and enzymes, and 17 showed an acceptable pharmacokinetic profile and sufficient brain exposure in rodents in order to characterize the compound in vivo. Hence, in a rodent model of learning and memory, 17 reversed delay-induced natural forgetting, suggesting a procognitive potential of 17.

  DOI：

  10.1021/jm100697g

文献信息

• Discovery of <i>N</i>-{1-[3-(3-Oxo-2,3-dihydrobenzo[1,4]oxazin-4-yl)propyl]piperidin-4-yl}-2-phenylacetamide (Lu AE51090): An Allosteric Muscarinic M₁ Receptor Agonist with Unprecedented Selectivity and Procognitive Potential
  作者：Anette G. Sams、Morten Hentzer、Gitte K. Mikkelsen、Krestian Larsen、Christoffer Bundgaard、Niels Plath、Claus T. Christoffersen、Benny Bang-Andersen

  DOI：10.1021/jm100697g

  日期：2010.9.9

  The discovery and structure activity relationship (SAR) of a series of allosteric muscarinic M, receptor agonists are described. Compound 17 (Lu AE51090) was identified as a representative compound from the series, based on its high selectivity as an agonist at the muscarinic M-1 receptor across a panel of muscarinic receptor subtypes. Furthermore, 17 displayed a high degree of selectivity when tested in a broad panel of G-protein-coupled receptors, ion channels, transporters, and enzymes, and 17 showed an acceptable pharmacokinetic profile and sufficient brain exposure in rodents in order to characterize the compound in vivo. Hence, in a rodent model of learning and memory, 17 reversed delay-induced natural forgetting, suggesting a procognitive potential of 17.