4-Oxo-1-[(4-phenyl-1-piperidinyl)methyl]-4H-quinolizine-3-carboxylic acid | 1181964-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-Oxo-1-[(4-phenyl-1-piperidinyl)methyl]-4H-quinolizine-3-carboxylic acid
• 英文别名: 4-oxo-1-[(4-phenylpiperidin-1-yl)methyl]quinolizine-3-carboxylic acid
• CAS: 1181964-81-7
• 化学式: C₂₂H₂₂N₂O₃
• 分子量: 362.428
• InChiKey: LBBKUZMYCIQSRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-甲酰基-4-氧代-4H-羟基喹啉-3-羧酸乙酯 在 乙醇 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 4-Oxo-1-[(4-phenyl-1-piperidinyl)methyl]-4H-quinolizine-3-carboxylic acid
  参考文献：
  名称：

  Quinolizidinone carboxylic acid selective M1 allosteric modulators: SAR in the piperidine series

  摘要：

  SAR study of the piperidine moiety in a series of quinolizidinone carboxylic acid M1 positive allosteric modulators was examined. While the SAR was generally flat, compounds were identified with high CNS exposure to warrant additional in vivo evaluation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.094

文献信息

• Quinolizidinone Carboxylic Acids as CNS Penetrant, Selective M₁ Allosteric Muscarinic Receptor Modulators
  作者：Scott D. Kuduk、Ronald K. Chang、Christina N. Di Marco、William J. Ray、Lei Ma、Marion Wittmann、Matthew A. Seager、Kenneth A. Koeplinger、Charles D. Thompson、George D. Hartman、Mark T. Bilodeau

  DOI：10.1021/ml100095k

  日期：2010.9.9

  Positive allosteric modulation of the M, muscarinic receptor represents an approach to treat the cognitive decline in patients with Alzheimer's disease. Replacement of a quinolone ring system in a quinolone carboxylic acid series of M, modulators with a quinolizidinone bearing a basic amine linkage led to a series of compounds with higher free fraction, enhanced CNS exposure, and improved efficacy in rodent in vivo models of cognition.
• Quinolizidinone carboxylic acid selective M1 allosteric modulators: SAR in the piperidine series
  作者：Scott D. Kuduk、Ronald K. Chang、Christina N. Di Marco、William J. Ray、Lei Ma、Marion Wittmann、Matthew A. Seager、Kenneth A. Koeplinger、Charles D. Thompson、George D. Hartman、Mark T. Bilodeau

  DOI：10.1016/j.bmcl.2011.01.094

  日期：2011.3

  SAR study of the piperidine moiety in a series of quinolizidinone carboxylic acid M1 positive allosteric modulators was examined. While the SAR was generally flat, compounds were identified with high CNS exposure to warrant additional in vivo evaluation. (C) 2011 Elsevier Ltd. All rights reserved.