ethyl 1-benzyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylate | 931399-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 1-benzyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylate
• 英文别名: ethyl 4-hvdroxy-6,7-bis(methyloxy)-2-oxo-1-(phenylmethyl)-1,2-dihydro-3-quinolinecarboxylate；Ethyl 1-benzyl-4-hydroxy-6,7-dimethoxy-2-oxoquinoline-3-carboxylate
• CAS: 931399-59-6
• 化学式: C₂₁H₂₁NO₆
• 分子量: 383.401
• InChiKey: NWXKHOHKPKTEGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1-benzyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylate 在 三溴化硼 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-benzyl-N-((1-benzylpiperidin-4-yl)methyl) 4,6,7-trihydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  Quinolone–benzylpiperidine derivatives as novel acetylcholinesterase inhibitor and antioxidant hybrids for Alzheimer Disease

  摘要：

  Design, synthesis and evaluation of new acetylcholinesterase inhibitors by combining quinolinecarboxamide to a benzylpiperidine moiety are described. Then, a series of hybrids have been developed by introducing radical scavengers. Molecular modeling was performed and structure activity relationships are discussed. Among the series, most potent compounds show effective AchE inhibitions, high selectivities over butyrylcholinesterase and high radical scavenging activities. On the basis of this work, the ability of quinolone derivatives to serve in the design of N-benzylpiperidine linked multipotent molecules for the treatment of Alzheimer Disease has been established. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.046
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 以240 mg的产率得到ethyl 1-benzyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Quinolone–benzylpiperidine derivatives as novel acetylcholinesterase inhibitor and antioxidant hybrids for Alzheimer Disease

  摘要：

  Design, synthesis and evaluation of new acetylcholinesterase inhibitors by combining quinolinecarboxamide to a benzylpiperidine moiety are described. Then, a series of hybrids have been developed by introducing radical scavengers. Molecular modeling was performed and structure activity relationships are discussed. Among the series, most potent compounds show effective AchE inhibitions, high selectivities over butyrylcholinesterase and high radical scavenging activities. On the basis of this work, the ability of quinolone derivatives to serve in the design of N-benzylpiperidine linked multipotent molecules for the treatment of Alzheimer Disease has been established. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.046

文献信息

• WO2007/38571
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] PROLYL HYDROXYLASE ANTAGONISTS<br/>[FR] ANTAGONISTES DE LA PROLYL-HYDROXYLASE
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2007038571A2

  公开（公告）日：2007-04-05

  [EN] This invention relates to certain 2-[(quinolin-3-yl)carbonyl]aminoacetic acid derivatives of formula (I), where the various groups are defined herein, and which are useful in treating anemia.
  [FR] Cette invention concerne certains dérivés d'acide 2-[(quinolin-3-yl)carbonyl]amino-acétique de formule (I) dans laquelle les divers groupes sont tels que définis dans le mémorandum descriptif. Ces dérivés sont utiles pour le traitement de l'anémie.
• Quinolone–benzylpiperidine derivatives as novel acetylcholinesterase inhibitor and antioxidant hybrids for Alzheimer Disease
  作者：Marc Pudlo、Vincent Luzet、Lhassane Ismaïli、Isabelle Tomassoli、Anne Iutzeler、Bernard Refouvelet

  DOI：10.1016/j.bmc.2014.02.046

  日期：2014.4

  Design, synthesis and evaluation of new acetylcholinesterase inhibitors by combining quinolinecarboxamide to a benzylpiperidine moiety are described. Then, a series of hybrids have been developed by introducing radical scavengers. Molecular modeling was performed and structure activity relationships are discussed. Among the series, most potent compounds show effective AchE inhibitions, high selectivities over butyrylcholinesterase and high radical scavenging activities. On the basis of this work, the ability of quinolone derivatives to serve in the design of N-benzylpiperidine linked multipotent molecules for the treatment of Alzheimer Disease has been established. (C) 2014 Elsevier Ltd. All rights reserved.