methyl 2-(1,2-dihydroquinolin-2-ylidene)-3-oxobutanoate | 69582-84-9

• 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: methyl 2-(1,2-dihydroquinolin-2-ylidene)-3-oxobutanoate
• 英文别名: methyl 3-oxo-2-(1H-quinolin-2-ylidene)butanoate
• CAS: 69582-84-9
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: ANQQCWWUMUNVAR-UHFFFAOYSA-N

物化性质

• 熔点：
  119.5-120.5 °C(Solv: methanol (67-56-1))
• 沸点：
  398.1±42.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(1,2-dihydroquinolin-2-ylidene)-3-oxobutanoate 在 盐酸 作用下， 以 水 为溶剂， 以58%的产率得到2-(喹啉-2-基)乙酸甲酯
  参考文献：
  名称：

  [EN] CARBAMIC ACID COMPOUNDS COMPRISING A BICYCLIC HETEROARYL GROUP AS HDAC INHIBITORS
  [FR] COMPOSES D'ACIDE CARBAMIQUE COMPRENANT UN GROUPE HETEROARYLE BICYCLIQUE UTILISES EN TANT QU'INHIBITEURS DE HDAC

  摘要：

  公开号：

  WO2004076386A3
• 作为产物：
  描述：

  喹啉-N-氧化物 、 乙酰乙酸甲酯 在 乙酸酐 作用下， 反应 9.0h， 以36%的产率得到methyl 2-(1,2-dihydroquinolin-2-ylidene)-3-oxobutanoate
  参考文献：
  名称：

  Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides

  摘要：

  N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero) aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.002

文献信息

• [EN] CARBAMIC ACID COMPOUNDS COMPRISING A BICYCLIC HETEROARYL GROUP AS HDAC INHIBITORS<br/>[FR] COMPOSES D'ACIDE CARBAMIQUE COMPRENANT UN GROUPE HETEROARYLE BICYCLIQUE UTILISES EN TANT QU'INHIBITEURS DE HDAC
  申请人：TOPOTARGET UK LTD

  公开号：WO2004076386A3

  公开（公告）日：2004-10-28
• Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides
  作者：Pranjal K. Baruah、Jason Dinsmore、Amber M. King、Christophe Salomé、Marc De Ryck、Rafal Kaminski、Laurent Provins、Harold Kohn

  DOI：10.1016/j.bmc.2012.04.002

  日期：2012.6

  N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero) aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model. (C) 2012 Elsevier Ltd. All rights reserved.