1-acetyl-5-amino-7,8-dimethoxy-2,3-dihydro-1H-quinolin-4-one | 436810-40-1

• 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: 1-acetyl-5-amino-7,8-dimethoxy-2,3-dihydro-1H-quinolin-4-one
• 英文别名: 1-Acetyl-5-amino-7,8-dimethoxy-2,3-dihydroquinolin-4-one
• CAS: 436810-40-1
• 化学式: C₁₃H₁₆N₂O₄
• 分子量: 264.281
• InChiKey: KNJFMQRSXUPSDP-UHFFFAOYSA-N

物化性质

• 熔点：
  173 °C
• 沸点：
  580.8±50.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-acetyl-5-amino-7,8-dimethoxy-2,3-dihydro-1H-quinolin-4-one 在 palladium on activated charcoal 盐酸 、 甲酸铵 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 生成 3-[(15,16-Dimethoxy-12,18-diazapentacyclo[11.7.1.02,11.05,10.017,21]henicosa-1,5(10),6,8,11,13,15,17(21)-octaen-7-yl)oxy]propan-1-amine
  参考文献：
  名称：

  Highly cytotoxic benzo[c]pyrido[2,3,4-kl]acridines

  摘要：

  Several benzo[c]pyrido[2,3,4-kl]acridines bearing different substituents on the A and E rings were synthesized and evaluated for their capacity to bind to DNA and to inhibit DNA topoisomerases. Potent cytotoxic compounds were discovered but no strict correlation with their DNA binding affinity and effects on topoisomerases were observed. DNA is one but not the unique target of these compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01066-1
• 作为产物：
  描述：

  N-(ethoxycarbonyl)-2,3-dimethoxyaniline 在 氢氧化钾 、 硫酸 、 硝酸 、 铁粉 作用下， 以 吡啶 、 乙醇 、 水 、 溶剂黄146 、 甲苯 、 乙腈 为溶剂， 反应 24.58h， 生成 1-acetyl-5-amino-7,8-dimethoxy-2,3-dihydro-1H-quinolin-4-one
  参考文献：
  名称：

  有效合成新的苯并[c]吡啶基[2,3,4-kl] ac啶骨架。

  摘要：

  通过Friedländer方法合成了一系列具有治疗意义的分子，这些分子具有1H-苯并[c]吡啶基[2,3,4-kl] ac啶的新骨架，芳族同环上具有酰基或氨基酰基以及甲氧基或氨基烷氧基取代基型反应。使用共沸条件下的酸性催化剂（PPTS），将必要的5-氨基二氢喹啉4-ones 1（其制备方法已描述）与适当的α-四氢萘酮2反应。优化的反应时间和产率取决于温度，温度不得低于90摄氏度。

  DOI：

  10.1021/jo011057m

文献信息

• DNA Binding To Guide the Development of Tetrahydroindeno[1,2-<i>b</i>]pyrido[4,3,2-<i>d</i><i>e</i>]quinoline Derivatives as Cytotoxic Agents
  作者：Sarah Catoen-Chackal、Michael Facompré、Raymond Houssin、Nicole Pommery、Jean-François Goossens、Pierre Colson、Christian Bailly、Jean-Pierre Hénichart

  DOI：10.1021/jm0400193

  日期：2004.7.1

  The tetrahydroindeno[1,2-b]pyrido[4,3,2-de]quinoline chromophore was initially designed as a DNA intercalating unit because of its planar structure. Unexpectedly, one molecule (15d) bearing two N-methylpiperazine chains on both sides of this condensed pentacyclic skeleton fits into the minor groove of DNA and preferentially recognizes AT-rich sequences. The monosubstituted compound 16d was identified as a potent cytotoxic DNA intercalator, whereas the disubstituted analogue 15d represents a new structural motif for the development of DNA sequence-reading small molecules.
• An Efficient Synthesis of the New Benzo[<i>c</i>]pyrido[2,3,4-<i>kl</i>]acridine Skeleton
  作者：Sarah Chackal、Raymond Houssin、Jean-Pierre Hénichart

  DOI：10.1021/jo011057m

  日期：2002.5.1

  A series of molecules of therapeutic interest, possessing the new skeleton of 1H-benzo[c]pyrido[2,3,4-kl]acridine with acyl or aminoacyl and methoxy or aminoalkoxy substituents on the aromatic homocycles were synthesized by means of a Friedländer-type reaction. The requisite 5-aminodihydroquinoline-4-ones 1, whose preparation is described, were reacted with the appropriate alpha-tetralones 2 using

  通过Friedländer方法合成了一系列具有治疗意义的分子，这些分子具有1H-苯并[c]吡啶基[2,3,4-kl] ac啶的新骨架，芳族同环上具有酰基或氨基酰基以及甲氧基或氨基烷氧基取代基型反应。使用共沸条件下的酸性催化剂（PPTS），将必要的5-氨基二氢喹啉4-ones 1（其制备方法已描述）与适当的α-四氢萘酮2反应。优化的反应时间和产率取决于温度，温度不得低于90摄氏度。
• Highly cytotoxic benzo[c]pyrido[2,3,4-kl]acridines
  作者：Sarah Chackal、Michael Facompré、Raymond Houssin、Jean-François Goossens、Nicole Pommery、Jean-Pierre Hénichart、Christian Bailly

  DOI：10.1016/s0960-894x(02)01066-1

  日期：2003.3

  Several benzo[c]pyrido[2,3,4-kl]acridines bearing different substituents on the A and E rings were synthesized and evaluated for their capacity to bind to DNA and to inhibit DNA topoisomerases. Potent cytotoxic compounds were discovered but no strict correlation with their DNA binding affinity and effects on topoisomerases were observed. DNA is one but not the unique target of these compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.