1,2-dihydro-8-methoxy-2-oxoquinoline-4-carboxylic acid | 37749-17-0

• 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: 1,2-dihydro-8-methoxy-2-oxoquinoline-4-carboxylic acid
• 英文别名: 8-methoxy-2-oxo-1,2-dihydro-quinoline-4-carboxylic acid；8-Methoxy-2-oxo-1,2-dihydrocinchoninic-acid；2-hydroxy-8-methoxyquinoline-4-carboxylic acid
• CAS: 37749-17-0
• 化学式: C₁₁H₉NO₄
• 分子量: 219.197
• InChiKey: ZIMKBZCDBGZJGS-UHFFFAOYSA-N

物化性质

• 沸点：
  440.8±45.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-8-methoxy-2-oxoquinoline-4-carboxylic acid 在 sodium hydroxide 、 硫脲 、 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 1.5h， 生成 8-methoxy-2-methylthioquinoline-4-carboxylic acid
  参考文献：
  名称：

  Fluorescence Properties of 2-Substituted 6-, 7- or 8-Methoxyquinoline-4-carboxylic Acid Derivatives.

  摘要：

  合成了 2-取代型 6-、7-或 8-甲氧基喹啉-4-羧酸衍生物。这些化合物的荧光量子产率（Φ）按照 6-甲氧基喹啉-4-羧酸的 2-硫酮-、2-甲硫基-、2-甲磺酰基-、2-甲磺酰基衍生物的顺序增加。在乙腈和乙醇中，6-甲氧基-2-甲磺酰基喹啉-4-羧酸乙酯（ΦCH3CN=0.74 或 ΦEtOH=0.69）的荧光量子产率远高于 7-和 8-甲氧基衍生物（ΦCH3CN=0.19 或 ΦEtOH=0.19，ΦCH3CN=0.16 或 ΦEtOH=0.05）。

  DOI：

  10.1248/cpb.40.1322
• 作为产物：
  描述：

  7-甲氧基靛红 、 丙二酸 在 溶剂黄146 作用下， 生成 1,2-dihydro-8-methoxy-2-oxoquinoline-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-oxo-1,2-dihydroquinoline-4-carboxamide derivatives for the treatment of esophageal squamous cell carcinoma

  摘要：

  No new and effective treatments have been approved for the treatment of esophageal squamous cell carcinoma (ESCC) in the past decade. Cisplatin and 5-fluoruracil are the most commonly used drugs for this disease. In order to develop a new class of drugs effective in our ESCC phenotypic screens, we began a systematic approach to generate novel compounds based on the 2-oxo-1,2-dihydroquinoline-4carboxamide fragment. Herein, we report on the synthesis and initial assessment of 55 new analogues in two ESCC cell lines. Some of the active analogues with 1050 values around 10 mu M were tested in three additional cell lines. Our structure-activity relationships revealed remarkable alterations in the anti proliferative activities upon modest chemical modifications and autophagy modulation is a suggested mechanism of action. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.05.042

文献信息

• Synthesis and biological evaluation of novel 2-oxo-1,2-dihydroquinoline-4-carboxamide derivatives for the treatment of esophageal squamous cell carcinoma
  作者：Mai I. Shahin、Joyeeta Roy、Maha Hanafi、Dongyao Wang、Urarika Luesakul、Yifeng Chai、Nongnuj Muangsin、Deena S. Lasheen、Dalal A. Abou El Ella、Khaled A. Abouzid、Nouri Neamati

  DOI：10.1016/j.ejmech.2018.05.042

  日期：2018.7

  No new and effective treatments have been approved for the treatment of esophageal squamous cell carcinoma (ESCC) in the past decade. Cisplatin and 5-fluoruracil are the most commonly used drugs for this disease. In order to develop a new class of drugs effective in our ESCC phenotypic screens, we began a systematic approach to generate novel compounds based on the 2-oxo-1,2-dihydroquinoline-4carboxamide fragment. Herein, we report on the synthesis and initial assessment of 55 new analogues in two ESCC cell lines. Some of the active analogues with 1050 values around 10 mu M were tested in three additional cell lines. Our structure-activity relationships revealed remarkable alterations in the anti proliferative activities upon modest chemical modifications and autophagy modulation is a suggested mechanism of action. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Fluorescence Properties of 2-Substituted 6-, 7- or 8-Methoxyquinoline-4-carboxylic Acid Derivatives.
  作者：Tomohiko YOSHIDA、Youichi MORIYAMA、Saburo NAKANO

  DOI：10.1248/cpb.40.1322

  日期：——

  2-Substituted 6-, 7- or 8-methoxyquinoline-4-carboxylic acid derivatives were synthesized. The fluorescence quantum yield (Φ) of these compounds increased in the order, 2-thioxo-, 2-methylthio-, 2-methylsulfinyl-, 2-methylsulfonyl derivatives of 6-methoxyquinoline-4-carboxylic acid. Ethyl 6-methoxy-2-methylsulfonylquinoline-4-carboxylate (ΦCH3CN=0.74 or ΦEtOH=0.69) showed a much higher fluorescence quantum yield than those (ΦCH3CN=0.19 or ΦEtOH=0.19 and ΦCH3CN=0.16 or ΦEtOH=0.05) of the 7- and 8-methoxy derivatives in both acetonitrile and ethanol.

  合成了 2-取代型 6-、7-或 8-甲氧基喹啉-4-羧酸衍生物。这些化合物的荧光量子产率（Φ）按照 6-甲氧基喹啉-4-羧酸的 2-硫酮-、2-甲硫基-、2-甲磺酰基-、2-甲磺酰基衍生物的顺序增加。在乙腈和乙醇中，6-甲氧基-2-甲磺酰基喹啉-4-羧酸乙酯（ΦCH3CN=0.74 或 ΦEtOH=0.69）的荧光量子产率远高于 7-和 8-甲氧基衍生物（ΦCH3CN=0.19 或 ΦEtOH=0.19，ΦCH3CN=0.16 或 ΦEtOH=0.05）。