4-hydroxy-3-[3-(4-methoxyphenyl)-1-oxo-2-propen-1-yl]-2(1Η)-quinolinone | 163232-52-8

• 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: 4-hydroxy-3-[3-(4-methoxyphenyl)-1-oxo-2-propen-1-yl]-2(1Η)-quinolinone
• 英文别名: 4-hydroxy-3-[3-(4-methoxyphenyl)prop-2-enoyl]-1H-quinolin-2-one
• CAS: 163232-52-8
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: RENGDZIGCFNTHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  4-hydroxy-3-[3-(4-methoxyphenyl)-1-oxo-2-propen-1-yl]-2(1Η)-quinolinone 、 邻苯二胺 在 溶剂黄146 作用下， 以77%的产率得到4-hydroxy-3-(2-(4-methoxyphenyl)-2,3-dihydro-1H-benzo[b][1,4]diazepin-4-yl)quinolin-2(1H)-one
  参考文献：
  名称：

  合成生物活性吡唑，异恶唑和苯并二氮杂‐取代的喹啉2（1H）-1衍生物的简便方法

  摘要：

  从易于获得的起始前体开始，以高收率合成了一系列功能化的吡唑，异恶唑和苯并二氮杂取代的喹诺酮衍生物。这些方法可以通过常规方法和微波辅助方法合成迄今未知的具有不同取代模式的化合物。通过MTT方案评估了大量类似物对人宫颈癌和结肠癌细胞系的体外细胞毒性。几乎所有选择的化合物都显示出显着的细胞毒性活性。其中，化合物4g和4i成为最有前途的支架。这些支架将用于进一步的分子水平研究。

  DOI：

  10.1002/jhet.2192
• 作为产物：
  描述：

  邻乙酰胺苯甲酸內酯 在 哌啶 、 potassium tert-butylate 、 sodium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 叔丁醇 为溶剂， 生成 4-hydroxy-3-[3-(4-methoxyphenyl)-1-oxo-2-propen-1-yl]-2(1Η)-quinolinone
  参考文献：
  名称：

  Synthesis and anti-parasitic activity of a novel quinolinone–chalcone series

  摘要：

  A series of novel quinolinone-chalcone hybrids and analogues were designed, synthesized and their biological activity against the mammalian stages of Trypanosoma brucei and Leishmania infantum evaluated. Promising molecular scaffolds with significant microbicidal activity and low cytotoxicity were identified. Quinolinone-chalcone 10 exhibited anti-parasitic properties against both organisms, being the most potent anti-L. infantum agent of the entire series (IC50 value of 1.3 +/- 0.1 mu M). Compounds 4 and 11 showed potency toward the intracellular, amastigote stage of L. infantum (IC50 values of 2.1 +/- 0.6 and 3.1 +/- 1.05 mu M, respectively). Promising trypanocidal compounds include 5 and 10 (IC50 values of 2.6 +/- 0.1 and 3.3 +/- 0.1 mu M, respectively) as well as 6 and 9 (both having IC50 values of <5 mu M). Chemical modifications on the quinolinone-chalcone scaffold were performed on selected compounds in order to investigate the influence of these structural features on antiparasitic activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.047

文献信息

• Bhupathi, Raja S.; Rama Devi; Dubey, Asian Journal of Chemistry, 2011, vol. 23, # 9, p. 4215 - 4218
  作者：Bhupathi, Raja S.、Rama Devi、Dubey

  DOI：——

  日期：——
• Bhupathi, Raja S.; Devi, B. Rama; Dubey, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 6, p. 855 - 859
  作者：Bhupathi, Raja S.、Devi, B. Rama、Dubey

  DOI：——

  日期：——
• Synthesis and anti-parasitic activity of a novel quinolinone–chalcone series
  作者：Marina Roussaki、Belinda Hall、Sofia Costa Lima、Anabela Cordeiro da Silva、Shane Wilkinson、Anastasia Detsi

  DOI：10.1016/j.bmcl.2013.09.047

  日期：2013.12

  A series of novel quinolinone-chalcone hybrids and analogues were designed, synthesized and their biological activity against the mammalian stages of Trypanosoma brucei and Leishmania infantum evaluated. Promising molecular scaffolds with significant microbicidal activity and low cytotoxicity were identified. Quinolinone-chalcone 10 exhibited anti-parasitic properties against both organisms, being the most potent anti-L. infantum agent of the entire series (IC50 value of 1.3 +/- 0.1 mu M). Compounds 4 and 11 showed potency toward the intracellular, amastigote stage of L. infantum (IC50 values of 2.1 +/- 0.6 and 3.1 +/- 1.05 mu M, respectively). Promising trypanocidal compounds include 5 and 10 (IC50 values of 2.6 +/- 0.1 and 3.3 +/- 0.1 mu M, respectively) as well as 6 and 9 (both having IC50 values of <5 mu M). Chemical modifications on the quinolinone-chalcone scaffold were performed on selected compounds in order to investigate the influence of these structural features on antiparasitic activity. (C) 2013 Elsevier Ltd. All rights reserved.
• An Expedient Approach for the Synthesis of Bioactive Pyrazole, Isoxazole and Benzodiazepine-Substituted Quinolin-2(1<i>H</i>)-one Derivatives
  作者：Mathan Sankaran、Chokkalingam Uvarani、Kumarasamy Chandraprakash、Mani Umamaheswari、Palathurai Subramaniam Mohan

  DOI：10.1002/jhet.2192

  日期：2015.7

  These approaches lead to the synthesis of hitherto unknown compounds with a varied substitution pattern by both conventional and microwave‐assisted method. A good number of analogues were evaluated for their in vitro cytotoxicity against human cervical and colon cancer cell lines by MTT protocol. Almost all the selected compounds showed remarkable cytotoxic activities. Among them, compound 4g and 4i

  从易于获得的起始前体开始，以高收率合成了一系列功能化的吡唑，异恶唑和苯并二氮杂取代的喹诺酮衍生物。这些方法可以通过常规方法和微波辅助方法合成迄今未知的具有不同取代模式的化合物。通过MTT方案评估了大量类似物对人宫颈癌和结肠癌细胞系的体外细胞毒性。几乎所有选择的化合物都显示出显着的细胞毒性活性。其中，化合物4g和4i成为最有前途的支架。这些支架将用于进一步的分子水平研究。