(E)-3-(2-hydroxyquinolin-3-yl)-1-(4-methoxyphenyl) prop-2-en-1-one

• 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: (E)-3-(2-hydroxyquinolin-3-yl)-1-(4-methoxyphenyl) prop-2-en-1-one
• 英文别名: 3-[(E)-3-(4-methoxyphenyl)-3-oxoprop-1-enyl]-1H-quinolin-2-one
• 化学式: C₁₉H₁₅NO₃
• 分子量: 305.333
• InChiKey: WJDJGOPDWCIUCV-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 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：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-hydroxyquinolin-3-yl)-1-(4-methoxyphenyl) prop-2-en-1-one 、 氨基硫脲 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以84%的产率得到3-(4-methoxyphenyl)-5-(2-oxo-1,2-dihydroquinolin-3-yl)-4,5-dihydropyrazolo-1-carbothioamide
  参考文献：
  名称：

  Synthesis of novel quinoline-2-one based chalcones of potential anti-tumor activity

  摘要：

  Novel quinoline-2-one based chalcones were synthesized from a Claisen-Schmidt condensation by using the couple KOH/1,4-dioxane as reaction medium. A relatively stable aldol was isolated and identified as the intermediate species in the formation of the target chalcones. Nine of the obtained compounds were in vitro screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Products 16c, 16d, 16h and 27 exhibited the highest activity, being compound 27 the most active, displaying remarkable activity against 50 human tumor cell lines, thirteen of them with GI(50) values <= 1.0 mu M, being the HCT-116 (Colon, GI(50) = 0.131 mu M) and LOX IMVI (Melanoma, GI(50) = 0.134 mu M) the most sensitive strains. Compound 27 was referred to in vivo acute toxicity and hollow fiber assay by the Biological Evaluation Committee of the NCI. The acute toxicity study indicated that compound 27 was well tolerated intraperitoneally (150 mg/kg/dose) by athymic nude mice. This compound may possibly be used as lead compound for developing new anticancer agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.039
• 作为产物：
  描述：

  (E)-1-(4-methoxyphenyl)-3-(2-methoxyquinolin-3-yl)prop-2-en-1-one 在 盐酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以92 %的产率得到(E)-3-(2-hydroxyquinolin-3-yl)-1-(4-methoxyphenyl) prop-2-en-1-one
  参考文献：
  名称：

  新型3-(喹啉-3-基)-1-苯基丙-2-en-1-酮衍生物的设计、合成、抗结核活性和计算研究

  摘要：

  结核病 (TB) 是一种由结核分枝杆菌( Mtb ) 引起的传染性疾病，影响着全球人民。喹啉和查耳酮核心具有良好的抗结核性能；因此，我们设计了一种含有喹啉和查耳酮的混合支架。通过亲核取代、Vilsmeier Haack甲酰化、Claisen Schmidt缩合等不同反应合成了一系列3-(喹啉-3-基)-1-苯基丙-2-en-1-one类似物7a-p和8a-k。去甲基化。光谱方法，包括1 H NMR、 13 C NMR、IR 和 HRMS，用于表征所有合成的化合物。评估化合物7a-p和8a-k针对Mtb H 37 Rv (ATCC 27294)的抗结核活性。这些化合物在 6.25–50 μM 范围内表现出针对 H 37 Rv 的抗结核活性。瑞士 ADME 的计算机计算研究表明 ADME 参数更好，并且具有良好的药代动力学特征。在本研究中，化合物8a、7a和7p对Mtb H37Rv 显示出最有潜力的抗结核活性，MIC

  DOI：

  10.1007/s00044-024-03295-z

文献信息

• Synthesis of novel quinoline-2-one based chalcones of potential anti-tumor activity
  作者：Rodrigo Abonia、Daniel Insuasty、Juan Castillo、Braulio Insuasty、Jairo Quiroga、Manuel Nogueras、Justo Cobo

  DOI：10.1016/j.ejmech.2012.08.039

  日期：2012.11

  Novel quinoline-2-one based chalcones were synthesized from a Claisen-Schmidt condensation by using the couple KOH/1,4-dioxane as reaction medium. A relatively stable aldol was isolated and identified as the intermediate species in the formation of the target chalcones. Nine of the obtained compounds were in vitro screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Products 16c, 16d, 16h and 27 exhibited the highest activity, being compound 27 the most active, displaying remarkable activity against 50 human tumor cell lines, thirteen of them with GI(50) values <= 1.0 mu M, being the HCT-116 (Colon, GI(50) = 0.131 mu M) and LOX IMVI (Melanoma, GI(50) = 0.134 mu M) the most sensitive strains. Compound 27 was referred to in vivo acute toxicity and hollow fiber assay by the Biological Evaluation Committee of the NCI. The acute toxicity study indicated that compound 27 was well tolerated intraperitoneally (150 mg/kg/dose) by athymic nude mice. This compound may possibly be used as lead compound for developing new anticancer agents. (C) 2012 Elsevier Masson SAS. All rights reserved.