(E)-3-(3-([1,1'-biphenyl]-4-yl)-3-oxoprop-1-en-1-yl)quinolin-2(1H)-one | 1415651-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-(3-([1,1'-biphenyl]-4-yl)-3-oxoprop-1-en-1-yl)quinolin-2(1H)-one
• 英文别名: NSC 755789；3-[(E)-3-oxo-3-(4-phenylphenyl)prop-1-enyl]-1H-quinolin-2-one
• CAS: 1415651-64-7
• 化学式: C₂₄H₁₇NO₂
• 分子量: 351.404
• InChiKey: YNGWVCKNUYGUPU-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  联苯单乙酮 、 1,2-二氢-2-氧代喹啉-3-甲醛 在 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以95%的产率得到(E)-3-(3-([1,1'-biphenyl]-4-yl)-3-oxoprop-1-en-1-yl)quinolin-2(1H)-one
  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

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.