1-(4-aminophenyl)-3-(4-cyanophenyl)prop-2-en-1-one | 25870-76-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(4-aminophenyl)-3-(4-cyanophenyl)prop-2-en-1-one
• 英文别名: 4-[(E)-3-(4-aminophenyl)-3-oxoprop-1-enyl]benzonitrile
• CAS: 25870-76-2
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: XGLUXNHFMGBZIH-BJMVGYQFSA-N

物化性质

• 熔点：
  153-154 °C
• 沸点：
  501.8±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.88
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-氨基苯乙酮 、 4-氰基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以47%的产率得到1-(4-aminophenyl)-3-(4-cyanophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Fluorescentα,β-Unsaturated Carbonyl Compounds and 2-Methylpyridines. Their Application to a Quantitative Analysis of Carnitine

  摘要：

  α，β-不饱和羰基化合物和含有4-（二烷基氨基）苯基取代基的2-甲基吡啶可以作为肉碱定量分析的荧光标记试剂。在合成的试剂中，6-（4-氨基苯基）-3-氰基-4-[4-（二乙基氨基）苯基]-2-甲基吡啶表现出最佳性能。

  DOI：

  10.1246/bcsj.69.2961

文献信息

• Fluorescent<i>α</i>,<i>β</i>-Unsaturated Carbonyl Compounds and 2-Methylpyridines. Their Application to a Quantitative Analysis of Carnitine
  作者：Ken-ichi Nakaya、Kazumasa Funabiki、Katsuyoshi Shibata、Hiroshige Muramatsu、Masaki Matsui

  DOI：10.1246/bcsj.69.2961

  日期：1996.10

  α,β-Unsaturated carbonyl compounds and 2-methylpyridines containing a 4-(dialkylamino)phenyl substituent can be used as fluorescent labeling reagents for the quantitative analysis of carnitine. 6-(4-Aminophenyl)-3-cyano-4-[4-(diethylamino)phenyl]-2-methylpyridine showed the best properties among the synthesized reagents.

  α，β-不饱和羰基化合物和含有4-（二烷基氨基）苯基取代基的2-甲基吡啶可以作为肉碱定量分析的荧光标记试剂。在合成的试剂中，6-（4-氨基苯基）-3-氰基-4-[4-（二乙基氨基）苯基]-2-甲基吡啶表现出最佳性能。
• Yi, Fengping; Peng, Yanqing; Song, Gonghua, Journal of Chemical Research, <hi>2005</hi>, # 5, p. 311 - 312
  作者：Yi, Fengping、Peng, Yanqing、Song, Gonghua、Li, Jizong

  DOI：——

  日期：——
• Antiproliferative activity and p53 upregulation effects of chalcones on human breast cancer cells
  作者：Mariana Bastos dos Santos、Daiane Bertholin Anselmo、Jéssica Gisleine de Oliveira、Bruna V. Jardim-Perassi、Diego Alves Monteiro、Gabriel Silva、Eleni Gomes、Ana Lucia Fachin、Mozart Marins、Débora Aparecida Pires de Campos Zuccari、Luis Octavio Regasini

  DOI：10.1080/14756366.2019.1615485

  日期：2019.1.1

  Chalcones are valuable structures for drug discovery due to their broad bioactivity spectrum. In this study, we evaluated 20 synthetic chalcones against estrogen-receptor-positive breast cancer cells (MCF-7 line) and triple-negative breast cancer (TNBC) cells (MDA-MB-231 line). Antiproliferative screening by MTT assay resulted in two most active compounds: 2-fluoro-4'-aminochalcone (11) and 3-pyridyl-4'-aminochalcone (17). Their IC50 values ranged from 13.2 to 34.7 mu M against both cell lines. Selected chalcones are weak basic compounds and maintained their antiproliferative activity under acidosis conditions (pH 6.7), indicating their resistance to ion-trapping effect. The mode of breast cancer cells death was investigated and chalcones 11 and 17 were able to induce apoptosis rather than necrosis in both lines. Antiproliferative target investigations with MCF-7 cells suggested 11 and 17 upregulated p53 protein expression and did not affect Sp1 protein expression. Future studies on chalcones 11 and 17 can define their in vivo therapeutic potential.