6-(4-bromophenyl)-4-(3,4-dimethoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile | 1240387-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(4-bromophenyl)-4-(3,4-dimethoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 6-(4-bromophenyl)-1,2-dihydro-4-(3,4-dimethoxyphenyl)-2-oxopyridine-3-carbonitrile
• CAS: 1240387-82-9
• 化学式: C₂₀H₁₅BrN₂O₃
• 分子量: 411.255
• InChiKey: ZBGSENICDDLEKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  300 °C(Solvent: Ethanol; Dimethylformamide)
• 沸点：
  593.7±50.0 °C(predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  6-(4-bromophenyl)-4-(3,4-dimethoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile 在 一水合肼 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 6-(4-bromophenyl)-4-(3,4-dimethoxyphenyl)-1H-pyrazolo[3,4-b]pyridin-3-amine
  参考文献：
  名称：

  Multi-targeted anti-Alzheimer's agents: Synthesis, biological evaluation, and molecular modeling study of some pyrazolopyridine hybrids

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115880
• 作为产物：
  描述：

  4-溴苯乙酮 、 3,4-二甲氧基苯甲醛 、 氰乙酸乙酯 在 ammonium acetate 作用下， 以 polyethylene glycol-600 为溶剂， 反应 4.0h， 以67%的产率得到6-(4-bromophenyl)-4-(3,4-dimethoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  One-Pot Four Component Synthesis of 4, 6-Disubstituted 3-Cyano-2- Pyridones in Polyethylene Glycol

  摘要：

  报告了酮、醛、氰乙酸乙酯和乙酸铵在聚乙二醇-600 中的反应。在没有催化剂的情况下，反应顺利进行，生成 2-吡啶酮。

  DOI：

  10.2174/157017810791514832

文献信息

• <p>Design, Synthesis, And Evaluation Of Cyanopyridines As Anti-Colorectal Cancer Agents Via Inhibiting STAT3 Pathway</p>
  作者：Lingyuan Xu、Lingxi Shi、Sensen Qiu、Siyu Chen、Mengsha Lin、Youqun Xiang、Chengguang Zhao、Jiandong Zhu、Liqun Shen、Zhigui Zuo

  DOI：10.2147/dddt.s217800

  日期：——

  Background: Colorectal cancer is one of the common malignant tumors. Cyanopyridine and aminocyanopyridine having a carbon-nitrogen bond have been shown to have significant anticancer effects. STAT3 is a promising therapeutic target in multiple cancers. However, there are currently no effective STAT3 inhibitors in clinical practice for the treatment of colorectal cancer.Materials and methods: We screened 27 cyanopyridines for their anticancer activity by cell viability. The HCT-116, RKO, and DLD-1 cell lines were used to evaluate the anti-colorectal cancer effect of 3n. Scratch experiments and colony formation assays were used for the assessment of cell migration and proliferation capacity. Phosphorylated STAT3, STAT3, MCL-1, and Survivin levels were assessed by Western blot analysis.Results: In this study, we synthesized 27 cyanopyridines and screened their anticancer activities in three human tumor cells, HCT-116, Hela229, and A375. We found that 2-amino-3-cyanopyridine 3n has better anticancer activity with IC50 values in the low micromolar range. Furthermore, 3n significantly inhibited the migration and colony formation of colorectal cancer cells. Mechanistically, 3n inhibited the expression of STAT3 phosphorylation in a dose- and time-dependent manner.Conclusion: 3n is worth of further investigations toward the discovery of STAT3 inhibitor as a drug candidate for cancer therapy.