Green synthesis of 2-amino-3-cyanopyridines via a cooperative vinylogous anomeric-based oxidation and their antiproliferative effects on liver, breast, and prostate cancer studies

Abstract

2-Amino-3-cyanopyridine derivatives were synthesized in an ultrasonic bath and one pot four-component reactions with high yields, in a short time, without solvent and catalyst, and anticancer activity studies on MCF7, DU145, and HepG2 cell lines were investigated. 18 compounds were synthesized in 4–25 min time interval and 85–99% yield. Among these compounds, the IC50 values in 7a, 6a, and 3a on MCF7 breast cancer cell line was found to be 1.80, 1.95, and 2.50 µM, respectively, while the values in the HepG2 liver cancer cell line were 7.71, 7.90, and 8.05 µM, respectively. In studies conducted in the DU145 prostate cancer cell line, IC50 values of compounds 1b, 2b, and 8b were found to be 9.90, 10.10, and 15.30 µM, respectively.

Graphical Abstract

Keywords:

• Aminocyanopyridine
• ultrasonic irradiation
• multicomponent reaction
• heterocycles
• anticancer activity
• prostate cancer
• breast cancer
• liver cancer

Acknowledgements

The authors are greatly thankful to the Scientific and Technical Research Council of Turkey (TUBITAK) for a scholarship to Mehmet Erşatır.

Disclosure statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this article.

Scheme 1. A plausible mechanistic pathway for the synthesis of 2-amino-4,6 diphenylnicotinonitrile via a cooperative vinylogous anomeric-based oxidation reaction.

Data availability statement

The authors confirm that the data supporting the findings of this study are available within the article [and/or] its supplementary materials.