Microwave synthesis, anti-oxidant and anti-tumor activity of some nucleosides derived 2-oxonicotinonitrile

Abstract

A facile and convenient synthesis of novel cyclic and acyclic nucleoside derivatives incorporating 2-oxo-1,2-dihydropyridine-3-carbonitrile moiety has been described. The aglycons 3a,b were coupled with different activated halosugars such as glucosyl, galactosyl, lactosyl bromides and peracetylated ribose, in addition to, acyclic sugar as 4-bromobutylacetate and 2-acetoxyethoxymethyl bromide in basic medium under conventional and microwave irradiation. Deprotection of the synthesized nucleosides was obtained in presence of Et₃N/MeOH and few drops of water. The structures of the synthesized compounds have been deduced from their elemental analyses and spectral data (IR, ¹H NMR, and ¹³C NMR). Some of the synthesized compounds were screened as antioxidant and anticancer agents. Good and moderate anticancer activities against HepG-2, PC-3 and HCT116 were observed in vitro for some compounds.

GRAPHICAL ABSTRACT

Keywords:

• Acyclic sugars
• anti-cancer activity
• anti-oxidant
• halosugars
• nucleosides
• pyridin-2-(1H)-one-3-carbonitriles

Acknowledgments

The authors thank the organic chemistry labor at Zagazig University for making our research, authors are also grateful to the staff of the Antitumor Laboratory, National Research Center, Cairo, Egypt and the staff of the Regional Center for Mycology & Biotechnology, Al-Azhar University (Cairo, Egypt).