Design, synthesis and anticancer activity of novel pyrimidine and pyrimidine-thiadiazole hybrid glycosides

Abstract

New 1,3,4-thiadiazole thioglycosides linked to substituted pyrimidines were synthesized via glycosylation of 1,3,4-thiadiazole thiol compounds. Also, novel 1,2,3-triazole derivatives linked to carbohydrate units were prepared using the standard click chemistry conditions employing the Cu(I)-catalyzed azide-alkyne cycloaddition of substituted-aryl-azides with a selection of alkyne-functionalized sugars. The chemical structures of the new derivatives were verified using various spectroscopic techniques, such as IR, ¹H NMR, ¹³C NMR and elemental analyses. The cytotoxic activities of the prepared compounds were investigated in vitro against human liver cancer (HepG-2) and human breast adenocarcinoma (MCF7) cell lines. In addition, the biological evaluation of the new compounds involved the investigation of their effects on a human normal retinal pigmented epithelial cell line (RPE1) using the MTT assay.

Graphical Abstract

Keywords:

• 1,3,4-thiadiazole
• 1,2,3-triazole
• glycosides
• click chemistry
• MCF-7
• HepG2

Conflicts of interest

The authors declare no conflict of interest.

Additional information

Funding

The authors of this article gratefully acknowledge the Jouf University, Sakaka, Saudi Arabia, for financially support this work (project number 40/244).