Design and synthesis of tetrahydropyrimidinone(thione)-triazole hybrid scaffolds and evaluation of their biological activities

Abstract

In this study, we designed and synthesized some new tetrahydropyrimidinone(thione)-triazole hybrid derivatives by click and one-pot Biginelli reactions. FT IR, ¹H NMR, and ¹³C NMR spectra and mass spectrometry, and elemental analysis were used to determine the structures of the derivatives. The cytotoxic and antimicrobial activities of these derivatives were evaluated against three cancer cell lines and two bacterial strains. Among all, benzyl 4-(4-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine (THPM)-5-carboxylate (9f) revealed the highest cytotoxic activity against MCF7 and Hep-G2 cell lines. However, none of the derivatives display cytotoxic activity against A549 cell line. In addition, compounds methyl 4-(4-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-6-methyl-2-thioxo-1,2,3,4- THPM-5-carboxylate (9d) and ethyl 4-(4-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-6-methyl-2-thioxo-1,2,3,4- THPM-5-carboxylate (9e) were found to exhibit potent activity compared to other compounds and the standard drugs against two bacterial strains.

Graphical Abstract

Keywords:

• Click reaction
• neoplasm
• dihydropyrimidine
• anti-bacterial
• hybrid

Disclosure statement

The authors declare no conflict of interest.

Funding

This work was supported by the Ardabil University of Medical Sciences under Grant IR.ARUMS.REC.1398.269.

Additional information

Funding

This work was supported by the Ardabil University of Medical Sciences under Grant IR.ARUMS.REC.1398.269.