Synthesis and biological evaluation of selenopyrimidine derivatives bearing thiazolyl moiety

Abstract

The aim of this study is to explain how new thiazole and selenophene moieties were obtained from 2-amino-4-(4-methylthiazol-2-yl)selenophene-3-carbonitrile (3) and to assess the antioxidant and cytotoxic properties of these new compounds. Compound 3 is prepared and subjected to react with each of CS2, malononitrile in EtOH/TEA, ECA, a mixture of HCl and AcOH, formamide, formic acid, malononitrile in the presence of EtONa to give their corresponding selenopyrimidine and selenopyridine derivatives 4–10. Moreover, compound 3 reacted with thiourea, hydrazine hydrate, CS2 in NaOH/DMF, and phenyl isothiocyanate to afford selenolo[2,3-d]pyrimidines 11–17 and related compounds. The recently synthesized compounds were tested for their DPPH radical scavenging and cytotoxic properties against the HePG-2 and MCF-7 cell lines. Compounds 5 and 11 demonstrated potential radical scavenging activity, but compounds 5 and 6 exhibited the strongest cytotoxic action against the examined cell lines. According to molecular docking data, the compounds under research are intriguing candidates for the development of new anticancer therapeutic targets.

Keywords

• Thiazole
• Pyrimidine
• Pyridine
• Antioxidant
• Cytotoxic activity