Synthesis and Assessment of the Cytotoxic Effects of Some Novel Biginelli 3,4-Dihydropyrmidine-2-(1H) One Derivatives Containing 2-Mercapto-3-Phenyl-4(3H)-Quinazolinone

Abstract

In the present study, a new series of 3,4- dihydropyrmidine2-(1 H) one derivatives(4a-f) which linked to 2-mercapto-3-phenyl-4(3H)-quinazolinone were synthesized by using the nucleophilic substitution reaction of 2-mercapto-3-phenyl-4(3H)-quinazolinone (1) and an appropriate 6-bromomethyl-3,4- dihydropyrmidine2-(1 H) one (3a-f) in the presence of KOH as a base and in CH3CN as solvent. The chemical structures of the synthesized compounds were confirmed by means of IR, ¹H-NMR, ¹³C-NMR, Mass spectroscopy, and Elemental analysis. The cytotoxicity of the newly synthesized compounds was evaluated in vitro against the human breast cancer (MCF-7) cell line and human colon cancer cell line (HT-29) based on the results of the MTT assay. Our results indicated that compound 4b exerted the most cytotoxic effect in the two cell lines and the IC50 values were (4.25 ± 0.16 μM) for MCF-7 cell lines and (12.11 ± 0.76 μM) for HT-29 cell lines. Also, compound 4b induced apoptosis more than other compounds in the two cell lines. Therefore, compound 4b may be a potential anticancer agent.

Keywords:

• 3,4-dihydropyrmidine2-(1 H) one
• 2-mercapto-3-phenyl-4(3H)-quinazolinone
• cytotoxic effect
• MCF-7 and HT-29 cell line

Acknowledgments

We are deeply grateful to the Research Council of Urmia University for providing a fellowship for the present work.

Disclosure statement

No potential conflict of interest was reported by the author(s).

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.