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

• Published in: Polycyclic aromatic compounds 2024-03, Vol.44 (3), p.1781-1792
• Main Authors: Nouri, Mojtaba, Pirmohammadi, Nasim, Dilmaghani, Karim A., Pazhang, Yaghub
• Format: Article
• Language: English
• Subjects: 2-mercapto-3-phenyl-4(3H)-quinazolinone; 3,4-dihydropyrmidine2-(1 H) one; Anticancer properties; Antineoplastic drugs; Apoptosis; Chemical analysis; Chemical synthesis; Colon cancer; cytotoxic effect; Cytotoxicity; Mass spectroscopy; MCF-7 and HT-29 cell line; NMR; Nuclear magnetic resonance; Quinazolinone; Quinazolinones; Substitution reactions
• ISSN: 1040-6638; 1563-5333
• DOI: 10.1080/10406638.2023.2206670

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, 1 H-NMR, 13 C-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.