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ORIGINAL ARTICLE
Year : 2019  |  Volume : 14  |  Issue : 3  |  Page : 247-254

Synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3


1 Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Science, Isfahan University of Medical Sciences, Isfahan, I.R. Iran
2 Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Science; Isfahan Pharmaceutical Sciences Research Center, School of Pharmacy and Pharmaceutical Science, Isfahan University of Medical Sciences, Isfahan, I.R. Iran
3 Isfahan Pharmaceutical Sciences Research Center, School of Pharmacy and Pharmaceutical Science, Isfahan University of Medical Sciences, Isfahan, I.R. Iran
4 Physiology Research Center, Isfahan University of Medical Sciences, Isfahan, I.R. Iran

Correspondence Address:
Ghadamali Khodarahmi
Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Science; Isfahan Pharmaceutical Sciences Research Center, School of Pharmacy and Pharmaceutical Science, Isfahan University of Medical Sciences, Isfahan
I.R. Iran
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Source of Support: None, Conflict of Interest: None


DOI: 10.4103/1735-5362.258493

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Quinazolinone and benzimidazole are both fused heterocyclic compounds which have shown valuable biological properties including cytotoxic, antibacterial, and antifungal activities. In this study, a series of novel quinazolinone derivatives substituted with benzimidazole were synthesized in two parts. In the first part 2 - phenyl - 1H - benzimidazol - 6 - amine (4) was synthesized from the reaction of 4-nitro-o-phenylenediamine and benzoic acid. In the second part, new 3-(2-phenyl-1H benzoimidazol-5-yl)- 3H-quinazolin-4-one derivatives (8a-8f) were also prepared. Finally compound 4 was reacted with the different benzoxazinone derivatives (8a-8f) to give the target compounds. The structures of the synthesized compounds were confirmed by IR and 1HNMR. Cytotoxic activities of the final compounds were assessed at 100, 200, 300, 400, and 500 μM against MCF-7 and HeLa cell lines using the MTT colorimetric assay. Almost all compounds exhibited good cytotoxic activity against both cell lines. Compound 9d demonstrated the highest cytotoxic activity against MCF7 and Hela cell lines with IC50 70 μM and 50 μM, respectively.


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