Synthesis of new series of quinazolinone derivatives endowed with anticancer potential | ||
| Benha Journal of Applied Sciences | ||
| Articles in Press, Accepted Manuscript, Available Online from 13 March 2023 | ||
| Document Type: Original Research Papers | ||
| DOI: 10.21608/bjas.2023.188176.1037 | ||
| Author | ||
| Mohga Abdelsalam Ewais* | ||
| Chemistry, faculty of science, benha university, benha, egypt | ||
| Abstract | ||
| The key structure 2-phenylbenzoxazinone 1 was utilised to produce innovative series of N-containing heterocyclic compounds. Hydrazinolysis of 2-phenylbenzoxazinone 1 under standard circumstances generated the matching 3-amino quinazolinone derivative 2, which was employed as the main structure in our investigation. Cyanuric chloride was attacked nucleophilically by the synthesised quinazolinone 2 to produce the monosubstituted 1,3,5-triazine derivative 3-((4,6-dichloro-1,3,5-triazin-2-yl)amino). -2-phenyl-2,3-dihydroquinazolin-4(4aH)-one 8 In addition, the nucleophilic replacement of monosubstituted 1,3,5-triazine with various amino acids led to the formation of di- and tri-substituted 1,3,5-triazine derivatives, depending on the temperature and molar ratio of the amino acids utilised. Hydrazinolysis of 2-phenylbenzoxazinone 1 under microwave irradiation produced the hydrazino benzamide derivative 7, which, following condensation with various aromatic aldehydes, supplied distinct hydrazones 14a-e. Schiff's bases 14a, 14b, and 14d exhibited outstanding anticancer activities with single-digit nanomolar IC50 values against triple negative breast cancer cells; MDA-MB 231 being more potent than doxorubicin and all the evaluated new compounds and precursors in the present study. In addition, this observation's safety profile seemed encouraging. ((4-chloro-6-((4-oxo-2-phenyl-4,4a-dihydroquinazolin-3(2H)-yl)amino)-1,3,5-triazin-2-yl)amino) The IC50 values against MDA-MB 231 indicated that acids 11a and 11b had somewhat less significant anticancer activity. In contrast, compounds 11a, 12a, 12b, and 14 a-d were more effective than doxorubicin against HepG-2b liver cancer cells. | ||
| Keywords | ||
| Triazine; Quinazoline; Anticancer | ||
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