Anticancer, Antimicrobial and DFT Studies of Novel Synthesized Series of α-aminophosphonate Compounds Containing 3-amino-4(3H) quinazolinone moiety | ||
| Delta Journal of Science | ||
| Article 7, Volume 38, Issue 2, December 2017, Pages 194-209 PDF (1.23 M) | ||
| Document Type: Research and Reference | ||
| DOI: 10.21608/djs.2017.139453 | ||
| Authors | ||
| Mohamed F. Abdel-Megeed; Mohamed K. Awad; Mahmoud F. Abdel-Aal; FatenM. Atlam; Hend A. Hekal | ||
| Chemistry Department, Faculty of Science, Tanta University, Tanta, Egypt | ||
| Abstract | ||
| A novel series of Diphenyl (aryl) (4-oxo-quinazolin-4(3H)-ylamino) methyl phosphonates (1-4)is obtained in high yields from the reactions of 3-amino-4(3H)-quinazolinone with different aromatic aldehydes and triphenylphosphite in the presence of cupper trifillate as a Lewis acid catalyst. The structures of the synthesized compounds are confirmed by IR, 1H NMR, and El-mass spectral data. The synthesized compounds show high antimicrobial activities against Gram-negative, Gram-positive bacteria and fungi at low concentrations (2.5-10mg/mL). Also, they show significant cytotoxicity anticancer activities against liver carcinoma cell line (HepG2). The quantum chemical calculations are performed using density functional theory (DFT), with the B3LYP hybrid functional with 6-31G + (d) basis set to study the effect of the molecular and electronic structure changes on the biological activity of the investigated compounds. The calculations show that the electron-withdrawing substituent increase the biological activity of the α-aminophosphonate compounds more than the electron donating group which is in a good agreement with the experimental results. Finally, the quantum chemical parameters confirmed with MEPs are able to describe the biological activity of the investigated compounds. | ||
| Keywords | ||
| Quinazoline derivatives; α-aminophosphonate; Anticancer activity; Antimicrobial activity; Quantum chemical parameters; DFT calculation; Computational chemistry | ||
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