Anticancer, Antimicrobial and DFT Studies of Novel Synthesized Series of α-aminophosphonate Compounds Containing 3-amino-4(3H) quinazolinone moiety

Document Type : Research and Reference

Authors

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

Delta Journal of Science
Volume 38, Issue 2
December 2017
Pages 194-209

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