Anticancer, Antimicrobial and DFT Studies of Novel Synthesized Series of α-aminophosphonate Compounds Containing 3-amino-4(3H) quinazolinone moiety
Abdel-Megeed, M., Awad, M., Abdel-Aal, M., Atlam, F., Hekal, H. (2017). Anticancer, Antimicrobial and DFT Studies of Novel Synthesized Series of α-aminophosphonate Compounds Containing 3-amino-4(3H) quinazolinone moiety. EKB Journal Management System, 38(2), 194-209. doi: 10.21608/djs.2017.139453
Mohamed F. Abdel-Megeed; Mohamed K. Awad; Mahmoud F. Abdel-Aal; FatenM. Atlam; Hend A. Hekal. "Anticancer, Antimicrobial and DFT Studies of Novel Synthesized Series of α-aminophosphonate Compounds Containing 3-amino-4(3H) quinazolinone moiety". EKB Journal Management System, 38, 2, 2017, 194-209. doi: 10.21608/djs.2017.139453
Abdel-Megeed, M., Awad, M., Abdel-Aal, M., Atlam, F., Hekal, H. (2017). 'Anticancer, Antimicrobial and DFT Studies of Novel Synthesized Series of α-aminophosphonate Compounds Containing 3-amino-4(3H) quinazolinone moiety', EKB Journal Management System, 38(2), pp. 194-209. doi: 10.21608/djs.2017.139453
Abdel-Megeed, M., Awad, M., Abdel-Aal, M., Atlam, F., Hekal, H. Anticancer, Antimicrobial and DFT Studies of Novel Synthesized Series of α-aminophosphonate Compounds Containing 3-amino-4(3H) quinazolinone moiety. EKB Journal Management System, 2017; 38(2): 194-209. doi: 10.21608/djs.2017.139453

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, Page 194-209  XML PDF (1.23 MB)
Document Type: Research and Reference
DOI: 10.21608/djs.2017.139453
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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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