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Megahed, M. Fathalla, W. Alsheikh, A. A.
Original Title
Synthesis and Antimicrobial Activity of Methyl 2-(2-(2-Arylquinazolin-4-yl)oxy) Acetylamino Alkanoates
Type
journal article in Web of Science
Language
English
Original Abstract
A series of methyl 2-(2-(2-arylquinazolin-4-yl)oxy) acetylamino alkanoate have been developed via N,N '-dicyclohexylcarbodiimide coupling of (2-arylquinazolin-4-yloxy) acetic acids with amino acid ester hydrochlorides. The O-substituted carboxylic acids were prepared by two-step reactions from the corresponding 2-arylquinazolin-4(3H)-one starting with chemoselective O-alkylation with ethyl chloroacetate and then hydrolysis of the produced esters. The reason for this O-chemoselective behavior of 2-arylquinazolin-4(3H)-one toward electrophiles was explained by theoretical density functional theory computational calculations on the model compound 2-phenylquinazolin-4(3H)-one. The antimicrobial activity of the synthesized compounds was evaluated, showing the best inhibition zone for (2-arylquinazolin-4-yloxy) acetic acids, methyl 2-(2-(2-arylquinazolin-4-yl)oxy) acetylamino acetates, and methyl 2-(2-(2-phenylquinazolin-4-yl)oxy)acetylamino-3-methylbutanoate.
Keywords
acetylamino alkanoates; antimicrobial activity
Authors
Megahed, M.; Fathalla, W.; Alsheikh, A. A.
Released
12. 11. 2018
Publisher
WILEY
Location
HOBOKEN
ISBN
0022-152X
Periodical
Journal of Heterocyclic Chemistry
Year of study
55
Number
12
State
United States of America
Pages from
2799
Pages to
2808
Pages count
10
URL
https://onlinelibrary.wiley.com/doi/pdf/10.1002/jhet.3347
BibTex
@article{BUT170477, author="Megahed, M. and Fathalla, W. and Alsheikh, A. A.", title="Synthesis and Antimicrobial Activity of Methyl 2-(2-(2-Arylquinazolin-4-yl)oxy) Acetylamino Alkanoates", journal="Journal of Heterocyclic Chemistry", year="2018", volume="55", number="12", pages="2799--2808", doi="10.1002/jhet.3347", issn="0022-152X", url="https://onlinelibrary.wiley.com/doi/pdf/10.1002/jhet.3347" }