Publication detail

Synthesis and Antimicrobial Activity of Methyl 2-(2-(2-Arylquinazolin-4-yl)oxy) Acetylamino Alkanoates

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"
}