Synthesis and Antimicrobial Activity of Methyl 2-(2-(2-Arylquinazolin-4-yl)oxy) Acetylamino Alkanoates
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216305%3A26310%2F18%3APU140122" target="_blank" >RIV/00216305:26310/18:PU140122 - isvavai.cz</a>
Result on the web
<a href="https://onlinelibrary.wiley.com/doi/pdf/10.1002/jhet.3347" target="_blank" >https://onlinelibrary.wiley.com/doi/pdf/10.1002/jhet.3347</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/jhet.3347" target="_blank" >10.1002/jhet.3347</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis and Antimicrobial Activity of Methyl 2-(2-(2-Arylquinazolin-4-yl)oxy) Acetylamino Alkanoates
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/LO1211" target="_blank" >LO1211: Materials Research Centre at FCH BUT- Sustainability and Development</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Heterocyclic Chemistry
ISSN
0022-152X
e-ISSN
1943-5193
Volume of the periodical
55
Issue of the periodical within the volume
12
Country of publishing house
US - UNITED STATES
Number of pages
10
Pages from-to
2799-2808
UT code for WoS article
000453457300016
EID of the result in the Scopus database
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