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HERO ID
3036105
Reference Type
Journal Article
Title
Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides
Author(s)
Gonec, T; Zadrazilova, I; Nevin, E; Kauerova, T; Pesko, M; Kos, J; Oravec, M; Kollar, P; Coffey, A; O'Mahony, J; Cizek, A; Kralova, K; Jampilek, J
Year
2015
Is Peer Reviewed?
1
Journal
Molecules
ISSN:
1420-3049
Volume
20
Issue
6
Page Numbers
9767-9787
Language
English
PMID
26023938
DOI
10.3390/molecules20069767
Web of Science Id
WOS:000357992700018
URL
https://www.scopus.com/inward/record.uri?eid=2-s2.0-84938352696&doi=10.3390%2fmolecules20069767&partnerID=40&md5=27befa005502fb7a592734f030f08f99
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Abstract
A series of fifteen new N-alkoxyphenylanilides of 3-hydroxynaphthalene-2-carboxylic acid was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra and M. avium subsp. paratuberculosis. Some of the tested compounds showed antibacterial and antimycobacterial activity against the tested strains comparable with or higher than that of the standards ampicillin or rifampicin. 3-Hydroxy-N-(2-propoxyphenyl)naphthalene-2-carboxamide and N-[2-(but-2-yloxy)-phenyl]-3-hydroxynaphthalene-2-carboxamide had MIC = 12 µM against all methicillin-resistant S. aureus strains; thus their activity is 4-fold higher than that of ampicillin. The second mentioned compound as well as 3-hydroxy-N-[3-(prop-2-yloxy)phenyl]-naphthalene-2-carboxamide had MICs = 23 µM and 24 µM against M. tuberculosis respectively. N-[2-(But-2-yloxy)phenyl]-3-hydroxynaphthalene-2-carboxamide demonstrated higher activity against M. avium subsp. paratuberculosis than rifampicin. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using THP-1 cells, and no significant lethal effect was observed for the most potent compounds. The compounds were additionally tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3-Ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 4.5 µM) was the most active PET inhibitor. The structure-activity relationships are discussed.
Keywords
Chemistry--Organic Chemistry
Tags
IRIS
•
Naphthalene
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•
Naphthalene (2021 Evidence mapping publication)
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New Nov 2015 (private)
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