Abstract
In this study, a series of twenty-two ring-substituted 2-hydroxynaphthalene-1-carboxanilides were prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium marinum, M. kasasii, M. smegmatis. and M. avium paratuberculosis. The compounds were also tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. 2-Hydroxy-N-phenylnaphthalene-1-carboxanilide and 2-hydroxy-N-(3-trifluoromethylphenyl)naphthalene-1-carboxamide (IC50 = 29 µmol/L) were the most active PET inhibitors. Some of tested compounds showed the antibacterial and antimycobacterial activity against the tested strains comparable or higher than the standards ampicillin or isoniazid. Thus, for example, 2-hydroxy-N-(3-nitrophenyl)naphthalene-1-carboxamide showed MIC = 26.0 µmol/L against methicillin-resistant S. aureus and MIC = 51.9 µmol/L against M. marinum, or 2-hydroxy-N-phenylnaphthalene-1-carboxamide demonstrated MIC = 15.2 µmol/L against M. kansasii. The structure-activity relationships for all compounds are discussed.
Disciplines
Biology
DOI
10.3390/molecules18089397
Full Publication Date
August 2013
Publisher
MDPI
Funder Name 1
Irish Department of Agrigulture, Fisheries and Food (FIRM)
Award Number 1
08RDCIT601 & 08RDCIT617
Resource Type
journal article
Access Rights
open access
License Condition
This work is licensed under a Creative Commons Attribution 4.0 International License.
Alternative Identifier
https://www.mdpi.com/1420-3049/18/8/9397
Recommended Citation
Gonec, T. et al., 2013. Antibacterial and Herbicidal Activity of Ring-Substituted 2-Hydroxynaphthalene-1-carboxanilides. Molecules, 18(8), pp.9397–9419. Available at: http://dx.doi.org/10.3390/molecules18089397.
Publication Details
Molecules
Copyright © Gonec, T. et al.
This study was supported by the IGA VFU Brno 96/2012/FaF and 65/2012/FVL, the Slovak Grant Agency VEGA, Grant No. 1/0612/11, by the Project APVV-0061-11, by Sanofi-Aventis Pharma Slovakia, by the project CEITEC (Central European Institute of Technology), Reg. No. CZ.1.05/1.1.00/02.0068 from the European Regional Development Fund and by the Irish Department of Agriculture Fisheries and Food (FIRM): Refs 08RDCIT601 & 08RDCIT617.