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Bioactivity of Methoxylated and Methylated 1-Hydroxynaphthalene-2-Carboxanilides: Comparative Molecular Surface Analysis
H. Michnová, Š. Pospíšilová, T. Goněc, I. Kapustíková, P. Kollár, V. Kozik, R. Musioł, I. Jendrzejewska, J. Vančo, Z. Trávníček, A. Čížek, A. Bąk, J. Jampílek,
Language English Country Switzerland
Document type Comparative Study, Journal Article
Grant support
LO1305
Ministry of Education of the Czech Republic
APVV-17-0373
Slovak Research and Development Agency
APVV-17-0318
Slovak Research and Development Agency
VEGA 1/0040/17
Agency of Ministry of Education, Science, Research and Sport of the Slovak Republic
314/2019FAF
IGA VFU Brno
2018/31/B/NZ7/02122
Polish National Science Center
TH04020540
Technology Agency of the Czech Republic
NLK
Directory of Open Access Journals
from 1997
Free Medical Journals
from 1997
PubMed Central
from 2001
Europe PubMed Central
from 2001
ProQuest Central
from 1997-01-01
Open Access Digital Library
from 1997-01-01
Medline Complete (EBSCOhost)
from 2009-03-01
Health & Medicine (ProQuest)
from 1997-01-01
- MeSH
- Ampicillin pharmacology MeSH
- Principal Component Analysis MeSH
- Anilides chemical synthesis chemistry pharmacology MeSH
- Anti-Bacterial Agents chemical synthesis chemistry pharmacology MeSH
- Chloroplasts drug effects physiology MeSH
- Photosynthesis drug effects MeSH
- Isoniazid pharmacology MeSH
- Humans MeSH
- Methicillin-Resistant Staphylococcus aureus drug effects growth & development MeSH
- Methylation MeSH
- Microbial Sensitivity Tests MeSH
- Mycobacterium kansasii drug effects growth & development MeSH
- Mycobacterium tuberculosis drug effects growth & development MeSH
- Naphthols chemical synthesis chemistry pharmacology MeSH
- Spinacia oleracea chemistry drug effects metabolism MeSH
- THP-1 Cells MeSH
- Electron Transport drug effects MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Comparative Study MeSH
A series of twenty-six methoxylated and methylated N-aryl-1-hydroxynaphthalene- 2-carboxanilides was prepared and characterized as potential anti-invasive agents. The molecular structure of N-(2,5-dimethylphenyl)-1-hydroxynaphthalene-2-carboxamide as a model compound was determined by single-crystal X-ray diffraction. All the analysed compounds were tested against the reference strain Staphylococcus aureus and three clinical isolates of methicillin-resistant S.aureus as well as against Mycobacterium tuberculosis and M. kansasii. In addition, the inhibitory profile of photosynthetic electron transport in spinach (Spinacia oleracea L.) chloroplasts was specified. In vitro cytotoxicity of the most effective compounds was tested on the human monocytic leukaemia THP-1 cell line. The activities of N-(3,5-dimethylphenyl)-, N-(3-fluoro-5-methoxy-phenyl)- and N-(3,5-dimethoxyphenyl)-1-hydroxynaphthalene-2-carbox- amide were comparable with or even better than the commonly used standards ampicillin and isoniazid. All promising compounds did not show any cytotoxic effect at the concentration >30 µM. Moreover, an in silico evaluation of clogP features was performed for the entire set of the carboxamides using a range of software lipophilicity predictors, and cross-comparison with the experimentally determined lipophilicity (log k), in consensus lipophilicity estimation, was conducted as well. Principal component analysis was employed to illustrate noticeable variations with respect to the molecular lipophilicity (theoretical/experimental) and rule-of-five violations. Additionally, ligand-oriented studies for the assessment of the three-dimensional quantitative structure-activity relationship profile were carried out with the comparative molecular surface analysis to determine electron and/or steric factors that potentially contribute to the biological activities of the investigated compounds.
References provided by Crossref.org
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- $a Michnová, Hana $u Division of Biologically Active Complexes and Molecular Magnets, Regional Centre of Advanced Technologies and Materials, Faculty of Science, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic. Department of Infectious Diseases and Microbiology, Faculty of Veterinary Medicine, University of Veterinary and Pharmaceutical Sciences, Palackého třída 1/3, 61242 Brno, Czech Republic.
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- $a A series of twenty-six methoxylated and methylated N-aryl-1-hydroxynaphthalene- 2-carboxanilides was prepared and characterized as potential anti-invasive agents. The molecular structure of N-(2,5-dimethylphenyl)-1-hydroxynaphthalene-2-carboxamide as a model compound was determined by single-crystal X-ray diffraction. All the analysed compounds were tested against the reference strain Staphylococcus aureus and three clinical isolates of methicillin-resistant S.aureus as well as against Mycobacterium tuberculosis and M. kansasii. In addition, the inhibitory profile of photosynthetic electron transport in spinach (Spinacia oleracea L.) chloroplasts was specified. In vitro cytotoxicity of the most effective compounds was tested on the human monocytic leukaemia THP-1 cell line. The activities of N-(3,5-dimethylphenyl)-, N-(3-fluoro-5-methoxy-phenyl)- and N-(3,5-dimethoxyphenyl)-1-hydroxynaphthalene-2-carbox- amide were comparable with or even better than the commonly used standards ampicillin and isoniazid. All promising compounds did not show any cytotoxic effect at the concentration >30 µM. Moreover, an in silico evaluation of clogP features was performed for the entire set of the carboxamides using a range of software lipophilicity predictors, and cross-comparison with the experimentally determined lipophilicity (log k), in consensus lipophilicity estimation, was conducted as well. Principal component analysis was employed to illustrate noticeable variations with respect to the molecular lipophilicity (theoretical/experimental) and rule-of-five violations. Additionally, ligand-oriented studies for the assessment of the three-dimensional quantitative structure-activity relationship profile were carried out with the comparative molecular surface analysis to determine electron and/or steric factors that potentially contribute to the biological activities of the investigated compounds.
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