Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides
Tomas Gonec,
Jiri Kos,
Eoghan Nevin,
Rodney Govender,
Matus Pesko,
Jan Tengler,
Ivan Kushkevych,
Vendula Stastna,
Michal Oravec,
Peter Kollar,
Jim O'Mahony,
Katarina Kralova,
Aidan Coffey,
Josef Jampilek
Affiliations
Tomas Gonec
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
Jiri Kos
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
Eoghan Nevin
Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland
Rodney Govender
Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland
Matus Pesko
Department of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia
Jan Tengler
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
Ivan Kushkevych
Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
Vendula Stastna
Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
Michal Oravec
Global Change Research Centre AS CR, Belidla 986/4a, 60300 Brno, Czech Republic
Peter Kollar
Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
Jim O'Mahony
Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland
Katarina Kralova
Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia
Aidan Coffey
Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland
Josef Jampilek
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
In this study, a series of twenty-two ring-substituted naphthalene-1-carboxanilides were prepared and characterized. Primary in vitro screening of the synthesized carboxanilides was performed against Mycobacterium avium subsp. paratuberculosis. N-(2-Methoxyphenyl)naphthalene-1-carboxamide, N-(3-methoxy-phenyl)naphthalene-1-carboxamide, N-(3-methylphenyl)naphthalene-1-carboxamide, N-(4-methylphenyl)naphthalene-1-carboxamide and N-(3-fluorophenyl)naphthalene-1-carboxamide showed against M. avium subsp. paratuberculosis two-fold higher activity than rifampicin and three-fold higher activity than ciprofloxacin. The most effective antimycobacterial compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. The testing of biological activity of the compounds was completed with the study of photosynthetic electron transport (PET) inhibition in isolated spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibiting activity expressed by IC50 value of the most active compound N-[4-(trifluoromethyl)phenyl]naphthalene-1-carboxamide was 59 μmol/L. The structure-activity relationships are discussed.
