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Molecules 2016, 21(9), 1189; doi:10.3390/molecules21091189

Synthesis and Antimicrobial Evaluation of 1-[(2-Substituted phenyl)carbamoyl]naphthalen-2-yl Carbamates

1
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, Brno 61242, Czech Republic
2
Department of Infectious Diseases and Microbiology, Faculty of Veterinary Medicine, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, Brno 61242, Czech Republic
3
Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, Brno 61242, Czech Republic
4
Global Change Research Institute CAS, Belidla 986/4a, Brno 60300, Czech Republic
5
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, Bratislava 83232, Slovakia
Preliminary Results Were Presented at the 8th Central European Conference “Chemistry towards Biology” (CTB-2016), Brno, Czech Republic, 28 August–1 September 2016 (Paper P-18).
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 24 August 2016 / Revised: 2 September 2016 / Accepted: 5 September 2016 / Published: 7 September 2016
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Abstract

Series of thirteen 1-[(2-chlorophenyl)carbamoyl]naphthalen-2-yl carbamates and thirteen 1-[(2-nitrophenyl)carbamoyl]naphthalen-2-yl carbamates with alkyl/cycloalkyl/arylalkyl chains were prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, two methicillin-resistant S. aureus strains, Mycobacterium marinum, and M. kansasii. 1-[(2-Chlorophenyl)carbamoyl]naphthalen-2-yl ethylcarbamate and 1-[(2-nitrophenyl)carbamoyl]naphthalen-2-yl ethylcarbamate showed antistaphylococcal (MICs = 42 µM against MRSA) and antimycobacterial (MICs = 21 µM) activity against the tested strains comparable with or higher than that of the standards ampicillin and isoniazid. In the case of bulkier carbamate tails (R > propyl/isopropyl), the activity was similar (MICs ca. 70 µM). Screening of the cytotoxicity of both of the most effective compounds was performed using THP-1 cells, and no significant lethal effect was observed (LD50 >30 µM). The structure-activity relationships are discussed. View Full-Text
Keywords: carbamates; hydroxynaphthalene-carboxamides; in vitro antibacterial activity; in vitro antimycobacterial activity; in vitro cytotoxicity assay; structure-activity relationships carbamates; hydroxynaphthalene-carboxamides; in vitro antibacterial activity; in vitro antimycobacterial activity; in vitro cytotoxicity assay; structure-activity relationships
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Gonec, T.; Pospisilova, S.; Holanova, L.; Stranik, J.; Cernikova, A.; Pudelkova, V.; Kos, J.; Oravec, M.; Kollar, P.; Cizek, A.; Jampilek, J. Synthesis and Antimicrobial Evaluation of 1-[(2-Substituted phenyl)carbamoyl]naphthalen-2-yl Carbamates. Molecules 2016, 21, 1189.

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