Synthesis and Antimicrobial Evaluation of 1-[(2-Substituted phenyl)carbamoyl]naphthalen-2-yl Carbamates†
AbstractSeries 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
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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.
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(9):1189.Chicago/Turabian Style
Gonec, Tomas; Pospisilova, Sarka; Holanova, Lucie; Stranik, Josef; Cernikova, Aneta; Pudelkova, Valeria; Kos, Jiri; Oravec, Michal; Kollar, Peter; Cizek, Alois; Jampilek, Josef. 2016. "Synthesis and Antimicrobial Evaluation of 1-[(2-Substituted phenyl)carbamoyl]naphthalen-2-yl Carbamates." Molecules 21, no. 9: 1189.
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