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. 2016 Sep 7;21(9):1189.
doi: 10.3390/molecules21091189.

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

Tomas Gonec  1 , Sarka Pospisilova  2 , Lucie Holanova  3 , Josef Stranik  4 , Aneta Cernikova  5 , Valeria Pudelkova  6 , Jiri Kos  7 , Michal Oravec  8 , Peter Kollar  9 , Alois Cizek  10 , Josef Jampilek  11
Affiliations

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

Tomas Gonec et al. Molecules. .

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.

Keywords: carbamates; hydroxynaphthalene-carboxamides; in vitro antibacterial activity; in vitro antimycobacterial activity; in vitro cytotoxicity assay; structure-activity relationships.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis of 1-[(2-chlorophenyl)carbamoyl]naphthalen-2-yl carbamates 3–15 and 1-[(2-nitrophenyl)carbamoyl]naphthalen-2-yl carbamates 16–28. Reagents and conditions: (a) PCl3, chlorobenzene, MW; (b) TEA, acetonitrile, ambient temperature.
Figure 1
Figure 1
Dependence of the in vitro antimycobacterial activity against M. kansasii DSM 44162 log (1/MIC [M]) of the tested compounds on lipophilicity, expressed as log P (A) and bulkiness/molar volume (MV [cm3]) of individual R2 substituents (B).
Figure 2
Figure 2
Increase of the general antimicrobial activity owing to the R2 substituent in dependence on the electronic properties are expressed as electronic constants σ*.
See this image and copyright information in PMC

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