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Molecules 2010, 15(11), 8122-8142; doi:10.3390/molecules15118122
Article

Investigating the Spectrum of Biological Activity of Ring-Substituted Salicylanilides and Carbamoylphenylcarbamates

1, 1,2, 3, 4, 5, 5, 6, 7, 7, 4, 1, 7 and 1,2,*
1 Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic 2 Zentiva k.s., U kabelovny 130, 102 37 Prague, Czech Republic 3 Department of Ecosozology and Physiotactics, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia 4 Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland 5 Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia 6 Department of Biological and Medical Sciences, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic 7 Department of Pathology and Bosch Institute, University of Sydney, Sydney, New South Wales 2006, Australia
* Author to whom correspondence should be addressed.
Received: 13 August 2010 / Revised: 5 November 2010 / Accepted: 9 November 2010 / Published: 10 November 2010
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Abstract

In this study, a series of twelve ring-substituted salicylanilides and carbamoylphenylcarbamates were prepared and characterized. The compounds were analyzed using RP-HPLC to determine lipophilicity. They were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Moreover, their site of action in the photosynthetic apparatus was determined. Primary in vitro screening of the synthesized compounds was also performed against mycobacterial, bacterial and fungal strains. Several compounds showed biological activity comparable with or higher than the standards 3-(3,4-dichlorophenyl)-1,1-dimethylurea, isoniazid, penicillin G, ciprofloxacin or fluconazole. The most active compounds showed minimal anti-proliferative activity against human cells in culture, indicating they would have low cytotoxicity. For all compounds, the relationships between lipophilicity and the chemical structure are discussed.
Keywords: salicylanilides; lipophilicity; EPR study; photosynthetic electron transport inhibition; spinach chloroplasts; in vitro anti-fungal activity; in vitro anti-bacterial activity; in vitro anti-mycobacterial activity; anti-proliferative activity   salicylanilides; lipophilicity; EPR study; photosynthetic electron transport inhibition; spinach chloroplasts; in vitro anti-fungal activity; in vitro anti-bacterial activity; in vitro anti-mycobacterial activity; anti-proliferative activity  
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.

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Otevrel, J.; Mandelova, Z.; Pesko, M.; Guo, J.; Kralova, K.; Sersen, F.; Vejsova, M.; Kalinowski, D.S.; Kovacevic, Z.; Coffey, A.; Csollei, J.; Richardson, D.R.; Jampilek, J. Investigating the Spectrum of Biological Activity of Ring-Substituted Salicylanilides and Carbamoylphenylcarbamates. Molecules 2010, 15, 8122-8142.

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