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Investigating the Spectrum of Biological Activity of Ring-Substituted Salicylanilides and Carbamoylphenylcarbamates
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
Zentiva k.s., U kabelovny 130, 102 37 Prague, Czech Republic
Department of Ecosozology and Physiotactics, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia
Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland
Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia
Department of Biological and Medical Sciences, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic
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; in revised form: 5 November 2010 / Accepted: 9 November 2010 / Published: 10 November 2010
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
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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.
Otevrel J, Mandelova Z, Pesko M, Guo J, Kralova K, Sersen F, Vejsova M, Kalinowski DS, Kovacevic Z, Coffey A, Csollei J, Richardson DR, Jampilek J. Investigating the Spectrum of Biological Activity of Ring-Substituted Salicylanilides and Carbamoylphenylcarbamates. Molecules. 2010; 15(11):8122-8142.
Otevrel, Jan; Mandelova, Zuzana; Pesko, Matus; Guo, Jiahui; Kralova, Katarina; Sersen, Frantisek; Vejsova, Marcela; Kalinowski, Danuta S.; Kovacevic, Zaklina; Coffey, Aidan; Csollei, Jozef; Richardson, Des R.; Jampilek, Josef. 2010. "Investigating the Spectrum of Biological Activity of Ring-Substituted Salicylanilides and Carbamoylphenylcarbamates." Molecules 15, no. 11: 8122-8142.