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

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

Jan Otevrel 1 , Zuzana Mandelova 1,2 , Matus Pesko 3 , Jiahui Guo 4 , Katarina Kralova 5 , Frantisek Sersen 5 , Marcela Vejsova 6 , Danuta S. Kalinowski 7 , Zaklina Kovacevic 7 , Aidan Coffey 4 , Jozef Csollei 1 , Des R. Richardson 7  and Josef Jampilek 1,2,* email
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; in revised form: 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  

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Cite This Article

MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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