Ring-substituted 4-Hydroxy-1H-quinolin-2-ones: Preparation and Biological Activity

doi:10.3390/molecules14031145

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Molecules 2009, 14(3), 1145-1159; doi:10.3390/molecules14031145

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Ring-substituted 4-Hydroxy-1H-quinolin-2-ones: Preparation and Biological Activity

Josef Jampilek^{1, 2,}* , Robert Musiol³, Matus Pesko⁴, Katarina Kralova⁴, Marcela Vejsova⁵, James Carroll⁶, Aidan Coffey⁶, Jacek Finster³, Dominik Tabak³, Halina Niedbala³, Violetta Kozik³, Jaroslaw Polanski³, Jozef Csollei² and Jiri Dohnal^{1, 2}

¹ Zentiva k.s., U kabelovny 130, 102 37 Prague 10, Czech Republic ² Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic ³ Institute of Chemistry, University of Silesia, Szkolna 9, 40007 Katowice, Poland ⁴ Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia ⁵ Department of Biological and Medical Sciences, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic ⁶ Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland

* Author to whom correspondence should be addressed.

Received: 4 February 2009; in revised form: 3 March 2009 / Accepted: 11 March 2009 / Published: 13 March 2009

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Abstract: In the study, a series of twelve ring-substituted 4-hydroxy-1H-quinolin-2-one derivatives were prepared. The procedures for synthesis of the compounds are presented. The compounds were analyzed using RP-HPLC to determine lipophilicity and tested for their photosynthesis-inhibiting activity using spinach (Spinacia oleracea L.) chloroplasts. All the synthesized compounds were also evaluated for antifungal activity using in vitro screening with eight fungal strains. For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds are discussed, as well as their structure-activity relationships (SAR).

Keywords: Quinolinone derivatives; Lipophilicity; OER inhibition; Spinach chloroplasts; In vitro antifungal activity; Structure-activity relationships

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MDPI and ACS Style

Jampilek, J.; Musiol, R.; Pesko, M.; Kralova, K.; Vejsova, M.; Carroll, J.; Coffey, A.; Finster, J.; Tabak, D.; Niedbala, H.; Kozik, V.; Polanski, J.; Csollei, J.; Dohnal, J. Ring-substituted 4-Hydroxy-1H-quinolin-2-ones: Preparation and Biological Activity. Molecules 2009, 14, 1145-1159.

AMA Style

Jampilek J., Musiol R., Pesko M., Kralova K., Vejsova M., Carroll J., Coffey A., Finster J., Tabak D., Niedbala H., Kozik V., Polanski J., Csollei J., Dohnal J. Ring-substituted 4-Hydroxy-1H-quinolin-2-ones: Preparation and Biological Activity. Molecules. 2009; 14(3):1145-1159.

Chicago/Turabian Style

Jampilek, Josef; Musiol, Robert; Pesko, Matus; Kralova, Katarina; Vejsova, Marcela; Carroll, James; Coffey, Aidan; Finster, Jacek; Tabak, Dominik; Niedbala, Halina; Kozik, Violetta; Polanski, Jaroslaw; Csollei, Jozef; Dohnal, Jiri. 2009. "Ring-substituted 4-Hydroxy-1H-quinolin-2-ones: Preparation and Biological Activity." Molecules 14, no. 3: 1145-1159.

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