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Structure-Lipophilicity Relationships in Series of Quinoline Derivatives

Robert Musiol 1Josef Jampilek 2Barbara Podeszwa 1Jacek Finster 1Dominik Tabak 1Jaroslaw Polanski 1

1. University of Silesia, Bankowa 12, Katowice 40-007, Poland
2. Zentiva AS, U Kabelovny 130, Prague 10237, Czech Republic


Quinoline derivatives have shown a wide range of biological activities [1]. Derivatives of the 8-hydroxyquinoline were studied as potential HIV-1 integrase inhibitors [2] and as potential antifungal agents [3, 4]. Their herbicidal effects were reported as well [3, 5].

One of the major prerequisites for pharmacological screening and drug development is the prediction of absorption, e.g. the transport of a molecule through cellular membranes. The drugs cross biological barriers most frequently through passive transport, which strongly depends on their lipophilicity. In general lipophilicity is one of the most important physical properties of biologically active compounds. This feature were assigned for combinatorial library of the ring-substituted quinoline derivatives by calculation using commercially available computer programs and by means of the RP-HPLC techniques for the lipophilicity measurement.


In the present study the correlation between RP-HPLC retention parameter log K (the logarithm of capacity factor K) and log P data calculated in various ways is discussed as well as the relationships between the lipophilicity and the chemical structure of the studied compounds.

The study was supported in part by a grant from KBN Warsaw: 4T09A 088 25.

[1] H. J. Roth, H. Fenner, in Arzneistoffe 3rd ed.; Deutscher Apotheker Verlag: Stuttgart, 2000; pp. 51-114.

[2] J. Polanski, H. Niedbala, R. Musiol, D. Tabak, B. Podeszwa, R. Gieleciak, A. Bak, A. Palka, T. Magdziarz, Acta Pol. Pharm. Drug Res. 2004, 61, 3.

[3] J. Jampilek, M. Dolezal, J. Kunes, V. Buchta, L. Silva, K. Kralova, Med. Chem. 2005, 1, 591.

[4] R. Musiol, J. Jampilek, V. Buchta, L. Silva, H. Niedbala, B. Podeszwa, A. Palka, K. Majerz-Maniecka, B. Oleksyn, J. Polanski, Bioorg. Med. Chem. 2006, 14, 3592.

[5] R. Musiol, J. Jampilek, K. Kralova, B. Podeszwa, J. Finster, H. Niedbala, A. Palka, J. Polanski, ECSOC-9 2005, November 1-30,


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Presentation: poster at 18th Conference on Physical Organic Chemistry, Posters, by Robert Musiol
See On-line Journal of 18th Conference on Physical Organic Chemistry

Submitted: 2006-04-21 14:22
Revised:   2009-06-07 00:44