The constant increase in the resistance of pathogenic bacteria to the commonly used drugs so far makes it necessary to search for new substances with antibacterial activity. Taking up this challenge, we obtained a series of rhodanine-3-carboxyalkyl acid derivatives containing 2- or 3- or 4-pyridinyl moiety at the C-5 position. These compounds were tested for their antibacterial and antifungal activities. They showed activity against Gram-positive bacteria while they were inactive against Gram-negative bacteria and yeast. In order to explain the relationship between the activity of the compounds and their structure, for selected derivatives crystal structures were determined using the X-ray diffraction method. Modeling of the isosurface of electron density was also performed. For all tested compounds their lipophilicity was determined by the RP-TLC method and by calculation methods. On the basis of the carried-out research, it was found that the derivatives with 1.5 N···S electrostatics interactions between the nitrogen atom in the pyridine moiety and the sulfur atom in the rhodanine system showed the highest biological activity.

Department of Analytical Chemistry and Biochemistry Faculty of Materials Science and Ceramics AGH University of Science and Technology Mickiewicza 30 30 059 Kraków Poland

Department of Chemistry University of Hradec Králové Rokitanského 62 500 03 Hradec Králové 3 Czech Republic

Department of Pharmaceutical Microbiology Medical University of Lublin Chodźki 1 20 093 Lublin Poland

Faculty of Chemistry Jagiellonian University in Kraków Gronostajowa 2 30 387 Kraków Poland

Faculty of Chemistry University of Lodz Tamka 12 91 403 Łódź Poland

Institute of Biology Pedagogical University of Krakow Podchorążych 2 30 084 Kraków Poland

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