Study of the Relationships between the Structure, Lipophilicity and Biological Activity of Some Thiazolyl-carbonyl-thiosemicarbazides and Thiazolyl-azoles
Radu Tamaian,
Augustin Moţ,
Radu Silaghi-Dumitrescu,
Ioana Ionuţ,
Anca Stana,
Ovidiu Oniga,
Cristina Nastasă,
Daniela Benedec,
Brînduşa Tiperciuc
Affiliations
Radu Tamaian
National Research and Development Institute for Cryogenic and Isotopic Technologies, 4th Uzinei Street, Râmnicu Vâlcea 240050, Romania
Augustin Moţ
Department of Chemistry and Chemical Engineering, Babeş-Bolyai University, 1st Mihail Kogălniceanu Street, Cluj-Napoca RO-400084, Romania
Radu Silaghi-Dumitrescu
Department of Chemistry and Chemical Engineering, Babeş-Bolyai University, 1st Mihail Kogălniceanu Street, Cluj-Napoca RO-400084, Romania
Ioana Ionuţ
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Iuliu Haţieganu University of Medicine and Pharmacy, 41 Victor Babeş Street, Cluj-Napoca RO-400012, Romania
Anca Stana
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Iuliu Haţieganu University of Medicine and Pharmacy, 41 Victor Babeş Street, Cluj-Napoca RO-400012, Romania
Ovidiu Oniga
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Iuliu Haţieganu University of Medicine and Pharmacy, 41 Victor Babeş Street, Cluj-Napoca RO-400012, Romania
Cristina Nastasă
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Iuliu Haţieganu University of Medicine and Pharmacy, 41 Victor Babeş Street, Cluj-Napoca RO-400012, Romania
Daniela Benedec
Department of Pharmacognosy, Faculty of Pharmacy, Iuliu Haţieganu University of Medicine and Pharmacy, 12 Ion Creangă Street, Cluj-Napoca RO-400010, Romania
Brînduşa Tiperciuc
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Iuliu Haţieganu University of Medicine and Pharmacy, 41 Victor Babeş Street, Cluj-Napoca RO-400012, Romania
Lipophilicity, as one of the most important physicochemical parameters of bioactive molecules, was investigated for twenty-two thiazolyl-carbonyl-thiosemicarbazides and thiazolyl-azoles. The determination was carried out by reversed-phase thin-layer chromatography, using a binary isopropanol-water mobile phase. Chromatographically obtained lipophilicity parameters were correlated with calculated log P and log D and with some biological parameters, determined in order to evaluate the anti-inflammatory and antioxidant potential of the investigated compounds, by using principal component analysis (PCA). The PCA grouped the compounds based on the nature of their substituents (X, R and Y), indicating that their nature, electronic effects and molar volumes influence the lipophilicity parameters and their anti-inflammatory and antioxidant effects. Also, the results of the PCA analysis applied on all the experimental and computed parameters show that the best anti-inflammatory and antioxidant compounds were correlated with medium values of the lipophilicity parameters. On the other hand, the knowledge of the grouping patterns of the tested variables allows the reduction of the number of parameters, determined in order to establish the biological activity.
