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Molecules 2015, 20(12), 22188-22201; doi:10.3390/molecules201219841

Study of the Relationships between the Structure, Lipophilicity and Biological Activity of Some Thiazolyl-carbonyl-thiosemicarbazides and Thiazolyl-azoles

1
National Research and Development Institute for Cryogenic and Isotopic Technologies, 4th Uzinei Street, Râmnicu Vâlcea 240050, Romania
2
3Nano-SAE Research Centre, Faculty of Physics, University of Bucharest, P. O. Box MG-38, Bucharest-Măgurele RO-077125, Romania
3
SC Biotech Corp SRL, 4th Uzinei Street, Office C52, 2 Râmnicu Vâlcea 40050, Romania
4
Department of Chemistry and Chemical Engineering, Babeş-Bolyai University, 1st Mihail Kogălniceanu Street, Cluj-Napoca RO-400084, Romania
5
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Iuliu Haţieganu University of Medicine and Pharmacy, 41 Victor Babeş Street, Cluj-Napoca RO-400012, Romania
6
Department of Pharmacognosy, Faculty of Pharmacy, Iuliu Haţieganu University of Medicine and Pharmacy, 12 Ion Creangă Street, Cluj-Napoca RO-400010, Romania
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 20 October 2015 / Revised: 20 November 2015 / Accepted: 3 December 2015 / Published: 11 December 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [3186 KB, uploaded 11 December 2015]   |  

Abstract

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. View Full-Text
Keywords: thiosemicarbazide; thiazolyl-azole; lipophilicity; PCA; anti-inflammatory; antioxidant thiosemicarbazide; thiazolyl-azole; lipophilicity; PCA; anti-inflammatory; antioxidant
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MDPI and ACS Style

Tamaian, R.; Moţ, A.; Silaghi-Dumitrescu, R.; Ionuţ, I.; Stana, A.; Oniga, O.; Nastasă, C.; Benedec, D.; Tiperciuc, B. Study of the Relationships between the Structure, Lipophilicity and Biological Activity of Some Thiazolyl-carbonyl-thiosemicarbazides and Thiazolyl-azoles. Molecules 2015, 20, 22188-22201.

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