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HETEROCYCLES 47. SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF SOME NEW THIAZOLE AURONES AS ANTIPROLIFERATIVE AGENTS

FANA-MARIA COMAN 1, ARMELLE T. MBAVENG 2,3, GABRIEL MARC 4, DENISA LEONTE 1, BALÁZS BRÉM 5, LAURIAN VLASE 6, SILVIA IMRE 7, VICTOR KUETE 2,3, VALENTIN ZAHARIA 1*

1.“Iuliu Haţieganu” University of Medicine and Pharmacy, Faculty of Pharmacy, Department of Organic Chemistry, 41 Victor Babeș Street, 400012, Cluj-Napoca, Romania
2 .“Johannes Gutenberg” University, Institute of Pharmacy and Biochemistry, Department of Pharmaceutical Biology, Stawdenger Weg 5, 55128, Mainz, Germany
3 .University of Dschang, Faculty of Science, Department of Biochemistry, Cameroon
4 .“Iuliu Haţieganu” University of Medicine and Pharmacy, Department of Pharmaceutical Chemistry, 8 Victor Babeș Street, 400012, Cluj-Napoca, Romania
5 .“Babeş-Bolyai” University, Faculty of Chemistry and Chemical Engineering, 11 Arany János Street, 400028, Cluj-Napoca, Romania
6 .“Iuliu Haţieganu” University of Medicine and Pharmacy, Department of Pharmaceutical Technology and Biopharmacy, 41 Victor Babeș Street, 400012, Cluj-Napoca, Romania
7 .University of Medicine, Pharmacy, Science and Technology of Târgu Mureș, Department of Analytical Chemistry and Drug Analysis, 38 Gheorghe Marinescu Street, 540139, Târgu Mureș, Romania

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New substituted thiazole aurones 2a-o were synthesized and evaluated for their anticancer activity. A screening of methods based on the oxidative cyclization of ortho-hydroxychalcones, with different agents, was applied in order to find the optimal way for the synthesis of these compounds. The best oxidizing agent proved to be mercury(II) acetate and it allowed the synthesis of the thiazole aurones with yields of 70 - 86%. All synthesized compounds were purified and characterized by ESI-MS, 1H NMR, 13C NMR and IR. The cytotoxicity of the thiazole aurones was determined in a panel of nine cancer cell lines using doxorubicin as control. Compounds 2a, 2i and 2e displayed the best cytotoxic activities. The interactions between aurones 2a-o and topoisomerases I and II were assessed by means of the molecular docking study and their target molecule is predicted to be topoisomerase I. The evaluation of the results revealed the importance of the thiazole ring for establishing a hydrogen bond with His367 and Arg364.