Romanian Society of Pharmaceutical Sciences
 

« Back to Farmacia Journal 4/2018

HETEROCYCLES 43. SYNTHESIS, CHARACTERIZATION AND ANTIOXIDANT ACTIVITY OF SOME THIAZOLE HYDROXYCHALCONES AND THEIR FLAVONOIDIC DERIVATIVES

TEODORA CONSTANTINESCU 1, DENISA LEONTE 1, LÁSZLÓ CSABA BENCZE 2, LAURIAN VLASE 3, SILVIA IMRE 4, DANIELA HANGANU 5, VALENTIN ZAHARIA 1*

1.”Iuliu Hațieganu” University of Medicine and Pharmacy, Department of Organic Chemistry, 41 Victor Babeș Street, Ro-400012 Cluj-Napoca, Romania
2.“Babeș-Bolyai” University, Faculty of Chemistry and Chemical Engineering, Biocatalysis and Biotransformation Research Group, 11 Arany János Street, Ro-400028 Cluj-Napoca, Romania
3.“Iuliu Hațieganu” University of Medicine and Pharmacy, Department of Pharmaceutical Technology and Biopharmacy, 41 Victor Babeș Street, Ro-400012 Cluj-Napoca, Romania
4.University of Medicine and Pharmacy, Department of Analytical Chemistry and Drug Analysis, 38 Gheorghe Marinescu Street, Ro-540139 Târgu Mureș, Romania
5.“Iuliu Hațieganu” University of Medicine and Pharmacy, Department of Pharmacognosy, 12 Ion Creangă Street, Ro-400010 Cluj-Napoca, Romania

Download Full Article PDF

Natural and synthetic chalcones are biologically active molecules, as well as precursors for the preparation of several pharmacologically useful compounds, belonging to the class of the epoxides, flavanones, flavones and aurones. The thiazole ring is present in the structure of many compounds with therapeutic potential. Starting from these premises, the aim of this study was the synthesis and characterization of new thiazole chalcones, flavanones and flavones and the evaluation of their antioxidant potential. Chalcones were obtained by applying the Claisen-Schmidt condensation of thiazole aldehydes with acetophenones substituted in ortho or para with a hydroxyl group. The ortho hydroxychalcones were used as precursors for the synthesis of thiazole flavanones and flavones, in different reaction conditions: flavanones were obtained by cyclization in acidic/basic catalysis and flavones were obtained by oxidative cyclization with iodine in dimethylsulfoxide (DMSO). The structures were confirmed by 1H NMR, 13C NMR, IR and MS analysis. The antioxidant activity was determined by 2,2-di-phenyl-1-picrylhydrazyl (DPPH) free radical scavenging method. The synthesized compounds have a low antioxidant activity.