Synthesis of N-heterocyclic group containing triazole sulfonamide compounds

Triazol compounds are considered multifunctional heterocyclic compounds because they possess important pharmacological activities such as antifungal and antiviral activities, and fluconazole, itraconazole, ravuconazole, voriconazole and posaconazole are commercially available. Sulphonamides (sulpho drugs) are the first drugs that are widely and systematically used as chemotherapeutic agents against various diseases. The discovery of antibacterial and enzyme activity properties of sulfonamides have been a focus of scientific work. It is a known fact that enzymes have an effect on the malfunctioning of the human anotomy. The way to eliminate these malfunctions may be by increasing, decreasing the activity or to eliminate of the enzymes that cause it. The way to control these enzymes is through with functional groups of chemical compounds that can bind to metal groups in enzymes. Taking this into consideration, new derivatives thereof were synthesized by the reaction of sulfonamide, thionyl and alkyls which effects have been revealed in previous studies. In this study, N-propargylheterocyclic compounds were obtained by alkylation of N-heterocyclic compounds with propargyl bromide in DMF in basic medium. The azido sulphonamide was prepared by reacting the prepared sulfonylamide diazonium salt and sodium azide. The target compounds were synthesized by the 1,3-dipolar addition of the azidosulfonylamide compound to the N-propargylheterocyclic compounds. Structures of the synthesized final products were verified by elemental analysis, 1H NMR, 13C NMR, IR spectrometers. New 11 N-Heteroaryl bearing triazolosulfonamide compounds (6a-k) were synthesized and their inhibitory effects on the activity of purified human carbonic anhydrase I and II were evaluated. The results showed that all the synthesized compounds inhibited the CA isoenzyme activity. Among them, 6a was found to be the most active (IC50: 0.52 µM) for hCA-I and 6a (IC50: 0.34 µM) for hCA-II. Keywords: Sulfonamide, Heterocyclic, Sulfonamide, CA