European Journal of Biomedical and Pharmaceutical Sciences

SYNTHESIS, CHARACTERIZATION AND EVALUATION OF ANTIMICROBIAL AND ANTIOXIDANT ACTIVITIES OF NEW SULFONAMIDE AND CARBAMATE DERIVATIVES OF 3-(TRIFLUOROMETHYL)-5,6,7,8-TETRA HYDRO-[1,2,4]-TRIAZOLO(4,3-?)-PYRAZINE (SITAGLIPTIN INTERMEDIATE)

Vadabingi Nagalakshmamma, Pulluru Hari Babua, Kollu Umapriya, Chamarthi Naga Raju, Allagadda Rajasekhar, Chippada Apparao and P. V. Chalapathi*

ABSTRACT

3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]-triazolo(4,3-α)-pyrazine (Sitagliptin intermediate) (1) is a potent pharmacophore in sitagliptin and the drug is a selective dipeptidile peptidase-4 (DPP-4) inhibitor used for the treatment of type-2 diabetes mellitus (T2DM). The synthesis of a series of new sulphonamide (7a-g) and carbamate derivatives (7h-j) was accomplished in high yields by reacting equimolar quantities of substituted sulfonyl chlorides and chloroformates with compound 1 using 1,4-dimethyl piperazine as a base at 40-50 oC. The structures of the synthesized compounds were confirmed by IR, NMR (1H,13C), mass spectra and elemental analysis. The title compounds were screened for their antimicrobial antioxidant activities (DPPH, H2O2 and NO methods) and IC50 values were also determined. The compounds 7a, 7c and 7f exhibited potent activity while the rest showed moderate activity against bacteria, fungi and also antioxidant activity.

Keywords: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]-triazolo(4,3-?)-pyrazine, (Sitagliptin Intermediate), Dipeptidile Peptidase-4, Diabetes Mellitus-2, Antimicrobial activity, Antioxidant activity.