Synthesis, characterization and biological evaluation of N-substituted triazinane-2-thiones and theoretical-experimental mechanism of condensation reaction

Abstract

The synthesis of triazinthions and their reactions with some nucleophilic reagents have been investigated during this scientific study. Thus, thiourea with a single component has been synthesized as a result of concomitant reactions of aldehyde and amines trials. The structure of the synthesized compounds was confirmed by H-1, C-13 NMR spectroscopy methods. The inhibitory effects of novel N-substituted triazinane-2-thione derivatives on acetylcholinesterase (AChE) activity were performed according to the spectrophotometric method of Ellman et al. These novel N-substituted triazinane-2-thiones derivatives were effective inhibitors of the alpha-glycosidase, cytosolic carbonic anhydrase I and II isoforms (hCA I and II), and Acetylcholinesterase (AChE) enzymes with K-i values in the range of 1.01 +/- 0.28 to 2.12 +/- 0.37 nm for alpha-glycosidase, 13.44 +/- 4.39 to 74.98 +/- 6.25 nm for hCA I, 10.41 +/- 4.8 to 72.6 +/- 17.66 nm for hCA II, 36.82 +/- 9.95 to 108.48 +/- 1.17 nm for AChE, and 624.62 +/- 100.34 to 1124.16 +/- 205.14 nm for alpha-glycosidase, respectively.