Synthesis and anticholinesterase activity of a novel series of acetazolamide condensed 1,4-dihydropyridines

Abstract

A novel Acetazolamide condensed 1, 4-dihydropyridines was set up by treating of N-(5-acetamido-1, 3, 4-thiadiazol-2-ylsulfonyl)-3-oxobutanamide with an aryl aldehyde and 25–30% alkali with sight amount of barium nitrate as a catalyst. Confirmation of the synthetic structure of the titled compounds (4–16) was substantiated by thin-layer chromatography (TLC), IR, 1H NMR, 13C NMR, Mass spectra (MS) and elemental analysis(C, H, and N) were finished. The titled compounds were assessed for anticholinesterase activity against acetylcholinesterase and butyl cholinesterase enzymes. The titled compound produced weak, moderate, or high anticholinesterase activity. Particularly, compound 8 demonstrated the best anticholinesterase activity of all the 1,4-dihydropyridines, with an IC50 estimation of 0.08 μM and 2.9 μM. Keywords: Acetazolamide, Anticholinesterase, 1,4-Dihydropyridines, Acetylcholinesterase, Butyl cholinesterase