Synthesis, crystal structure, and biological evaluation of optically active 2?amino?4?aryl?7,7?dimethyl?5?oxo?5,6,7,8?tetrahydro?4H?chromen?3?carbonitriles: Antiepileptic, antidiabetic, and anticholinergics potentials

Abstract

In the presence of chiral organic catalysts, the optically active 4H-chromine was synthesized from the multicomponent condensation of 5,5-dimethylcyclohexane-1,3-dione with malononitrile and methylene-active compound, and the specific angle of rotation of the compounds was determined in the AUTOPOL-III polarimeter and their structures were confirmed by the X-ray spectroscopic analysis method. These optically active 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromen-3-carbonitriles were effective inhibitors of alpha-glycosidase, the cytosolic carbonic anhydrase I and II isoforms (hCA I and II), and acetylcholinesterase (AChE) enzymes with K-i values in the range of 21.33 +/- 1.11 to 40.24 +/- 10.78 mu M for hCA I, 28.91 +/- 6.51 to 59.97 +/- 15.62 mu M for hCA II, 18.16 +/- 3.18 to 66.57 +/- 1.36 mu M for alpha-glycosidase, and 8.68 +/- 0.93 to 102.61 +/- 24.96 mu M for AChE.