Synthesis, characterization and alpha glucosidase inhibition activity of new phthalimide derivatives

Abstract EN

Three of intermediate imide compounds were synthesized through reacting of phthalic anhydride with glycine(compound2a), and tetrachlorophthalic anhydride with glycine, (S)-2-[(tert-Butoxycarbonyl)amino]-3-aminopropionic acid(compounds2b,c) respectively in dry toluene with azeotropic removal of water using Dean- stark apparatus then carboxyl functional group activated by refluxing with thionyl chloride, the resulted acid chloride(compounds 3a-c) were reacted with different amine (5-flourouracil, 4-chloroaniline, 4-bromoaniline, 2-amino thiazole, and pyrrolidine)(compounds 4a-e) , the compounds (5a-j)consider as end productswhile the compounds (5k-o) required further reaction to deprotect aliphatic amine this was achieved by treating the compounds with trifloruro acetic acid (TFA) to remove tert-Butoxycarbonyl group (compounds 6a-e).

The alpha glucosidase inhibitory activity of some synthesized compounds(5a, 5f, 6a)was evalutedagainst alpha-glucosidase enzyme extracted from Saccharomyces bacteria, p-αnitrophenol glucopyranoside (pNPG) was used as substrate and thestandard was acarbose.

All these test compounds showsexcellent inhibitory activity according to IC50 values which is ranging from (4.61-7.32 M).