Synthesis, Characterization and Alpha Glucosidase Inhibition Activity of New Phthalimide Derivatives

H. Ismeal, Sajida; H. Mohammed, Mohammed; A. M. Jawed, Hassan

	Synthesis, Characterization and Alpha Glucosidase Inhibition Activity of New Phthalimide Derivatives
Iraqi Journal of Pharmaceutical Sciences
Article 1, Volume 27, Issue 1, 2018, Pages 100-108
Authors
Sajida H. Ismeal; Mohammed H. Mohammed; Hassan A. M. Jawed
Abstract
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).
Keywords
Antidiabetic; synthesis; Phthalimide

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