Synthesis, Characterization and Alpha Glucosidase Inhibition activity of new Phthalimide Derivatives

  • Hassan ALi college of pharmacy al-mustansiryia university
  • Mohammed H. Mohammed
  • Sajida H. Ismeal

Abstract

 Three of imide intermediate products  were synthesized by reacting of phthalic anhydride with glycine (2a), and tetrachloro phthalic anhydride with glycine , (S)-2-[(tert-Butoxycarbonyl)amino]-3-aminopropionic acid ( 2b,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 (3a-c) were reacted with different amine (5-flourouracil, 4-chloroaniline, 4-bromoaniline, 2-amino thiazole, and pyrrolidine) (4a-e) , the   resulted products consider as the end products (5a-j) while  the compounds (5k-o) required further reaction to deprotect aliphatic amine this achieved by treating the compounds with TFA to remove tert-Butoxycarbonyl group (6a-e).


The alpha glucosidase inhibitory activity of some synthesized compounds (5a, 5f, 6a) were tested by using  -glucosidase from Saccharomyces cerevisiae, p-nitrophenol glucopyranoside (pNPG)  used as substrate and acarbose used as standard.


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

Published
Jun 5, 2018
How to Cite
ALI, Hassan; H. MOHAMMED, Mohammed; H. ISMEAL, Sajida. Synthesis, Characterization and Alpha Glucosidase Inhibition activity of new Phthalimide Derivatives. Iraqi Journal of Pharmaceutical Sciences ( P-ISSN: 1683 - 3597 , E-ISSN : 2521 - 3512), [S.l.], v. 27, n. 1, p. 100-108, june 2018. ISSN 1683-3597. Available at: <http://www.bijps.com/index.php/bijps/article/view/731>. Date accessed: 15 aug. 2018. doi: http://dx.doi.org/10.31351/vol27iss1pp100-108.