Synthesis of phthalimide and naphthalimide derived Biginelli compounds and evaluation of their anti-inflammatory and anti-oxidant activities

Abstract

In the present work, synthesis of phthalimide and naphthalimide derived Biginelli compounds was performed. Allylation of phthalic & naphthalic anhydride, followed by ozonolysis resulted in the formation of N-phathalimido/naphpthalimido acetaldehyde (2 and 7). These aldehydes were subjected to Biginelli reaction using urea/thiourea and divergent β-keto esters in the presence of sulfated tin oxide (5 mol%) as catalyst in ethanol reflux to produce the corresponding dihydropyrimidinone compounds (5a-j and 8a-h). Additionally, both their antioxidant and anti-inflammatory functions were carried out. Compounds 5e, 5f, 5i, and 5j have shown potent to moderate potent activity for both antioxidant and anti-inflamamtory activities when compared to standard. Compounds 8c and 8g have shown potent antioxidant and anti-inflamamtory activities when compared to other compounds.