Synthesis and biological evaluation of fused dipyranoquinolinones as inhibitors of acetylcholinesterase with antioxidant properties

Abstract

Bis-fused pyridopyranocoumarins are prepared in excellent yields through the triple bond activation of propargylaminopropargyloxycoumarins or propargylamino (Kontogiorgis et al., 2012; Zhang et al., 2014) [7,8]-fused pyranocoumarins by gold nanoparticles supported on TiO2 under microwave irradiation. The intermediate new propargylaminopropargyloxycoumarins are synthesized through propargylation of 6-amino-7-hydroxycoumarins or 6-amino-4-hydroxycoumarin. Preliminary biological tests indicated remarkable antioxidant and anti-AChE activities of the new compounds and especially for 16a and 19b which present also druglikeness following the rule of five.

Keywords

• Au-nanoparticles
• Pyranocoumarins
• Pyridocoumarins
• Fused dipyranoquinolinones
• Propargyloxypropargylaminocoumarins
• Antioxidant activity