An operationally simple and high yielding procedure for the synthesis of spirooxindole and spiroacenaphthylene derivatives is described by the condensation reaction between isatin/ acenaphthenequinone derivatives, malono derivatives, and CH activated carbonyl compounds in the presence of a catalytic amount of 1,4-Diazabicyclo[2.2.2]octane (DABCO) in
ethanol or H2O/EtOH mixture under reflux conditions. This procedure has also been applied successfully for the synthesis of novel bis-benzo[b]pyran derivatives.The ability of synthesized compounds in inhibition of Sirtuin 2 were investigated both in-vitro and in-silico. Some of these compounds showed moderate level activity against Sirtuin 2.