Substituent effects in the formation of a few acenaphthenone-2-ylidene ketones and their molecular docking studies and in silico ADME profile

•Successfully studied the substituent effects in the reaction between 4-substituted acetophenones and acenaphthenequinone in the presence of KOH in methanol.•We have analysed the molecular docking studies of the synthesised acenaphthenone-2-ylidene ketones to selected proteins.•Studied the drug-likeness characters of acenaphthenone-2-ylidene ketones based on Lipinski's rules. We observed intriguing substituent effects in the reaction between 4-substituted acetophenones and acenaphthenequinone in the presence of KOH in methanol. In all cases, expected Claisen-Schimdt condensation was the first step. However, depending on the nature of 4-substituent on acetophenone, the initially formed condensation product remain unchanged or underwent Domino sequence of reactions to give three different 2:2 adducts arising through three distinct pathways. The interactions of acenaphthenone-2-ylidene ketones with the target proteins were performed by molecular docking studies. The prediction of in silico ADME belongings of the synthesized compounds revealed substantial drug-likeness characters based on Lipinski's rules.