Heterocyclic chemistry plays a crucial role in drug design and the development of novel biologically active compounds. Many synthetic products with diverse pharmacological benefits feature heterocyclic structures, making them essential in the medicinal field.

One notable class of heterocycles is 4-hydroxyquinolin-2-one, which hold significant importance in medicinal chemistry. 4-hydroxyquinolin-2-ones find wide-ranging applications as therapeutic agents, exhibiting antibacterial, anticancer, antiproliferative, analgesic, antiallergenic, and antitubercular activities. They have also been identified as antagonists of the cannabinoid type 2 receptor and modulators of glycogen synthase kinase GSK-3.

To continue our research into the synthesis of new bioactive agents; we synthesized and characterized a derivative of 4-hydroxyquinolin-2-one. This synthesis involved a two-step process: initially, we produced an enaminone by condensing cyclohexylamine with dimedone, employing ultrasonic irradiation and CuBr as a catalyst. Subsequently, in the second step, we reacted the prepared enaminone with diethylmalonate, utilizing microwave irradiation. Moreover, a molecular docking study was performed to explore the binding mode of studied compound within the active site of Eg5 enzyme. The results showed a good stability of the 4-hydroxyquinoilone inside the cavity with an interesting docking score. Additionally, we conducted an in-silico investigation to predict the drug-likeness and ADME (Absorption, Distribution, Metabolism, and Excretion) properties of the compound, utilizing MolSoft and SwissADME as precise predictive tools.