Design and synthesis of tetrahydrochromeno[3,4-]isoindole-1,3(2,3a)-dione derivatives the Diels-Alder reaction: molecular docking, antibacterial activity, ADMET analysis and photophysical properties.

A series of fused tetrahydrochromeno[3,4-]isoindole-1,3(2,3a)-dione derivatives was successfully synthesized the Diels-Alder reaction. Molecular docking studies were conducted to understand the interaction modes between the synthesized hybrid compounds and the receptor bacterial strains of () and (). Notably, the results demonstrated that compound 19l (-8.7 kcal mol with and -8.4 kcal mol with ) and 19p (-8.7 kcal mol with and -9.1 kcal mol with ) exhibited good binding values. Additionally, the antibacterial studies showed that compounds 19l and 19p demonstrated excellent antibacterial activities, with a zone of inhibition (ZI) of 17 mm and a minimum inhibitory concentration (MIC) of 12.5 μg mL against both and , which were comparable to the performance of the standard antibiotic ciprofloxacin. Further, the bioavailability was assessed through virtual ADMET parameters, which suggested that most of the compounds possessed favorable pharmacokinetic profiles. To further enrich the study, photophysical properties of all the synthesized molecules were also examined using UV-visible and fluorescent spectroscopies.