Abstract
Ethanoanthracene cycloadducts (5-7) anti, (5-7) syn, and (5-7) dec have been synthesized from the Diels-Alder (DA) reaction of diene 1,8-dichloroanthracene 2, with the dienophiles; acrylonitrile 3, 1-cynavinyl acetate 4, and phenyl vinyl sulfone 5, individually. The steric effect of dienophile substituents were more favorable toward the anti-isomer formation as deduced from H-1-NMR spectrum. The cheminformatics prediction for (5-7) anti and (5-7) syn was investigated. The in silico anticipated anti-depression activity of the (5-7) anti and (5-7) syn compounds were investigated and compared to maprotiline 9 as reference anti-depressant drug. The study showed that steric interactions play a crucial role in the binding affinity of these compounds to the representative models; 4xnx, 2QJU, and 3GWU. The pharmacokinetic and drug-like properties of (5-7) anti and (5-7) syn exhibited that these compounds could be represented as potential candidates for further development into antidepressant-like agents.