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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. 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