Mlakic_2022_Bioorg.Chem_121_105701

New 1,2,3-triazolostilbenes were synthesized and photochemically transformed to substituted naphthotriazoles as electrocyclization products in high isolated yields for studying the acetyl- and butyrylcholinesterase inhibitory and anti-inflammatory activity. The best experimental results showed the naphthotriazole photoproducts providing interesting observation on cholinesterase inhibition associated with the inhibition of TNFalpha cytokine production. The geometries of synthesized triazolostilbenes were computationally examined using Density Functional Theory (DFT), followed by time-dependent DFT calculations to obtain insight into electronic properties observed by UV-Vis spectroscopy. The complexes between selected compounds with the active site of AChE are assessed by docking. A quantum mechanical cluster approach was utilized to optimize their structures, thus providing insight into the stabilizing interactions between the potential inhibitor and the active site.