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New thienobenzo/naphtho-triazoles as butyrylcholinesterase inhibitors. Design, synthesis and computational study

Mlakić, Milena; Selec, Ida; Ćaleta, Irena; Odak, Ilijana; Barić, Danijel; Ratković, Ana; Molčanov, Krešimir; Škorić, Irena (2023) New thienobenzo/naphtho-triazoles as butyrylcholinesterase inhibitors. Design, synthesis and computational study. International journal of molecular sciences, 24 (6). ISSN 1422-0067

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This study aims to test the inhibition potency of new thienobenzo/naphtho- triazoles toward cho- linesterases, evaluate their inhibition selectivity, and interpret the obtained results by molecular modeling. The synthesis of 19 new thienobenzo/naphtho-triazoles by two different approaches resulted in a large group of molecules with different functionalities in the structure. As predicted, most prepared molecules show better inhibition of the enzyme butyrylcholinesterase (BChE), con-sidering that the new molecules were designed according to the previous results. Interestingly, the binding affinity of BChE for even seven new compounds (1, 3, 4, 5, 6, 9, and 13) was similar to that reported for common cholinesterase inhibitors. According to computational study, the active thienobenzo- and naphtho-triazoles are accommodated by cholinesterases through H-bonds in-volving one of the triazole's nitrogens, pi-pi stacking between the aromatic moieties of the ligand and aromatic residues of the active sites of cholinesterases, as well as pi-alkyl interactions. For the future design of cholinesterase inhibitors and search for therapeutics for neurological disorders, compounds with a thienobenzo/naphtho-triazole skeleton should be considered.

Item Type: Article
Uncontrolled Keywords: cholinesterases ; photochemistry ; synthesis ; 1, 2, 3-triazoles ; inhibition
Subjects: NATURAL SCIENCES > Physics
Divisions: Division of Physical Chemistry
Depositing User: Danijela Barić
Date Deposited: 20 Jun 2023 13:38
DOI: 10.3390/ijms24065879

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