Carboxylate- and Sulfonate-Containing Quinazolin-4(3H)-one Rings: Synthesis, Characterization, and Carbonic Anhydrase I–II and Acetylcholinesterase Inhibition Properties

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dc.contributor.authorTokalı, Feyzi Sinan
dc.contributor.authorAlım, Zuhal
dc.contributor.authorYırtıcı, Ümit
dc.date.accessioned2025-01-21T16:27:04Z
dc.date.available2025-01-21T16:27:04Z
dc.date.issued2023
dc.departmentKırıkkale Üniversitesi
dc.description.abstractQuinazolines are a group of bioactive heterocyclic compounds with a wide range of biological activities and have gained an important place in the design of active drugs with various targets due to their pharmacological properties. Carbonic anhydrase (CA) and acetylcholinesterase (AChE) inhibitors are very important pharmacologically. In this study, inhibition effects of newly synthesized quinazolin-4(3H)-one derivatives on human erythrocyte CA-I (hCA-I) and CA-II (hCA-II) isoenzyme and AChE activity were investigated. The structures of the novel compounds were characterized by fourier-transform infrared (FTIR), nuclear magnetic resonance (NMR), and high-resolution mass spectroscopy (HRMS). All molecules showed strong inhibitory effect in all three enzymes. 4-[(4-Oxo-2-(phenoxymethyl)quinazolin-3(4H)-ylimino)methyl]phenyl furan-2-carboxylate for hCA-I (IC50: 205 nM), 4-[(4-oxo-2-(phenoxymethyl)quinazolin-3(4H)-ylimino)methyl]phenyl isobutyrate for hCA-II (IC50: 209 nM), and 4-[(4-oxo-2-(phenoxymethyl)quinazolin-3(4H)-ylimino)methyl]phenyl propionate for AChE (IC50: 14.2 nM) were the molecules that showed the strongest inhibitory effect. Molecular docking studies were carried out to elucidate the possible interaction mechanism of the molecules in the active site of the enzymes. The affinity scores of the most active compounds for hCA-I, hCA-II, and AChE were determined as ?134.765, ?147.423, and ?175.354 MolDock Score, respectively. © 2023 Wiley-VCH GmbH.
dc.identifier.doi10.1002/slct.202204191
dc.identifier.issn2365-6549
dc.identifier.issue8
dc.identifier.scopus2-s2.0-85148626489
dc.identifier.scopusqualityQ3
dc.identifier.urihttps://doi.org/10.1002/slct.202204191
dc.identifier.urihttps://hdl.handle.net/20.500.12587/23248
dc.identifier.volume8
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherJohn Wiley and Sons Inc
dc.relation.ispartofChemistrySelect
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_20241229
dc.subjectAcetylcholinesterase; carbonic anhydrase; docking; inhibition; quinazolin-4(3H)-one; Schiff base
dc.titleCarboxylate- and Sulfonate-Containing Quinazolin-4(3H)-one Rings: Synthesis, Characterization, and Carbonic Anhydrase I–II and Acetylcholinesterase Inhibition Properties
dc.typeArticle

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