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Synthesis, biological evaluation, and in silico study of novel library sulfonates containing quinazolin-4(3H)-one derivatives as potential aldose reductase inhibitorsTokalı, Feyzi SinanDemir, YelizDemircioğlu, İbrahim HakkıTürkeş, CüneytKalay, ErbayŞendil, KıvılcımBeydemir, ŞükrüADME-Toxaldose reductaseepalrestatin silico studymolecular dockingquinazolinones3 amino 2 ethylquinazolin 4(3h) one3 amino 2 isopropylquinazolin 4(3h) one4 formylphenyl 4 bromobenzenesulfonate4 formylphenyl 4 chlorobenzenesulfonate4 formylphenyl 4 fluorobenzenesulfonate4 formylphenyl 4 methoxybenzenesulfonate4 formylphenyl 4 methylbenzenesulfonate4 formylphenyl 4 nitrobenzenesulfonate4 formylphenyl benzenesulfonate4 [(2 isopropyl 4 oxoquinazolin 3[4h] ylimino)methyl]phenyl 4 methoxybenzenesulfonate4 [(2 isopropyl 4 oxoquinazolin 3[4h] ylimino)methyl]phenyl 4 methylbenzenesulfonate4 [(2 isopropyl 4 oxoquinazolin 3[4h] ylimino)methyl]phenyl benzenesulfonate4 [(2 isopropyl 4 oxoquinazolin 3[4h]ylimino)methyl]phenyl 4 bromobenzenesulfonate4 [(2 isopropyl 4 oxoquinazolin 3[4h]ylimino)methyl]phenyl 4 chlorobenzenesulfonate4 [(2 isopropyl 4 oxoquinazolin 3[4h]ylimino)methyl]phenyl 4 fluorobenzenesulfonate4 [(2 isopropyl 4 oxoquinazolin 3[4h]ylimino)methyl]phenyl 4 nitrobenzenesulfonate4 [(2 methyl 4 oxoquinazolin 3[4h] ylimino) methyl]phenyl 4 bromobenzenesulfonat4 [(2 methyl 4 oxoquinazolin 3[4h] ylimino) methyl]phenyl 4 chlorobenzenesulfona4 [(2 methyl 4 oxoquinazolin 3[4h] ylimino) methyl]phenyl 4 fluorobenzenesulfona4 [(2 methyl 4 oxoquinazolin 3[4h] ylimino) methyl]phenyl 4 methoxybenzenesulfonate4 [(2 methyl 4 oxoquinazolin 3[4h] ylimino) methyl]phenyl 4 methylbenzenesulfona4 [(2 methyl 4 oxoquinazolin 3[4h] ylimino) methyl]phenyl 4 nitrobenzenesulfonate4 [(2 methyl 4 oxoquinazolin 3[4h] ylimino) methyl]phenyl benzenesulfonate4(3h) quinazolinone derivativeA series of novel sulfonates containing quinazolin-4(3H)-one ring derivatives was designed to inhibit aldose reductase (ALR2, EC 1.1.1.21). Novel quinazolinone derivatives (1–21) were synthesized from the reaction of sulfonated aldehydes with 3-amino-2-alkylquinazolin-4(3H)-ones in glacial acetic acid with good yields (85%–94%). The structures of the novel molecules were characterized using IR, 1H-NMR, 13C-NMR, and HRMS. All the novel quinazolinones (1–21) demonstrated nanomolar levels of inhibitory activity against ALR2 (KIs are in the range of 101.50–2066.00 nM). Besides, 4-[(2-isopropyl-4-oxoquinazolin-3[4H]-ylimino)methyl]phenyl benzenesulfonate (15) showed higher inhibitor activity inhibited ALR2 up to 7.7-fold compared to epalrestat, a standard inhibitor. Binding interactions between ALR2 and quinazolinones have been investigated using Schrödinger Small-Molecule Drug Discovery Suite 2021–1, reported possible inhibitor-ALR2 interactions. Both in vitro and in silico study results suggest that these quinazolin-4(3H)-one ring derivatives (1–21) require further molecular modification to improve their drug nominee potency as an ALR2 inhibitor. © 2021 Wiley Periodicals, LLC.John Wiley and Sons Inc2022Articlehttps://rdlopen.rawdatalibrary.net/r/ebyu/12777https://doi.org/10.1002/ddr.218870272-4391enDrug Development Researchinfo:eu-repo/semantics/openAccessinfo:eu-repo/semantics/articlehttps://ebyu-rdlopen.rawdatalibrary.net/tr/items/ebyu/12777