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Synthesis, characterisation, biological evaluation and in silico studies of sulphonamide Schiff bases

ArticleAçık Erişim

Özet

Sulphonamides are biologically important compounds with low toxicity, many bioactivities and cost-effectiveness. Eight sulphonamide derivatives were synthesised and characterised by FT-IR, 13C NMR, 1H NMR, LC-MS and elemental analysis. Their inhibitory effect on AChE, and carbonic anhydrase I and II enzyme activities was investigated. Their antioxidant activity was determined using different bioanalytical assays such as radical scavenging tests with ABTS•+, and DPPH•+ as well as metal-reducing abilities with CUPRAC, and FRAP assays. All compounds showed satisfactory enzyme inhibitory potency in nanomolar concentrations against AChE and CA isoforms with KI values ranging from 10.14 ± 0.03 to 100.58 ± 1.90 nM. Amine group containing derivatives showed high metal reduction activity and about 70% ABTS radical scavenging activity. Due to their antioxidant activity and AChE inhibition, these novel compounds may be considered as leads for investigations in neurodegenerative diseases. © 2020, © 2020 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.

Anahtar Kelimeler

Acetylcholinesterasecarbonic anhydrasemolecular dockingsulphonamidesynthesisAntioxidantsBenzothiazolesCarbonic Anhydrase InhibitorsCarbonic AnhydrasesCholinesterase InhibitorsDose-Response Relationship, DrugHumansMolecular StructureSchiff BasesStructure-Activity RelationshipSulfonamidesSulfonic Acids3 [(3 bromo 2 hydroxybenzyl)amino]benzenesulfonamide3 [(3 bromo 2 hydroxybenzylidene)amino]benzenesulfonamide3 [(3 chloro 2 hydroxybenzyl)amino]benzenesulfonamide3 [(3 chloro 2 hydroxybenzylidene)amino]benzenesulfonamide4 [(3 bromo 2 hydroxybenzyl)amino]benzenesulfonamide4 [(3 bromo 2 hydroxybenzylidene)amino]benzenesulfonamide4 [(3 chloro 2 hydroxybenzyl)amino]benzenesulfonamide4 [(3 chloro 2 hydroxybenzylidene)amino]benzenesulfonamideacetazolamideamineantioxidantcarbonate dehydratase Icarbonate dehydratase II
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AlanDeğerDil
dc.contributor.authorDurgun, Mustafa
dc.contributor.authorTürkeş, Cüneyt
dc.contributor.authorIşık, Mesut
dc.contributor.authorDemir, Yeliz
dc.contributor.authorSaklı, Ali
dc.contributor.authorKuru, Ali
dc.contributor.authorGüzel, Abdussamat
dc.contributor.authorBeydemir, Şükrü
dc.contributor.authorAkocak, Suleyman
dc.contributor.authorOsman, Sameh M.
dc.contributor.authorAlOthman, Zeid
dc.contributor.authorSupuran, Claudiu T.
dc.date.accessioned2026-10-18T20:28:42.202812192Z
dc.date.available2026-10-18T20:28:42.202812192Z
dc.date.issued2020
dc.description.abstractSulphonamides are biologically important compounds with low toxicity, many bioactivities and cost-effectiveness. Eight sulphonamide derivatives were synthesised and characterised by FT-IR, 13C NMR, 1H NMR, LC-MS and elemental analysis. Their inhibitory effect on AChE, and carbonic anhydrase I and II enzyme activities was investigated. Their antioxidant activity was determined using different bioanalytical assays such as radical scavenging tests with ABTS•+, and DPPH•+ as well as metal-reducing abilities with CUPRAC, and FRAP assays. All compounds showed satisfactory enzyme inhibitory potency in nanomolar concentrations against AChE and CA isoforms with KI values ranging from 10.14 ± 0.03 to 100.58 ± 1.90 nM. Amine group containing derivatives showed high metal reduction activity and about 70% ABTS radical scavenging activity. Due to their antioxidant activity and AChE inhibition, these novel compounds may be considered as leads for investigations in neurodegenerative diseases. © 2020, © 2020 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.
dc.description.sponsorshipFunding text 1: This work was in part also funded by the Researchers Supporting Project No. (RSP-2019/1) King Saud University, Riyadh, Saudi Arabia. The authors thank Harran University, Scientific Research Council (HÜBAK, Projects number: 18168) for financial support.; Funding text 2: The authors thank Harran University, Scientific Research Council (HÜBAK, Projects number: 18168) for financial support.
dc.identifier.doi10.1080/14756366.2020.1746784
dc.identifier.endpage962
dc.identifier.issn1475-6366
dc.identifier.issue1
dc.identifier.pmcidPMC7170330
dc.identifier.pmid32249705
dc.identifier.scopus2-s2.0-85083022713
dc.identifier.startpage950
dc.identifier.urihttps://rdlopen.rawdatalibrary.net/r/ebyu/13901
dc.identifier.volume35
dc.language.isoen
dc.publisherTaylor and Francis Ltd
dc.relation.ispartofJournal of Enzyme Inhibition and Medicinal Chemistry
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectAcetylcholinesterase
dc.subjectcarbonic anhydrase
dc.subjectmolecular docking
dc.subjectsulphonamide
dc.subjectsynthesis
dc.subjectAntioxidants
dc.subjectBenzothiazoles
dc.subjectCarbonic Anhydrase Inhibitors
dc.subjectCarbonic Anhydrases
dc.subjectCholinesterase Inhibitors
dc.subjectDose-Response Relationship, Drug
dc.subjectHumans
dc.subjectMolecular Structure
dc.subjectSchiff Bases
dc.subjectStructure-Activity Relationship
dc.subjectSulfonamides
dc.subjectSulfonic Acids
dc.subject3 [(3 bromo 2 hydroxybenzyl)amino]benzenesulfonamide
dc.subject3 [(3 bromo 2 hydroxybenzylidene)amino]benzenesulfonamide
dc.subject3 [(3 chloro 2 hydroxybenzyl)amino]benzenesulfonamide
dc.subject3 [(3 chloro 2 hydroxybenzylidene)amino]benzenesulfonamide
dc.subject4 [(3 bromo 2 hydroxybenzyl)amino]benzenesulfonamide
dc.subject4 [(3 bromo 2 hydroxybenzylidene)amino]benzenesulfonamide
dc.subject4 [(3 chloro 2 hydroxybenzyl)amino]benzenesulfonamide
dc.subject4 [(3 chloro 2 hydroxybenzylidene)amino]benzenesulfonamide
dc.subjectacetazolamide
dc.subjectamine
dc.subjectantioxidant
dc.subjectcarbonate dehydratase I
dc.subjectcarbonate dehydratase II
dc.titleSynthesis, characterisation, biological evaluation and in silico studies of sulphonamide Schiff bases
dc.typeArticle
dspace.entity.typePublication
rdl.citation.scopus103
rdl.departmentDepartment of Biochemistry, Faculty of Pharmacy, Erzincan Binali Yıldırım University, Erzincan, Turkey.
rdl.oa.statusgold
rdl.source.indexSCOPUS
rdl.source.indexPUBMED