Synthesis, moleculer modeling, and carbonic anhydrase inhibitor effects of novel 1-(1-benzyl-2-oxoindolin-3- ylidene)-4-(3-sulfamoylphenyl)thiosemicarbazides

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dc.authorid0000-0001-6703-9389
dc.authorid0000-0001-5625-0189
dc.authorid0000-0002-0536-4212
dc.authorid0000-0002-6916-122X
dc.contributor.authorApaydın, Çağla Begüm
dc.contributor.authorCinek, Tuğçe
dc.contributor.authorNadaroğlu, Hayrunnisa
dc.contributor.authorKaralı, Nilgün
dc.date.accessioned2026-11-13T11:23:22Z
dc.date.available2026-11-13T11:23:22Z
dc.date.issued2026
dc.departmentFakülteler, Eczacılık Fakültesi, Eczacılık Meslek Bilimleri Bölümü, Farmasötik Kimya Ana Bilim Dalı
dc.description.abstractIn this study, we describe the synthesis of new 1-(1-benzyl-2-oxoindolin-3-ylidene)-4-(3-sulfamoylphenyl)thiosemicarbazides and evaluate their inhibitory activity against hCAs (6a–l). The inhibitory effects of compounds 6a–l were examined in vitro against hCA I, II, IX, and XII isoforms. Acetazolamide (AAZ) was employed as the standard reference compound in this study. The compounds 6a–l inhibited the tumor-associated hCA IX and XII isoenzymes at nanomolar levels, and showed weak inhibitory effects on the off-target hCA I and II isoenzymes. Selectivity index (SI) values of compounds 6a–l were determined to be significantly high for hCA IX and XII over hCA I and II compared to AAZ. Compound 6k (R1 = Cl, R2 = 3-Cl) showed the strongest inhibitory effect (Ki = 25.23 nM) and high selectivity (SI = 225, 185) against hCA IX over hCA I and II. Compound 6f (R1 = CH3, R2 = 4-Cl) was found to have the highest inhibitory effect (Ki = 36.65 nM) and high selectivity (SI = 377 and 192, respectively) against hCA XII over hCA I and II. Molecular docking and dynamic simulation analyses were conducted to explore how compounds 6f and 6k interact with active sites of hCA XII and IX enzymes.
dc.identifier.citationApaydın, Ç. B., Cinek, T., Nadaroğlu, H., & Karalı, N. (2026). Synthesis, moleculer modeling, and carbonic anhydrase inhibitor effects of novel 1-(1-benzyl-2-oxoindolin-3- ylidene)-4-(3-sulfamoylphenyl)thiosemicarbazides. ChemMedChem, 21(19), pp. 1-14. https://doi.org/10.1002/cmdc.70467
dc.identifier.doi10.1002/cmdc.70467
dc.identifier.endpage14
dc.identifier.issn1860-7187
dc.identifier.issn1860-7179
dc.identifier.issue19
dc.identifier.pmidPMID: 42860880
dc.identifier.startpage1
dc.identifier.urihttps://doi.org/10.1002/cmdc.70467
dc.identifier.urihttps://hdl.handle.net/20.500.13055/1718
dc.identifier.volume21
dc.identifier.wosWOS:001899400600001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakPubMed
dc.indekslendigikaynak.otherSCI-E - Science Citation Index Expanded
dc.institutionauthorCinek, Tuğçe
dc.institutionauthorid0000-0001-5625-0189
dc.language.isoen
dc.publisherWiley
dc.relation.ispartofChemMedChem
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subject2-Oxoindoline
dc.subjectCarbonic Anhydrase
dc.subjectMolecular Docking
dc.subjectSulfonamide
dc.subjectThiosemicarbazide
dc.titleSynthesis, moleculer modeling, and carbonic anhydrase inhibitor effects of novel 1-(1-benzyl-2-oxoindolin-3- ylidene)-4-(3-sulfamoylphenyl)thiosemicarbazides
dc.typeArticle
dspace.entity.typePublication

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