Design, synthesis, and assessment of pharmacological properties of indole-based fluorinated chalcones and their benzenesulfonamide analogs

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dc.authoridYamali, Cem/0000-0002-4833-7900
dc.authorscopusid55783407400
dc.authorscopusid57190746620
dc.authorscopusid56707307400
dc.authorscopusid57660492800
dc.authorscopusid57215669886
dc.authorscopusid56690319800
dc.authorscopusid17344644700
dc.contributor.authorYamalı, Cem
dc.contributor.authorSevin, Sedat
dc.contributor.authorNenni, Merve
dc.contributor.authorSakarya, Mehtap Tugrak
dc.contributor.authorUyar, Recep
dc.contributor.authorAygul, Abdurrahman
dc.contributor.authorUlger, Mahmut
dc.date.accessioned2024-08-25T18:38:32Z
dc.date.available2024-08-25T18:38:32Z
dc.date.issued2023
dc.departmentEge Üniversitesien_US
dc.description.abstractInfections, metabolic diseases, and cancer are the primary causes of death worldwide. The lack of efficacy, low selectivity, and emergence of resistance in clinically used medications require the search for new drug candidates. In this study, 3-(1H-indol-3-yl)-1-arylprop-2-en-1-ones and 2-(3-(3-oxo-3-arylprop-1-en-1-yl)-1H-indol-1-yl)-N-(4-sulfamoylphenyl)acetamides were designed and synthesized. Chemical structures of the compounds were elucidated by 1H NMR, 13C NMR, and HRMS. Antibacterial and antituberculosis effects of the compounds were investigated by REMA method. DPPH assay was used to test antioxidant effects. Cytotoxicity experiments were carried out by MTT assay. Chalcone-type compound 5 and sulfonamide derivative compound 9 draw attention with the lowest MIC = 15.62 & mu;g/ml values against M. tuberculosis. Compound 3 was the most potent antibacterial agent against A. baumannii and A. hydrophila, which cause severe infections in immunocompromised persons. Fluorinated chalcone derivatives 3, 4, 5 and sulfonamide derivative compound 8 were the most effective compounds in the series with the lowest MIC value of 62.5 & mu;g/ml against C. albicans. Compounds 6 (IC50 = 13.946 & mu;M) and 10 (IC50 = 18.844 & mu;M) showed antioxidant activity. The sulfonamide derivatives were moderate cytotoxic against Caco-2 cell line, while they had no considerable cytotoxicity against MCF-7 cell lines. The results showed that the most potent sulfonamide-based indole chalcones 9 and 10 were less toxic against non-cancer HUVEC cell compared to 5-FU with IC50 values 110.78 & PLUSMN; 49 & mu;g/ml and 83.44 & PLUSMN; 32 & mu;g/ml. Considering the prominent challenges of drug resistance and low bioavailability in antibacterial and anticancer therapies, the lead compounds investigated in this work possess potential for the development of innovative chemotherapeutic agents.en_US
dc.description.sponsorshipCukurova University BAP office [TSA-2021-13443]en_US
dc.description.sponsorshipThis study was funded by Cukurova University BAP office (Project ID: TSA-2021-13443). We would like to thank Ozden Tari for using the melting-point apparatus in Cukurova University Faculty of Pharmacy Student Laboratory.en_US
dc.identifier.doi10.1007/s11696-023-03060-3
dc.identifier.issn0366-6352
dc.identifier.issn2585-7290
dc.identifier.scopus2-s2.0-85171282389en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1007/s11696-023-03060-3
dc.identifier.urihttps://hdl.handle.net/11454/101060
dc.identifier.wosWOS:001066932000004en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherSpringer Int Publ Agen_US
dc.relation.ispartofChemical Papersen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.snmz20240825_Gen_US
dc.subjectIndoleen_US
dc.subjectChalconeen_US
dc.subjectSulfonamideen_US
dc.subjectAntimicrobialen_US
dc.subjectAntioxidanten_US
dc.subjectCytotoxicityen_US
dc.subjectCarbonic-Anhydrase Inhibitorsen_US
dc.subjectSulfonamide Hybridsen_US
dc.subjectCancer-Cellsen_US
dc.subjectHca Ixen_US
dc.subjectAnticanceren_US
dc.subjectBioactivitiesen_US
dc.subjectDerivativesen_US
dc.subjectDiscoveryen_US
dc.subjectApoptosisen_US
dc.subjectPathwaysen_US
dc.titleDesign, synthesis, and assessment of pharmacological properties of indole-based fluorinated chalcones and their benzenesulfonamide analogsen_US
dc.typeArticleen_US

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