Synthesis of new regioisomers of 5-Nitro-1,4-Naphthoquinone, evaluation of antioxidant and catalase inhibition activities

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dc.contributor.authorAbdassalam, Aesha Fsh
dc.contributor.authorDeniz, Nahide Gülşah
dc.contributor.authorSayil, Çiğdem
dc.contributor.authorÖzyürek, Mustafa
dc.contributor.authorYeşil, Emin Ahmet
dc.contributor.authorSalihoğlu, Hüseyin
dc.date.accessioned2024-06-13T20:18:27Z
dc.date.available2024-06-13T20:18:27Z
dc.date.issued2022
dc.departmentMeslek Yüksekokulu, Gedik Meslek Yüksekokulu, Kimya Teknolojisi Programıen_US
dc.description.abstractThe studies on nitronaphthoquinone derivatives are rare in the literature, and the nitro group associated with the aromatic ring in the quinone system is known to increase the biological activity of naphthoquinone due to its electron-withdrawing properties. In the course of quinone derivatives, the new N(H)-substituted-5-nitro-1,4-naphthoquinones (NQ) as regioisomers were synthesized by reactions of 2,3-dichloro-5-nitro-1,4-naphthoquinone with some heterocyclic ring substituted nucleophiles such as anilines, piperazines, or morpholines, according to a Michael 1,4-addition mechanism. Five NQ regioisomer couples having different functional group (2-chloro-isomers 3, 5, 7, 9 and 13; 3-chloro-isomers 2, 4, 6, 8 and 12) are reported here. All new synthesized compounds were characterized by spectroscopic methods and two-dimensional NMR techniques H-1-H-1 correlated spectroscopy (COSY). The synthesized NQ regioisomers were evaluated for catalase enzyme inhibitory activities and antioxidant efficiency. The synthesized regioisomers were screened for their antioxidant capacity using the cupric-reducing antioxidant capacity (CUPRAC) method. 2-Chloro-3-((2,4-dimethoxyphenyl)amino)-5-nitronaphthalene-1,4-dione (5) showed the highest antioxidant capacity with a 1.80 +/- 0.06 CUPRAC-trolox equivalent antioxidant capacity (TEAC) coefficient. Compound 5 also showed strongest catalase enzyme inhibitory activity. The antioxidant capacity results of all 2-chloro regioisomers are higher than the 3-chloro regioisomers. Likewise, also catalase enzyme inhibitory activities results were determined in the same way, except for one regioisomer pair. The catalase was effectively inhibited by the newly synthesized compounds, with % inhibition values in the range of 0.71-0.86%. Some of these NQ compounds also showed remarkable antioxidant capacities.en_US
dc.description.sponsorshipResearch Fund of Istanbul University-Cerrahpasa [FDK-2017-24871, FYL-2018-30488, FBA-2019-30472, FBA-2019-32783]en_US
dc.description.sponsorshipWe gratefully thank the Research Fund of Istanbul University-Cerrahpasa for financial support of this work (Project Numbers: FDK-2017-24871, FYL-2018-30488, FBA-2019-30472, FBA-2019-32783).en_US
dc.identifier.doi10.17344/acsi.2021.7123
dc.identifier.endpage199en_US
dc.identifier.issn1318-0207
dc.identifier.issn1580-3155
dc.identifier.issue1en_US
dc.identifier.pmid35298002en_US
dc.identifier.scopus2-s2.0-85127729199en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage187en_US
dc.identifier.urihttps://doi.org/10.17344/acsi.2021.7123
dc.identifier.urihttps://hdl.handle.net/11501/1371
dc.identifier.volume69en_US
dc.identifier.wosWOS:000779953600018en_US
dc.identifier.wosqualityQ4en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.institutionauthorYeşil, Emin Ahmet
dc.institutionauthorid0000-0001-8559-1951en_US
dc.language.isoenen_US
dc.publisherSlovensko Kemijsko Drustvoen_US
dc.relation.ispartofActa Chimica Slovenicaen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subject5-Nitro-1,4-Naphthoquinoneen_US
dc.subjectHeterocyclic Ringen_US
dc.subjectCuprac Methoden_US
dc.subjectCatalase Inhibition Activityen_US
dc.subjectGrowthen_US
dc.titleSynthesis of new regioisomers of 5-Nitro-1,4-Naphthoquinone, evaluation of antioxidant and catalase inhibition activitiesen_US
dc.typeArticleen_US

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