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 Programı
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.
dc.description.sponsorshipResearch Fund of Istanbul University-Cerrahpasa [FDK-2017-24871, FYL-2018-30488, FBA-2019-30472, FBA-2019-32783]
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).
dc.identifier.doi10.17344/acsi.2021.7123
dc.identifier.endpage199
dc.identifier.issn1318-0207
dc.identifier.issn1580-3155
dc.identifier.issue1
dc.identifier.pmid35298002
dc.identifier.scopus2-s2.0-85127729199
dc.identifier.scopusqualityQ3
dc.identifier.startpage187
dc.identifier.urihttps://doi.org/10.17344/acsi.2021.7123
dc.identifier.urihttps://hdl.handle.net/11501/1371
dc.identifier.volume69
dc.identifier.wosWOS:000779953600018
dc.identifier.wosqualityQ4
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.institutionauthorYeşil, Emin Ahmet
dc.institutionauthorid0000-0001-8559-1951
dc.language.isoen
dc.publisherSlovensko Kemijsko Drustvo
dc.relation.ispartofActa Chimica Slovenica
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subject5-Nitro-1,4-Naphthoquinone
dc.subjectHeterocyclic Ring
dc.subjectCuprac Method
dc.subjectCatalase Inhibition Activity
dc.subjectGrowth
dc.titleSynthesis of new regioisomers of 5-Nitro-1,4-Naphthoquinone, evaluation of antioxidant and catalase inhibition activities
dc.typeArticle

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