Oxidation of cyanobenzocycloheptatrienes: Synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives

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dc.contributor.authorGuney, Murat
dc.contributor.authorCoskun, Ahmet
dc.contributor.authorTopal, Fevzi
dc.contributor.authorDastan, Arif
dc.contributor.authorGulcin, Ilhami
dc.contributor.authorSupuran, Claudiu T.
dc.date.accessioned2024-02-23T14:02:22Z
dc.date.available2024-02-23T14:02:22Z
dc.date.issued2014
dc.departmentNEÜen_US
dc.description.abstractThe oxidation of some cyanocycloheptatrienes with CrO3 and pyridine was investigated and a few new nitrile functionalised benzotropone derivatives were obtained. Photooxygenation reaction of these products was also studied. The structures of the formed products were determined on the basis of NMR spectroscopy and the formation mechanism of unusual products was discussed. Human carbonic anhydrase isoenzymes I, and II (hCA I and hCA II) inhibition properties of nitrile functionalized new benzotropone derivatives were also studied. Both CA isozymes were inhibited in the low micromolar range by these nitrile functionalized benzotropone analogues. The newly synthesized benzotropone derivatives showed inhibition constants in the sub-micromolar range (2.51-4.06 mu M). The best hCA I inhibition was observed in 5H-benzocycloheptene-7-carbonitrile (K-1: 2.88 +/- 0.86 mu M). On the other hand, 5-oxo-5H-benzocycloheptatriene-7-carbonitrile showed the powerful inhibitory effect against hCA II (K-i: 2.51 +/- 0.34 mu M). (C) 2014 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipTUBITAK [104T401]; Ataturk Universityen_US
dc.description.sponsorshipThe authors are indebted to TUBITAK (Project number 104T401 and TUBITAK-BAYG National Postdoctoral Fellowship Program for A.C.), and Ataturk University for financial supports. We would also like thank to Prof. Dr. Cavit Kazaz, Res. Assistant Baris Anil, Dr. Murat Acar, Res. Assistant Ufuk Atmaca for NMR experiments, mass spectra and elemental analyses.en_US
dc.identifier.doi10.1016/j.bmc.2014.04.007
dc.identifier.endpage3543en_US
dc.identifier.issn0968-0896
dc.identifier.issn1464-3391
dc.identifier.issue13en_US
dc.identifier.pmid24856184en_US
dc.identifier.scopus2-s2.0-84901938556en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage3537en_US
dc.identifier.urihttps://doi.org/10.1016/j.bmc.2014.04.007
dc.identifier.urihttps://hdl.handle.net/20.500.12452/11674
dc.identifier.volume22en_US
dc.identifier.wosWOS:000337215900035en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofBioorganic & Medicinal Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectBenzocycloheptatrieneen_US
dc.subjectBenzotroponeen_US
dc.subjectOxidationen_US
dc.subjectRearrangementen_US
dc.subjectNitrile-Substituted Drugsen_US
dc.subjectCarbonic Anhydrase Inhibitionen_US
dc.titleOxidation of cyanobenzocycloheptatrienes: Synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivativesen_US
dc.typeArticleen_US

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