Novel piperazine and morpholine substituted quinolines: Selective synthesis through activation of 3,6,8-tribromoquinoline, characterization and their some metabolic enzymes inhibition potentials

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dc.contributor.authorCakmak, Osman
dc.contributor.authorOkten, Salih
dc.contributor.authorAlimli, Dilek
dc.contributor.authorErsanli, Cem Cuneyt
dc.contributor.authorTaslimi, Parham
dc.contributor.authorKocyigit, Umit Muhammet
dc.date.accessioned2021-01-14T18:10:20Z
dc.date.available2021-01-14T18:10:20Z
dc.date.issued2020
dc.departmentKKÜ
dc.descriptionTaslimi, Parham/0000-0002-3171-0633; Okten, Salih/0000-0001-9656-1803
dc.description.abstractRegioselective routes are described for convenient preparation of novel piperazine/morpholine substituted quinoline derivatives at C-3, C-6 and C-8 starting with 3,6,8-tribromoquinoline (6) by nucleophilic substitution via conventional heating or microwave assisted reaction conditions. 3,6,8-Tribromoquinoline (6) was treated with piperazine and morpholine under microvawe irradiation, which selectively furnished 3-mopholinyl and 3-piperazinyl quinoline derivatives 7 and 8 in yields of 58% and 60%, respectively. On the other hand, the activation of benzene cycle of quinoline by nitration of 3,6,8-tribromoquinoline, giving 5-nitro-3,6,8-tribromoquinoline (18) in quantitative yield, was enabled. Then, the bromines at C-6 and C-8 were selectively exchanged by morpholine and piperazine via SNAr reactions. Thus, 6,8-dimopholinylquinoline (22) and 5-nitro-6,8-dipiperazinylquinoline (24), biologically valuable derivatives, were prepared in high yields (82% and 72%, respectively). The synthesized compounds were fully characterizated by H-1 NMR, C-13 NMR, 2D NMR, XRD, HRMS and IR spectra. The novel molecules had effective inhibition profiles against some metabolic enzymes. Also, they have the potential of drug candidates to treat of some diseases including glaucoma, epilepsy, Alzheimer's disease (AD), leukemia, and type-2 diabetes mellitus (T2DM). (C) 2020 Elsevier B.V. All rights reserved.en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [112T394]en_US
dc.description.sponsorshipThis study was financially supported by grants from the Scientific and Technological Research Council of Turkey (TUBITAK, Project number: 112T394). The authors thank to Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8-QUEST diffractometer.en_US
dc.identifier.citationclosedAccessen_US
dc.identifier.doi10.1016/j.molstruc.2020.128666
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85086755228
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2020.128666
dc.identifier.urihttps://hdl.handle.net/20.500.12587/12524
dc.identifier.volume1220en_US
dc.identifier.wosWOS:000573639200003
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherELSEVIERen_US
dc.relation.ispartofJOURNAL OF MOLECULAR STRUCTURE
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectNitrationen_US
dc.subjectQuinolineen_US
dc.subjectPiperazine substituted quinolineen_US
dc.subjectMorpholine substituted quinolineen_US
dc.subjectEnzyme inhibitionen_US
dc.titleNovel piperazine and morpholine substituted quinolines: Selective synthesis through activation of 3,6,8-tribromoquinoline, characterization and their some metabolic enzymes inhibition potentialsen_US
dc.typeArticle

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