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.authoridTaslimi, Parham/0000-0002-3171-0633
dc.authoridERSANLI, CEM CUNEYT/0000-0002-8113-5091
dc.authoridOkten, Salih/0000-0001-9656-1803
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.accessioned2025-03-23T19:39:25Z
dc.date.available2025-03-23T19:39:25Z
dc.date.issued2020
dc.departmentSinop Üniversitesi
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.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [112T394]
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.
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/11486/6353
dc.identifier.volume1220
dc.identifier.wosWOS:000573639200003
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectNitration
dc.subjectQuinoline
dc.subjectPiperazine substituted quinoline
dc.subjectMorpholine substituted quinoline
dc.subjectEnzyme inhibition
dc.titleNovel piperazine and morpholine substituted quinolines: Selective synthesis through activation of 3,6,8-tribromoquinoline, characterization and their some metabolic enzymes inhibition potentials
dc.typeArticle

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