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

Cakmak, Osman; Okten, Salih; Alimli, Dilek; Ersanli, Cem Cuneyt; Taslimi, Parham; Kocyigit, Umit Muhammet


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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/89117</identifier>
  <creators>
    <creator>
      <creatorName>Cakmak, Osman</creatorName>
      <givenName>Osman</givenName>
      <familyName>Cakmak</familyName>
      <affiliation>Istanbul Rumeli Univ, Fac Arts &amp; Design, Dept Gastron, TR-34570 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Okten, Salih</creatorName>
      <givenName>Salih</givenName>
      <familyName>Okten</familyName>
      <affiliation>Kirikkale Univ, Fac Educ, Dept Math &amp; Sci Educ, Div Sci Educ, TR-71450 Yahsihan, Kirikkale, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Alimli, Dilek</creatorName>
      <givenName>Dilek</givenName>
      <familyName>Alimli</familyName>
      <affiliation>TUBITAK BILGEM, Semicond Technol Res Lab, TR-41400 Kocaeli, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Ersanli, Cem Cuneyt</creatorName>
      <givenName>Cem Cuneyt</givenName>
      <familyName>Ersanli</familyName>
      <affiliation>Sinop Univ, Fac Arts &amp; Sci, Dept Phys, TR-57010 Sinop, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Taslimi, Parham</creatorName>
      <givenName>Parham</givenName>
      <familyName>Taslimi</familyName>
      <affiliation>Bartin Univ, Fac Sci, Dept Biotechnol, TR-74100 Bartin, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Kocyigit, Umit Muhammet</creatorName>
      <givenName>Umit Muhammet</givenName>
      <familyName>Kocyigit</familyName>
      <affiliation>Cumhuriyet Univ, Fac Pharm, Dept Basic Pharm Sci, TR-58140 Sivas, Turkey</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Novel Piperazine And Morpholine Substituted Quinolines: Selective Synthesis Through Activation Of 3,6,8-Tribromoquinoline, Characterization And Their Some Metabolic Enzymes Inhibition Potentials</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2020</publicationYear>
  <dates>
    <date dateType="Issued">2020-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/89117</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1016/j.molstruc.2020.128666</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">Regioselective 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.</description>
  </descriptions>
</resource>
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