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Acquiring stereospecific new pseudosugars: Obtaining<i> rac</i>-decahydro-1,4-epoxynaphthalene-2,3,5,6,7,8-hexaols from the Diels-Alder reaction and investigating their biological effects

Aydin, Gokay; Coban, Canan cakir; Kurbanoglu, N. Izzet; Turk, Mustafa; Baran, Arif


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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/282971</identifier>
  <creators>
    <creator>
      <creatorName>Aydin, Gokay</creatorName>
      <givenName>Gokay</givenName>
      <familyName>Aydin</familyName>
      <affiliation>Karamanoglu Mehmetbey Univ, Vocat Sch Healty Serv, TR-70200 Karaman, Turkiye</affiliation>
    </creator>
    <creator>
      <creatorName>Coban, Canan cakir</creatorName>
      <givenName>Canan cakir</givenName>
      <familyName>Coban</familyName>
      <affiliation>Karadeniz Tech Univ, Acad Data Management Syst, TR-61080 Trabzon, Turkiye</affiliation>
    </creator>
    <creator>
      <creatorName>Kurbanoglu, N. Izzet</creatorName>
      <givenName>N. Izzet</givenName>
      <familyName>Kurbanoglu</familyName>
      <affiliation>Sakarya Univ, Fac Educ, Dept Math &amp; Sci Educ, TR-54050 Sakarya, Turkiye</affiliation>
    </creator>
    <creator>
      <creatorName>Turk, Mustafa</creatorName>
      <givenName>Mustafa</givenName>
      <familyName>Turk</familyName>
      <affiliation>Kirikkale Univ, Fac Engn &amp; Architecture, Bioengn Dept, TR-71451 Kirikkale, Turkiye</affiliation>
    </creator>
    <creator>
      <creatorName>Baran, Arif</creatorName>
      <givenName>Arif</givenName>
      <familyName>Baran</familyName>
      <affiliation>Sakarya Univ, Fac Arts &amp; Sci, Chem Dept, TR-54050 Sakarya, Turkiye</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Acquiring Stereospecific New Pseudosugars: Obtaining&lt;I&gt; Rac&lt;/I&gt;-Decahydro-1,4-Epoxynaphthalene-2,3,5,6,7,8-Hexaols From The Diels-Alder Reaction And Investigating Their Biological Effects</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2025</publicationYear>
  <dates>
    <date dateType="Issued">2025-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/282971</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1016/j.bioorg.2024.108078</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">&lt;p&gt;In this study, Diels-Alder reaction was performed to sulfolene and endo/exo-diacetate compounds. After a series of reactions, new conduritol A and F analogs containing oxo-bridge and naphthalene rings in their structures were synthesized. To the starting compound, bromination, elimination, singlet oxygen reaction, acetylation, selective oxidation with osmium tetroxide (OsO4), and m-chloroperbenzoic acid (m-CPBA), re-acetylation, and finally hydrolysis of the compounds by NH3(g)/MeOH reactions were carried out. 1 H NMR, 13 C NMR, IR, and elemental analysis elucidated the structures of all synthesized compounds. The alpha, (1-glucosidase, and alpha-amylase inhibitory potentials of the new polycyclitols, conduritol A and F analogs, were examined for biological activity. Also, enzyme kinetic studies of well-active compounds were carried out. Compound 30 showed the best inhibition activity against alpha, (1-glucosidase, and alpha-amylase enzymes. Compound 28a showed the best activity against L929 and Capan-1 cell lines, and compound 22 showed the best activity against the A549 fibroblast cell line. Moreover, hemolysis (ASTM F756 standard) and genotoxicity test results were recorded.&lt;/p&gt;</description>
  </descriptions>
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