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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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  <dc:creator>Aydin, Gokay</dc:creator>
  <dc:creator>Coban, Canan cakir</dc:creator>
  <dc:creator>Kurbanoglu, N. Izzet</dc:creator>
  <dc:creator>Turk, Mustafa</dc:creator>
  <dc:creator>Baran, Arif</dc:creator>
  <dc:date>2025-01-01</dc:date>
  <dc:description>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.</dc:description>
  <dc:identifier>https://aperta.ulakbim.gov.trrecord/282971</dc:identifier>
  <dc:identifier>oai:aperta.ulakbim.gov.tr:282971</dc:identifier>
  <dc:rights>info:eu-repo/semantics/openAccess</dc:rights>
  <dc:rights>http://www.opendefinition.org/licenses/cc-by</dc:rights>
  <dc:source>BIOORGANIC CHEMISTRY 154 23</dc:source>
  <dc: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</dc:title>
  <dc:type>info:eu-repo/semantics/article</dc:type>
  <dc:type>publication-article</dc:type>
</oai_dc:dc>
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