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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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{
  "DOI": "10.1016/j.bioorg.2024.108078", 
  "abstract": "<p>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.</p>", 
  "author": [
    {
      "family": "Aydin", 
      "given": " Gokay"
    }, 
    {
      "family": "Coban", 
      "given": " Canan cakir"
    }, 
    {
      "family": "Kurbanoglu", 
      "given": " N. Izzet"
    }, 
    {
      "family": "Turk", 
      "given": " Mustafa"
    }, 
    {
      "family": "Baran", 
      "given": " Arif"
    }
  ], 
  "container_title": "BIOORGANIC CHEMISTRY", 
  "id": "282971", 
  "issued": {
    "date-parts": [
      [
        2025, 
        1, 
        1
      ]
    ]
  }, 
  "page": "23", 
  "title": "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", 
  "type": "article-journal", 
  "volume": "154"
}
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