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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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        "affiliation": "Karamanoglu Mehmetbey Univ, Vocat Sch Healty Serv, TR-70200 Karaman, Turkiye", 
        "name": "Aydin, Gokay"
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      {
        "affiliation": "Karadeniz Tech Univ, Acad Data Management Syst, TR-61080 Trabzon, Turkiye", 
        "name": "Coban, Canan cakir"
      }, 
      {
        "affiliation": "Sakarya Univ, Fac Educ, Dept Math & Sci Educ, TR-54050 Sakarya, Turkiye", 
        "name": "Kurbanoglu, N. Izzet"
      }, 
      {
        "affiliation": "Kirikkale Univ, Fac Engn & Architecture, Bioengn Dept, TR-71451 Kirikkale, Turkiye", 
        "name": "Turk, Mustafa"
      }, 
      {
        "affiliation": "Sakarya Univ, Fac Arts & Sci, Chem Dept, TR-54050 Sakarya, Turkiye", 
        "name": "Baran, Arif"
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    "description": "<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>", 
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      "title": "BIOORGANIC CHEMISTRY", 
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    "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"
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