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

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. ¹H NMR, ¹³C NMR, IR, and elemental analysis elucidated the structures of all synthesized compounds. The α, β-glucosidase, and α-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 α, β-glucosidase, and α-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.