A Study on the Chemistry and Biological Activity of 26-Sulfur Analogs of Diosgenin: Synthesis of 26-Thiodiosgenin <i>S</i>-Mono- and Dioxides, and Their Alkyl Derivatives
Aneta M. Tomkiel,
Dorota Czajkowska-Szczykowska,
Ewa Olchowik-Grabarek,
Lucie Rárová,
Szymon Sękowski,
Jacek W. Morzycki
Affiliations
Aneta M. Tomkiel
Laboratory of Natural Products, Department of Organic Chemistry, Faculty of Chemistry, University of Bialystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland
Dorota Czajkowska-Szczykowska
Laboratory of Natural Products, Department of Organic Chemistry, Faculty of Chemistry, University of Bialystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland
Ewa Olchowik-Grabarek
Laboratory of Molecular Biophysics, Department of Microbiology and Biotechnology, Faculty of Biology, University of Bialystok, K. Ciołkowskiego 1 J, 15-245 Białystok, Poland
Lucie Rárová
Department of Experimental Biology, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-78371 Olomouc, Czech Republic
Szymon Sękowski
Laboratory of Molecular Biophysics, Department of Microbiology and Biotechnology, Faculty of Biology, University of Bialystok, K. Ciołkowskiego 1 J, 15-245 Białystok, Poland
Jacek W. Morzycki
Laboratory of Natural Products, Department of Organic Chemistry, Faculty of Chemistry, University of Bialystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland
A chemoselective procedure for MCPBA oxidation of 26-thiodiosgenin to corresponding sulfoxides and sulfone was elaborated. An unusual equilibration of sulfoxides in solution was observed. Moreover, α-alkylation of sulfoxide and sulfone was investigated. Finally, the biological activity of obtained compounds was examined.
