A Study on the Chemistry and Biological Activity of 26-Sulfur Analogs of Diosgenin: Synthesis of 26-Thiodiosgenin S -Mono- and Dioxides, and Their Alkyl Derivatives

A Study on the Chemistry and Biological Activity of 26-Sulfur Analogs of Diosgenin: Synthesis of 26-Thiodiosgenin S -Mono- and Dioxides, and Their Alkyl Derivatives

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 c...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2022-12, Vol.28 (1), p.189
Hauptverfasser: Tomkiel, Aneta M, Czajkowska-Szczykowska, Dorota, Olchowik-Grabarek, Ewa, Rárová, Lucie, Sękowski, Szymon, Morzycki, Jacek W
Format: Artikel
Sprache:eng
Schlagworte:
26-thiodiosgenin
Alkylation
Antimicrobial agents
Biological activity
Cancer
Chemical activity
Chemistry
Hydrogen peroxide
Oxidation
Reagents
sapogenins
Steroids
sulfones
Sulfoxides
Sulfur
thiol oxidation
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Zusammenfassung: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28010189