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

doi:10.3390/molecules28010189

Molecules (Dec 2022)

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

DOI: https://doi.org/10.3390/molecules28010189
Journal volume & issue: Vol. 28, no. 1
p. 189

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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