Acid-Catalyzed E-Ring Expansion and Isomerization of 3-Acetylbetulin: Synthesis of Cytotoxic Anhydrobetulin Saponins

Autor:	Jean Legault, Jimmy Bouchard, Charles Gauthier, Dominic Thibeault, André Pichette, Serge Lavoie
Rok vydání:	2009
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Olefin fiber Betulin Glycosylation Trimethylsilyl trifluoromethanesulfonate chemistry Alkene Stereochemistry Organic Chemistry Cytotoxic T cell Cytotoxicity Isomerization
Zdroj:	Synthetic Communications. 40:213-221
ISSN:	1532-2432 0039-7911
Popis:	22(17 → 28)abeo-Lupene derivatives 5a and 6a were obtained after the acid-catalyzed E-ring expansion of 3-acetylbetulin (1a). Glycosylation of these dehydrated triterpenoids using Schmidt's trichloroacetimidate sugar donors in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) provided the new anhydrobetulin saponins 7b–7e in which the terminal olefin C-20(29) isomerizes to form a C-19 tetrasubstituted alkene. The preliminary cytotoxic evaluation revealed that saponins 7b–7d exhibited a moderate cytotoxic activity against A549, DLD-1, and WS1 human cell lines with IC50 ranging from 22 to 49 μM.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::18d7314d0c3efdb07a7f3ca702f663c6 https://doi.org/10.1080/00397910902962886 Zobrazit plný text záznamu