Počet záznamů: 1
Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain
- 1.
SYSNO ASEP 0429932 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Synthesis and structure-activity relationship study of cytotoxic lupane-type 3 beta-O-monodesmosidic saponins with an extended C-28 side chain Tvůrce(i) Cmoch, P. (PL)
Korda, A. (PL)
Rárová, Lucie (UEB-Q) RID, ORCID
Oklešťková, Jana (UEB-Q) RID, ORCID, SAI
Strnad, Miroslav (UEB-Q) RID, ORCID
Luboradzki, R. (PL)
Pakulski, Z. (PL)Zdroj.dok. Tetrahedron. - : Elsevier - ISSN 0040-4020
Roč. 70, č. 17 (2014), s. 2717-2730Poč.str. 14 s. Jazyk dok. eng - angličtina Země vyd. GB - Velká Británie Klíč. slova BETULIN DERIVATIVES ; SECONDARY ALCOHOLS ; ANTITUMOR-ACTIVITY Vědní obor RIV EB - Genetika a molekulární biologie CEP LO1204 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy Institucionální podpora UEB-Q - RVO:61389030 UT WOS 000334132800005 DOI 10.1016/j.tet.2014.03.006 Anotace A concise synthesis of lupane triterpenes with an elongated carbon chain at the C-28 position, as well as saponins containing D-mannose, L-arabinose, and L-rhamnose moieties at the C-3 position is described. The overall synthesis of the new triterpenes involved seven linear steps starting from natural betulin: selective protection of a hydroxyl group, oxidation, elongation of the carbon chain by Grignard reaction, and deoxygenation. O-Glycosides were obtained by glycosylation of triterpenes with classical Schmidt's donors. Additionally, all new compounds were evaluated in vitro for their cytotoxic activities. Several triterpenes and the corresponding saponins exhibited an interesting cytotoxic activity profile against human cancer cell lines. The therapeutical index of active triterpenes is very high, since almost none of them were cytotoxic for normal BJ fibroblasts. These results open the way to the synthesis of various lupane-type saponin derivatives as potentially bioactive compounds. Pracoviště Ústav experimentální botaniky Kontakt David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469 Rok sběru 2015
Počet záznamů: 1