Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F16%3A00467449" target="_blank" >RIV/61389030:_____/16:00467449 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61989592:15310/16:33162004

Výsledek na webu

<a href="http://dx.doi.org/10.1039/c6ob01938b" target="_blank" >http://dx.doi.org/10.1039/c6ob01938b</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c6ob01938b" target="_blank" >10.1039/c6ob01938b</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins

Popis výsledku v původním jazyce

A practical synthesis of 28a-homo-28a-selenolupane triterpenes and the corresponding selenosaponins containing D-mannose, L-arabinose, L-rhamnose, and D-idose moieties is described. Selenium containing triterpenes were obtained from the readily available 3-O-allyl-homobetulin mesylate by nucleophilic substitution with the selenocyanate ion which upon reduction of theSeCN group afforded the free selenol. Glycosylation using classical Schmidt donors gave 1,2-trans selenosaponins as the main product as well as minute amounts of 1,2-cis isomers. This is one of the very few examples of the synthesis of selenoglycosides by direct glycosylation of free selenols. The studied selenol showed high resistance to air oxidation resulting in good stability during the synthesis of selenolupane derivatives. Cytotoxic activities of new homoselenolupane derivatives were also evaluated in vitro and revealed that some triterpenes exhibited an interesting profile against human cancer cell lines.

Název v anglickém jazyce

Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins

Popis výsledku anglicky

A practical synthesis of 28a-homo-28a-selenolupane triterpenes and the corresponding selenosaponins containing D-mannose, L-arabinose, L-rhamnose, and D-idose moieties is described. Selenium containing triterpenes were obtained from the readily available 3-O-allyl-homobetulin mesylate by nucleophilic substitution with the selenocyanate ion which upon reduction of theSeCN group afforded the free selenol. Glycosylation using classical Schmidt donors gave 1,2-trans selenosaponins as the main product as well as minute amounts of 1,2-cis isomers. This is one of the very few examples of the synthesis of selenoglycosides by direct glycosylation of free selenols. The studied selenol showed high resistance to air oxidation resulting in good stability during the synthesis of selenolupane derivatives. Cytotoxic activities of new homoselenolupane derivatives were also evaluated in vitro and revealed that some triterpenes exhibited an interesting profile against human cancer cell lines.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CE - Biochemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Organic & Biomolecular Chemistry

ISSN

1477-0520

e-ISSN

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Svazek periodika

14

Číslo periodika v rámci svazku

43

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

11

Strana od-do

10238-10248

Kód UT WoS článku

000387902900017

EID výsledku v databázi Scopus

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