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

Result code in 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>

Alternative codes found

RIV/61989592:15310/16:33162004

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CE - Biochemistry

OECD FORD branch

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Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2016

Confidentiality

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

Name of the periodical

Organic & Biomolecular Chemistry

ISSN

1477-0520

e-ISSN

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Volume of the periodical

14

Issue of the periodical within the volume

43

Country of publishing house

GB - UNITED KINGDOM

Number of pages

11

Pages from-to

10238-10248

UT code for WoS article

000387902900017

EID of the result in the Scopus database

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