Synthesis and Cytotoxicity of 28a-Homothiolupanes and 28a-Homothiolupane Saponins

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F16%3A00457676" target="_blank" >RIV/61389030:_____/16:00457676 - isvavai.cz</a>

Alternative codes found

RIV/61989592:15310/16:33162007

Result on the web

<a href="http://dx.doi.org/10.1002/ejoc.201501147" target="_blank" >http://dx.doi.org/10.1002/ejoc.201501147</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.201501147" target="_blank" >10.1002/ejoc.201501147</a>

Result language

angličtina

Original language name

Synthesis and Cytotoxicity of 28a-Homothiolupanes and 28a-Homothiolupane Saponins

Original language description

A concise synthesis of 28a-homo-28a-thiolupane triterpenes and the corresponding saponins containing D-mannose, D-idose, L-arabinose and L-rhamnose moieties was elaborated. New triterpenes were obtained from readily available 3-O-allylbetulinal by elongation of the carbon chain by Wittig reaction, followed by hydrolysis of the enol ether, reduction of the elongated aldehyde and nucleophilic substitution of the corresponding mesylate with thiocyanate ion. Saponins were obtained by glycosylation of triterpenes with classical Schmidt donors. The cytotoxic activities of the new homothiolupane compounds were evaluated in vitro, revealing that some triterpenes and the corresponding saponins exhibited interesting cytotoxic activity profiles against human cancer cell lines. An unexpected influence of the allyl protecting group on the cytotoxicity of homothiobetulin derivatives was revealed. These results open the way to the synthesis of various lupane-type derivatives containing sulfur in the

Czech name

—

Czech description

—

Type

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

CEP classification

EB - Genetics and molecular biology

OECD FORD branch

—

Project

<a href="/en/project/LO1204" target="_blank" >LO1204: Sustainable development of research in the Centre of the Region Haná</a><br>

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

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

—

Volume of the periodical

—

Issue of the periodical within the volume

2

Country of publishing house

DE - GERMANY

Number of pages

11

Pages from-to

373-383

UT code for WoS article

000368814900020

EID of the result in the Scopus database

—