Synthesis and biological evaluation of triterpenoid thiazoles derived from betulonic acid, dihydrobetulonic acid, and ursonic acid

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F20%3A73603809" target="_blank" >RIV/61989592:15110/20:73603809 - isvavai.cz</a>

Alternative codes found

RIV/61989592:15310/20:73603809

Result on the web

<a href="https://www.sciencedirect.com/science/article/pii/S0223523419309584" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0223523419309584</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.ejmech.2019.111806" target="_blank" >10.1016/j.ejmech.2019.111806</a>

Result language

angličtina

Original language name

Synthesis and biological evaluation of triterpenoid thiazoles derived from betulonic acid, dihydrobetulonic acid, and ursonic acid

Original language description

In this work, 35 new derivatives of betulonic, dihydrobetulonic and ursonic acid were prepared including 30 aminothiazoles and all of them were tested for their in vitro cytotoxic activity in eight cancer cell lines and two non-cancer fibroblasts. Compounds with the IC50 below 5 mu M in CCRF-CEM cells and low toxicity in non-cancer fibroblasts (4m, Sc, 5m, 6c, 6m, 7b, and 7c) were further subjected to tests of pharmacological parameters yielding the final set for advanced biological evaluation (4m, 5m, 6m, and 7b). It was proved by several methods, that all of them trigger apoptosis via the intrinsic pathway and derivatives 5m and 7b are the most effective (IC50 2.4 mu M and 3.6 They are the best candidates to become potentially new anticancer drugs and will be subjected to in vivo tests in mice. In addition, compounds 6b and 6c deserve more attention because their activity is not limited only to chemosensitive CCRF-CEM cell line. Specifically, compound 6b is highly active against K562 leukemic cell line (0.7 mu M) and its IC50 activity in colon cancer HCT116 cell line is 1.0 mu M. Compound 6c is active in both normal K562 and resistant K562-TAX cell lines (IC50 3.4 mu M and 5.4 mu M) and both colon cancer cell lines (HCT116 and HCT116p53(-/-) , IC(50)3.5 mu M and 3.4 mu M).

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

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

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2020

Confidentiality

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

Name of the periodical

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

ISSN

0223-5234

e-ISSN

—

Volume of the periodical

185

Issue of the periodical within the volume

JAN

Country of publishing house

FR - FRANCE

Number of pages

18

Pages from-to

"111806-1"-"111806-18"

UT code for WoS article

000503099900027

EID of the result in the Scopus database

2-s2.0-85074176113