Synthesis and Pharmacological Effects of Diosgenin-Betulinic Acid Conjugates

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F20%3A43920394" target="_blank" >RIV/60461373:22330/20:43920394 - isvavai.cz</a>

Alternative codes found

RIV/61389030:_____/20:00531907 RIV/61388963:_____/20:00531907 RIV/68407700:21340/20:00342222 RIV/61989592:15310/20:73604744

Result on the web

<a href="https://www.mdpi.com/1420-3049/25/15/3546/htm" target="_blank" >https://www.mdpi.com/1420-3049/25/15/3546/htm</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/molecules25153546" target="_blank" >10.3390/molecules25153546</a>

Result language

angličtina

Original language name

Synthesis and Pharmacological Effects of Diosgenin-Betulinic Acid Conjugates

Original language description

The target diosgenin-betulinic acid conjugates are reported to investigate their ability to enhance and modify the pharmacological effects of their components. The detailed synthetic procedure that includes copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition (click reaction), and palladium-catalyzed debenzylation by hydrogenolysis is described together with the results of cytotoxicity screening tests. Palladium-catalyzed debenzylation reaction of benzyl ester intermediates was the key step in this synthetic procedure due to the simultaneous presence of a 1,4-disubstituted 1,2,3-triazole ring in the molecule that was a competing coordination site for the palladium catalyst. High pressure (130 kPa) palladium-catalyzed procedure represented a successful synthetic step yielding the required products. The conjugate7showed selective cytotoxicity in human T-lymphoblastic leukemia (CEM) cancer cells (IC50= 6.5 +/- 1.1 mu M), in contrast to the conjugate8showing no cytotoxicity, and diosgenin (1), an adaptogen, for which a potential to be active on central nervous system was calculated in silico. In addition,5showed medium multifarious cytotoxicity in human T-lymphoblastic leukemia (CEM), human cervical cancer (HeLa), and human colon cancer (HCT 116). Betulinic acid (2) and the intermediates3and4showed no cytotoxicity in the tested cancer cell lines. The experimental data obtained are supplemented by and compared with the in silico calculated physico-chemical and absorption, distribution, metabolism, and excretion (ADME) parameters of these compounds.

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

Molecules

ISSN

1420-3049

e-ISSN

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Volume of the periodical

25

Issue of the periodical within the volume

15

Country of publishing house

CH - SWITZERLAND

Number of pages

14

Pages from-to

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UT code for WoS article

000559001100001

EID of the result in the Scopus database

2-s2.0-85089171176