Synthesis of selectively deuterated and tritiated lupane derivatives

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F13%3A33147739" target="_blank" >RIV/61989592:15310/13:33147739 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61989592:15110/13:33147739

Výsledek na webu

<a href="http://dx.doi.org/10.1007/s10967-013-2533-8" target="_blank" >http://dx.doi.org/10.1007/s10967-013-2533-8</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s10967-013-2533-8" target="_blank" >10.1007/s10967-013-2533-8</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of selectively deuterated and tritiated lupane derivatives

Popis výsledku v původním jazyce

The aim of this work was to synthesize deuterated and tritiated analogues of highly oxidized lupane derivatives known from our group. We selected compounds that previously showed very high cytotoxic activity on multiple cancer cell lines in order to further investigate the mechanism of their action. From starting material (compounds 1-4), we obtained benzyl platanate (5) and its reaction with deuteromethyltriphenylphosphonium iodide gave deuterated compound 6. Following benzyl deprotection gave free acid 7 and oxidation with SeO2 gave 30-oxo-[29-H-2(2)]lup-20(29)-en-28-oic acid (8), which is one of the most active compounds synthesized in our group to date (IC50 6 mu mol/L on CEM cell line). The alkylation of benzyl 2-hydroxy-3-oxolupa-1,20(29)-dien-28-oate (9) with methyliodide or deuteromethyliodide followed by a series of deprotection and hydrogenation steps gave compounds 10-14, where 2 beta-[31-H-2(3)]methoxy-3-oxolupan-20(29)-en-28-oic acid (13) is especially interesting, it show

Název v anglickém jazyce

Synthesis of selectively deuterated and tritiated lupane derivatives

Popis výsledku anglicky

The aim of this work was to synthesize deuterated and tritiated analogues of highly oxidized lupane derivatives known from our group. We selected compounds that previously showed very high cytotoxic activity on multiple cancer cell lines in order to further investigate the mechanism of their action. From starting material (compounds 1-4), we obtained benzyl platanate (5) and its reaction with deuteromethyltriphenylphosphonium iodide gave deuterated compound 6. Following benzyl deprotection gave free acid 7 and oxidation with SeO2 gave 30-oxo-[29-H-2(2)]lup-20(29)-en-28-oic acid (8), which is one of the most active compounds synthesized in our group to date (IC50 6 mu mol/L on CEM cell line). The alkylation of benzyl 2-hydroxy-3-oxolupa-1,20(29)-dien-28-oate (9) with methyliodide or deuteromethyliodide followed by a series of deprotection and hydrogenation steps gave compounds 10-14, where 2 beta-[31-H-2(3)]methoxy-3-oxolupan-20(29)-en-28-oic acid (13) is especially interesting, it show

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/GA305%2F09%2F1216" target="_blank" >GA305/09/1216: Studium mechanismu účinku a optimalizace struktury triterpenoidů s protinádorovou aktivitou.</a><br>

Návaznosti

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

Rok uplatnění

2013

Kód důvěrnosti údajů

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

Název periodika

Journal of Radioanalytical and Nuclear Chemistry

ISSN

0236-5731

e-ISSN

—

Svazek periodika

298

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

HU - Maďarsko

Počet stran výsledku

9

Strana od-do

1149-1157

Kód UT WoS článku

000325624300049

EID výsledku v databázi Scopus

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