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Statements

Subject Item
n2:RIV%2F61989592%3A15310%2F12%3A33138693%21RIV13-MSM-15310___
rdf:type
n3:Vysledek skos:Concept
dcterms:description
The aim of this work was to synthesize a set of heterocyclic derivatives of lupane, lup-20(29)-ene, and 18a-oleanane, and to investigate their cytotoxic activities. Some of those heterocycles were previously known in the oleanane (allobetulin) group; however, to our knowledge the syntheses and biological activities of lupane heterocycles have not been reported before. Starting from betulin (1) and betulinic acid (2), we prepared 3-oxo compounds and 2-bromo-3-oxo compounds 3-10, 2-hydroxymethylene-3-oxo compounds 11-13 and b-oxo esters 14-16. Condensation of these intermediates with hydrazine,phenylhydrazine, hydroxylamine, or thiourea yielded the pyrazole and phenylpyrazole derivatives 17-22, pyrazolones 23-25, isoxazoles 26 and 27, and thiazoles 28-31. Fifteen compounds (14-16, 18-25,and 29-32) have not been reported before. The cytotoxicity was measured using panel of seven cancer cell lines with/without MDR phenotype and non tumor MRC-5 and BJ fibroblasts. The preferential cytotoxicity to cancer cell lines, particularly to hematological tumors was observed, the bromo acids 5, 6 showed highest activity and selectivity against tumor cells. The aim of this work was to synthesize a set of heterocyclic derivatives of lupane, lup-20(29)-ene, and 18a-oleanane, and to investigate their cytotoxic activities. Some of those heterocycles were previously known in the oleanane (allobetulin) group; however, to our knowledge the syntheses and biological activities of lupane heterocycles have not been reported before. Starting from betulin (1) and betulinic acid (2), we prepared 3-oxo compounds and 2-bromo-3-oxo compounds 3-10, 2-hydroxymethylene-3-oxo compounds 11-13 and b-oxo esters 14-16. Condensation of these intermediates with hydrazine,phenylhydrazine, hydroxylamine, or thiourea yielded the pyrazole and phenylpyrazole derivatives 17-22, pyrazolones 23-25, isoxazoles 26 and 27, and thiazoles 28-31. Fifteen compounds (14-16, 18-25,and 29-32) have not been reported before. The cytotoxicity was measured using panel of seven cancer cell lines with/without MDR phenotype and non tumor MRC-5 and BJ fibroblasts. The preferential cytotoxicity to cancer cell lines, particularly to hematological tumors was observed, the bromo acids 5, 6 showed highest activity and selectivity against tumor cells.
dcterms:title
Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid
skos:prefLabel
Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid
skos:notation
RIV/61989592:15310/12:33138693!RIV13-MSM-15310___
n3:predkladatel
n14:orjk%3A15310
n4:aktivita
n15:S n15:P
n4:aktivity
P(ED0030/01/01), P(GA305/09/1216), P(GP301/09/P433), S
n4:cisloPeriodika
11
n4:dodaniDat
n16:2013
n4:domaciTvurceVysledku
n13:8434573
n4:druhVysledku
n12:J
n4:duvernostUdaju
n18:S
n4:entitaPredkladatele
n19:predkladatel
n4:idSjednocenehoVysledku
129385
n4:idVysledku
RIV/61989592:15310/12:33138693
n4:jazykVysledku
n9:eng
n4:klicovaSlova
bromination; triterpenes; isoxazoles; pyrazoles; diazotization; cytotoxicity; heterocycles; oleanane; lupane
n4:klicoveSlovo
n5:lupane n5:heterocycles n5:isoxazoles n5:bromination n5:pyrazoles n5:oleanane n5:cytotoxicity n5:triterpenes n5:diazotization
n4:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n4:kontrolniKodProRIV
[6EF11FB06897]
n4:nazevZdroje
Bioorganic & Medicinal Chemistry
n4:obor
n8:CC
n4:pocetDomacichTvurcuVysledku
1
n4:pocetTvurcuVysledku
5
n4:projekt
n11:ED0030%2F01%2F01 n11:GP301%2F09%2FP433 n11:GA305%2F09%2F1216
n4:rokUplatneniVysledku
n16:2012
n4:svazekPeriodika
20
n4:tvurceVysledku
Šarek, Jan Urban, Milan Vlk, Martin Džubák, Petr Hajdúch, Marián
s:issn
0968-0896
s:numberOfPages
9
n17:organizacniJednotka
15310