About: Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
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. (en)
Title	Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid (en)
skos:prefLabel	Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid (en)
skos:notation	RIV/61989592:15310/12:33138693!RIV13-MSM-15310___
http://linked.open...avai/riv/aktivita	P S
http://linked.open...avai/riv/aktivity	P(ED0030/01/01), P(GA305/09/1216), P(GP301/09/P433), S
http://linked.open...iv/cisloPeriodika	11
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Šarek, Jan
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Palackého v Olomouci / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	129385
http://linked.open...ai/riv/idVysledku	RIV/61989592:15310/12:33138693
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	bromination; triterpenes; isoxazoles; pyrazoles; diazotization; cytotoxicity; heterocycles; oleanane; lupane (en)
http://linked.open.../riv/klicoveSlovo	cytotoxicity lupane bromination diazotization isoxazoles oleanane pyrazoles triterpenes heterocycles
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[6EF11FB06897]
http://linked.open...i/riv/nazevZdroje	Bioorganic & Medicinal Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	5 (xsd:int)
http://linked.open...vavai/riv/projekt	Biomedicine for regional development and human resources Study of mechnism of action and structure optimalization of triterpenoids with anti-tumor activity. Betulinic acid derivatives, identification of mechanism of anticancer action based on expression profiling.
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	20
http://linked.open...iv/tvurceVysledku	Džubák, Petr Hajdúch, Marián Vlk, Martin Šarek, Jan Urban, Milan
issn	0968-0896
number of pages	9 (xsd:int)
http://localhost/t...ganizacniJednotka	15310

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