Gutenberg Open Science: Electrosynthesis of stable betulin-derived nitrile oxides and their application in synthesis of cytostatic lupane-type triterpenoid-isoxazole conjugates

Please use this identifier to cite or link to this item: http://doi.org/10.25358/openscience-8089

Full metadata record

DC Field	Value	Language
dc.contributor.author	Lugiņina, Jevgeņija	-
dc.contributor.author	Linden, Martin	-
dc.contributor.author	Bazulis, Māris	-
dc.contributor.author	Kumpiņš, Viktors	-
dc.contributor.author	Mishnev, Anatoly	-
dc.contributor.author	Popov, Sergey A.	-
dc.contributor.author	Golubeva, Tatiana S.	-
dc.contributor.author	Waldvogel, Siegfried R.	-
dc.contributor.author	Shults, Elvira E.	-
dc.contributor.author	Turks, Māris	-
dc.date.accessioned	2022-11-15T10:46:29Z	-
dc.date.available	2022-11-15T10:46:29Z	-
dc.date.issued	2021	-
dc.identifier.uri	https://openscience.ub.uni-mainz.de/handle/20.500.12030/8104	-
dc.description.abstract	Novel lupane-type triterpenoid-isoxazole conjugates were designed by direct placing of isoxazole linker at C(17) of triterpenoid. The suggested synthetic sequence demonstrates successful combination of electro-organic synthesis and conventional approaches. TEMPO-mediated electrooxidation of betulin to betulinal was developed and optimized at boron-doped diamond anodes with potassium acetate as inexpensive supporting electrolyte. Betulinal-derived oxime was further selectively electro-oxidized at a graphite anode to nitrile oxide, which proved to be stable and isolable species. The same reaction sequence was performed with 3β-lupane-3,28-diol. Nitrile oxides were characterized by 15N NMR and X-ray crystallography. The isolable nitrile oxides allowed creation of isoxazole library by 1,3-dipolar cycloaddition reactions with various alkynes. Some of the title conjugates exhibit cytostatic properties against breast cancer cell line MCF7, glioblastoma multiform cell line U-87 MG and lung carcinoma cell line A549 with growth inhibition (GI50) concentrations up to 11 μm, while being harmless to immortalized human fibroblasts hTERT (GI50 >100 μm).	en_GB
dc.language.iso	eng	de
dc.rights	CC BY	*
dc.rights.uri	https://creativecommons.org/licenses/by/4.0/	*
dc.subject.ddc	540 Chemie	de_DE
dc.subject.ddc	540 Chemistry and allied sciences	en_GB
dc.title	Electrosynthesis of stable betulin-derived nitrile oxides and their application in synthesis of cytostatic lupane-type triterpenoid-isoxazole conjugates	en_GB
dc.type	Zeitschriftenaufsatz	de
dc.identifier.doi	http://doi.org/10.25358/openscience-8089	-
jgu.type.dinitype	article	en_GB
jgu.type.version	Published version	de
jgu.type.resource	Text	de
jgu.organisation.department	FB 09 Chemie, Pharmazie u. Geowissensch.	de
jgu.organisation.number	7950	-
jgu.organisation.name	Johannes Gutenberg-Universität Mainz	-
jgu.rights.accessrights	openAccess	-
jgu.journal.title	European journal of organic chemistry	de
jgu.journal.volume	2021	de
jgu.journal.issue	17	de
jgu.pages.start	2557	de
jgu.pages.end	2577	de
jgu.publisher.year	2021	-
jgu.publisher.name	Wiley-VCH	de
jgu.publisher.place	Weinheim	de
jgu.publisher.issn	1099-0690	de
jgu.organisation.place	Mainz	-
jgu.subject.ddccode	540	de
jgu.publisher.doi	10.1002/ejoc.202100293	de
jgu.organisation.ror	https://ror.org/023b0x485	-
Appears in collections:	JGU-Publikationen

Files in This Item:

	File	Description	Size	Format
	electrosynthesis_of_stable_be-20221115115020172.pdf		881.02 kB	Adobe PDF	View/Open

Show simple item record