Universität zu Köln

Griesbeck, Axel G. ORCID: 0000-0002-6546-3482, Maassen, Andreas ORCID: 0000-0002-1446-0994, Braeutigam, Maria and Pietsch, Markus (2015). Model Studies on Peroxidic Glutathione Transferase (GST) Inhibitors: C5-Methylated 1,2,4-Trioxanes with C6-Acrylate Side Chains. Eur. J. Org. Chem., 2015 (20). S. 4349 - 4353. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

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Abstract

The 1,2-hydroxy hydroperoxide 7 was obtained with high threo diastereoselectivity from the ester-conjugated allylic alcohol 6 through a porphyrin-sensitized singlet oxygen ene reaction. Compound 7 was used as substrate for peroxy(trans) acetalization with aldehydes, orthoesters, and acetals, catalyzed by boron and indium Lewis acids, as well as by PPTS as a Bronsted acid catalyst (for trioxane 10). The 1,2,4-trioxane 8 was formed with high diasteroselectivity with all-equatorially positioned substitutents at C-3, C-5, and C-6. Additionally, perorthoester 9 was obtained by indium(III)-catalyzed condensation of an orthoester with the hydroperoxide 7. The new compounds 8 and 9 exhibited moderate inhibition of human placental glutathione transferase (GST), comparable to that shown by the 5-unsubstituted model trioxane 11.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Griesbeck, Axel G. UNSPECIFIED orcid.org/0000-0002-6546-3482 UNSPECIFIED Maassen, Andreas UNSPECIFIED orcid.org/0000-0002-1446-0994 UNSPECIFIED Braeutigam, Maria UNSPECIFIED UNSPECIFIED UNSPECIFIED Pietsch, Markus UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-399451
DOI:	10.1002/ejoc.201500326
Journal or Publication Title:	Eur. J. Org. Chem.
Volume:	2015
Number:	20
Page Range:	S. 4349 - 4353
Date:	2015
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1099-0690
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language ALLYLIC ALCOHOLS; S-TRANSFERASES; PHOTOOXYGENATION; ARTEMISININ; ACID Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/39945