Universität zu Köln

Hirschhaeuser, Christoph, Velcicky, Juraj ORCID: 0000-0001-6564-1448, Schlawe, Daniel, Hessler, Erik, Majdalani, Andre, Neudoerfl, Joerg-Martin, Prokop, Aram, Wieder, Thomas and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2013). Nucleoside Analogues with a 1,3-Diene-Fe(CO)(3) Substructure: Stereoselective Synthesis, Configurational Assignment, and Apoptosis-Inducing Activity. Chem.-Eur. J., 19 (39). S. 13017 - 13030. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

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Abstract

The synthesis and stereochemical assignment of two classes of iron-containing nucleoside analogues, both of which contain a butadieneFe(CO)(3) substructure, is described. The first type of compounds are Fe(CO)(3)-complexed 3-alkenyl-2,3-dideoxy-2,3-dehydro nucleosides (2,5-dihydrofuran derivatives), from which the second class of compounds is derived by formal replacement of the ring oxygen atom by a CH2 group (carbocyclic nucleoside analogues). These compounds were prepared in a stereoselective manner through the metal-assisted introduction of the nucleobase. Whilst the furanoid intermediates were prepared from carbohydrates (such as methyl-glucopyranoside), the carbocyclic compounds were obtained by using an intramolecular Pauson-Khand reaction. Stereochemical assignments based on NMR and CD spectroscopy were confirmed by X-ray structural analysis. Biological investigations revealed that several of the complexes exhibited pronounced apoptosis-inducing properties (through an unusual caspase 3-independent but ROS-dependent pathway). Furthermore, some structure-activity relationships were identified, also as a precondition for the design and synthesis of fluorescent and biotin-labeled conjugates.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Hirschhaeuser, Christoph UNSPECIFIED UNSPECIFIED UNSPECIFIED Velcicky, Juraj UNSPECIFIED orcid.org/0000-0001-6564-1448 UNSPECIFIED Schlawe, Daniel UNSPECIFIED UNSPECIFIED UNSPECIFIED Hessler, Erik UNSPECIFIED UNSPECIFIED UNSPECIFIED Majdalani, Andre UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Prokop, Aram UNSPECIFIED UNSPECIFIED UNSPECIFIED Wieder, Thomas UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-475755
DOI:	10.1002/chem.201301672
Journal or Publication Title:	Chem.-Eur. J.
Volume:	19
Number:	39
Page Range:	S. 13017 - 13030
Date:	2013
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3765
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language PAUSON-KHAND REACTION; ORGANOMETALLIC COMPLEXES; BIOORGANOMETALLIC CHEMISTRY; BORANE REDUCTION; MECHANISM; (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE; RESOLUTION; SERIES Multiple languages Chemistry, Multidisciplinary Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/47575