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- Title
Nucleoside Analogues with a 1,3-DieneFe(CO)<sub>3</sub> Substructure: Stereoselective Synthesis, Configurational Assignment, and Apoptosis-Inducing Activity.
- Authors
Hirschhäuser, Christoph; Velcicky, Juraj; Schlawe, Daniel; Hessler, Erik; Majdalani, André; Neudörfl, Jörg‐Martin; Prokop, Aram; Wieder, Thomas; Schmalz, Hans‐Günther
- 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.
- Subjects
NUCLEOSIDES; STEREOSELECTIVE reactions; APOPTOSIS; ANTINEOPLASTIC agents; CARBONYL compounds; IRON
- Publication
Chemistry - A European Journal, 2013, Vol 19, Issue 39, p13017
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201301672