Enantioselective Synthesis of Ferrocenyl Nucleoside Analogues with Apoptosis-Inducing Activity
2006; American Chemical Society; Volume: 8; Issue: 13 Linguagem: Inglês
10.1021/ol060868f
ISSN1523-7060
AutoresPhilippe James, Jörg‐M. Neudörfl, Moritz F. Eissmann, Patrick Jesse, Aram Prokop, Hans‐Günther Schmalz,
Tópico(s)Metal complexes synthesis and properties
ResumoAs a contribution to bioorganometallic chemistry, an enantioselective synthesis of novel carbocyclic nucleoside analogues with a ferroceno-cyclopentene backbone was developed. Diastereoselective cuprate 1,4-addition or Mukaiyama−Michael addition to a planar-chiral enoate (ethyl (E)-2-[2-methoxycarbonyl-ferrocenyl]-acrylate) allowed for the introduction of different side chains (RCH2). Other important steps include a Dieckmann cyclization and the attachment of the nucleobase (NB) in an iron-assisted SN1 reaction. Some of the target compounds were shown to exhibit significant apoptosis-inducing activity (LD50 = 10−20 μM) against tumor cells.
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