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Stereoselective synthesis of (3-aminodecahydro-1,4-methanonaphthalen-2-yl)methanols targeted to the C1 domain of protein kinase C

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
67
Issue
45
Identifiers
DOI: 10.1016/j.tet.2011.09.044
Keywords
  • Diels–Alder Reaction
  • Protein Kinase C
  • Molecular Modeling
  • Curtius–Schmidt Rearrangement
Disciplines
  • Biology
  • Medicine

Abstract

Abstract Protein kinase C (PKC) is a widely studied molecular target for the treatment of cancer and other diseases. We have approached the issue of modifying PKC function by targeting the C1 domain in the regulatory region of the enzyme. By using the X-ray crystal structure of the PKCδ C1b domain combined with molecular modeling, we discovered (3-aminodecahydro-1,4-methanonaphthalen-2-yl)methanol as a novel C1 domain ligand. The stereoselective synthesis of this tricyclic γ-amino alcohol was based on two successive Diels–Alder reactions to construct the six continuous stereocenters of the key intermediate.

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