Preparation of diazabicyclo[4.3.0]nonene-based peptidomimetics.
Several functionalized diazabicyclo[4.3.0]nonenes and other heterocycles have been prepared as potential peptidomimetic scaffolds. A novel and efficient method has been developed for the preparation of N-substituted gamma-lactams 13. Preparation of amidine-containing 1,5-diazabicyclo[4.3.0]nonenes 43 and 44 has been achieved through Hg-mediated cyclization of the precursor N-aminopropyl-gamma-thiolactams and subsequent functional group manipulation. Bicycle 43 represents a novel scaffold for potential peptide turn mimetics, whereas 44 could potentially be employed as an alpha-helix template attached to the C-terminus of peptides. These compounds are novel additions to the current range of small-molecule constrained peptidomimetics.
Hutton
Craig A
CA
School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, VIC 3010, Australia. chutton@unimelb.edu.au
Bartlett
Paul A
PA
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry*; D032701:Biomimetics; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*
D001372:Aza Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007769:Lactams; D010455:Peptides; C013554:1,5-diazabicyclo(4.3.0)non-5-ene