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.
Preparation of diazabicyclo[4.3.0]nonene-based peptidomimetics. Publishing Authors By Initials
Preparation of diazabicyclo[4.3.0]nonene-based peptidomimetics. Journal Published:
PUBLICATION TYPE: Research Support, N.I.H., Extr
Journal: The Journal of organic chemistry
VOLUME: 72
Page Numbers: 6865-72
Journal Abbreviation: J. Org. Chem.
ISSN: 0022-3263
DAY: 8
MONTH: 08
YEAR: 2007
Preparation of diazabicyclo[4.3.0]nonene-based peptidomimetics. Information
Number of References:
LANGUAGE: eng
NlmUniqueID: 2985193
Preparation of diazabicyclo[4.3.0]nonene-based peptidomimetics. Keywords Mesh Terms:
KEYWORDS: Peptides
MESH TERMS: chemistry
Chemical & Substance for Abstract: Preparation of diazabicyclo[4.3.0]nonene-based peptidomimetics. Information
Substance Name: 1,5-diazabicyclo(4.3.0)non-5-ene
Registry Number: 3001-72-7
Grant and Affiliation Information for Preparation of diazabicyclo[4.3.0]nonene-based peptidomimetics.
AFFILIATION: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, VIC 3010, Australia. chutton@unimelb.edu.au
Country: United States
AGENCY: United States NIGMS
GRANT: GM-28965
ACRONYM: GM
MEDLINETA: J Org Chem
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