volume 3 issue 6 pages 865-868

3,8-Diazabicyclo[3.2.1]octan-2-one peptide mimetics: synthesis of a conformationally restricted inhibitor of farnesyltransferase.

Christopher J Dinsmore 1
Jeffrey M Bergman 1
Michael J. Bogusky 1
J.Christopher Culberson 1
Kelly A. Hamilton 1
Samuel L. Graham 1
1
 
Departments of Medicinal Chemistry, Molecular Systems, and Cancer Research, Merck Research Laboratories, P.O. Box 4, West Point, Pennsylvania 19486
Publication typeJournal Article
Publication date2001-02-17
scimago Q1
wos Q1
SJR1.235
CiteScore8.7
Impact factor5.0
ISSN15237060, 15237052
PubMed ID:  11263902
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A new synthesis of the 3,8-diazabicyclo[3.2.1]octan-2-one framework is described. Transannular enolate alkylation of piperazinone derivatives provides a flexible route to highly constrained bicyclic peptidomimetic synthons with substitution at the Calpha position. The chemistry was used to produce a conformationally constrained farnesyltransferase inhibitor, which aided the elucidation of enzyme-bound conformation.
Found 
Found 

Top-30

Journals

1
2
3
4
5
Tetrahedron Letters
5 publications, 17.24%
Tetrahedron Asymmetry
3 publications, 10.34%
Russian Journal of Organic Chemistry
2 publications, 6.9%
Organic Letters
2 publications, 6.9%
Bioorganic and Medicinal Chemistry Letters
2 publications, 6.9%
Tetrahedron
2 publications, 6.9%
Journal of Organic Chemistry
2 publications, 6.9%
Organic and Biomolecular Chemistry
2 publications, 6.9%
Journal of Heterocyclic Chemistry
1 publication, 3.45%
Angewandte Chemie
1 publication, 3.45%
Angewandte Chemie - International Edition
1 publication, 3.45%
Organic Preparations and Procedures International
1 publication, 3.45%
Synthetic Communications
1 publication, 3.45%
Heterocycles
1 publication, 3.45%
Synlett
1 publication, 3.45%
1
2
3
4
5

Publishers

2
4
6
8
10
12
Elsevier
12 publications, 41.38%
American Chemical Society (ACS)
4 publications, 13.79%
Wiley
3 publications, 10.34%
Pleiades Publishing
2 publications, 6.9%
Royal Society of Chemistry (RSC)
2 publications, 6.9%
Taylor & Francis
2 publications, 6.9%
The Japan Institute of Heterocyclic Chemistry
1 publication, 3.45%
Georg Thieme Verlag KG
1 publication, 3.45%
2
4
6
8
10
12
  • We do not take into account publications without a DOI.
  • Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
29
Share
Cite this
GOST |
Cite this
GOST Copy
Dinsmore C. J. et al. 3,8-Diazabicyclo[3.2.1]octan-2-one peptide mimetics: synthesis of a conformationally restricted inhibitor of farnesyltransferase. // Organic Letters. 2001. Vol. 3. No. 6. pp. 865-868.
GOST all authors (up to 50) Copy
Dinsmore C. J., Bergman J. M., Bogusky M. J., Culberson J., Hamilton K. A., Graham S. L. 3,8-Diazabicyclo[3.2.1]octan-2-one peptide mimetics: synthesis of a conformationally restricted inhibitor of farnesyltransferase. // Organic Letters. 2001. Vol. 3. No. 6. pp. 865-868.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/ol015504w
UR - https://doi.org/10.1021/ol015504w
TI - 3,8-Diazabicyclo[3.2.1]octan-2-one peptide mimetics: synthesis of a conformationally restricted inhibitor of farnesyltransferase.
T2 - Organic Letters
AU - Dinsmore, Christopher J
AU - Bergman, Jeffrey M
AU - Bogusky, Michael J.
AU - Culberson, J.Christopher
AU - Hamilton, Kelly A.
AU - Graham, Samuel L.
PY - 2001
DA - 2001/02/17
PB - American Chemical Society (ACS)
SP - 865-868
IS - 6
VL - 3
PMID - 11263902
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2001_Dinsmore,
author = {Christopher J Dinsmore and Jeffrey M Bergman and Michael J. Bogusky and J.Christopher Culberson and Kelly A. Hamilton and Samuel L. Graham},
title = {3,8-Diazabicyclo[3.2.1]octan-2-one peptide mimetics: synthesis of a conformationally restricted inhibitor of farnesyltransferase.},
journal = {Organic Letters},
year = {2001},
volume = {3},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/ol015504w},
number = {6},
pages = {865--868},
doi = {10.1021/ol015504w}
}
MLA
Cite this
MLA Copy
Dinsmore, Christopher J., et al. “3,8-Diazabicyclo[3.2.1]octan-2-one peptide mimetics: synthesis of a conformationally restricted inhibitor of farnesyltransferase..” Organic Letters, vol. 3, no. 6, Feb. 2001, pp. 865-868. https://doi.org/10.1021/ol015504w.