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
|
Тип публикации: Journal Article
Дата публикации: 2001-02-17
scimago Q1
wos Q1
БС1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
11263902
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
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.
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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.
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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.
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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 -
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@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}
}
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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.