Design and synthesis of conformationally constrained 3-(N-alkylamino)propylphosphonic acids as potent agonists of sphingosine-1-phosphate (S1P) receptors
Lin Yan
1
,
Jeffrey J. Hale
1
,
Christopher Lynch
1
,
Richard Budhu
1
,
Amy Gentry
1
,
Sander G. Mills
1
,
Richard Hajdu
2
,
Carol Ann Keohane
2
,
Mark J. Rosenbach
2
,
James E. Milligan
2
,
Gan Ju Shei
2
,
Gary Chrebet
2
,
James Bergstrom
2
,
Deborah Card
2
,
H. ROSEN
2
,
Suzanne M. Mandala
2
1
Department of Medicinal Chemistry, Merck Research Laboratories, PO Box 2000 Rahway, NJ 07065, USA.
|
2
Department of Immunology and Rheumatology, Merck Research Laboratories, PO Box 2000, Rahway, NJ 07065, USA
|
Тип публикации: Journal Article
Дата публикации: 2004-10-01
scimago Q2
wos Q2
БС2
SJR: 0.472
CiteScore: 5.1
Impact factor: 2.2
ISSN: 0960894X, 14643405
PubMed ID:
15341940
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Краткое описание
A series of conformationally constrained 3-(N-alkylamino)propylphosphonic acids were systematically synthesized and their activities as S1P receptor agonists were evaluated. Several pyrrolidine and cyclohexane analogs had S1P receptor profiles comparable to the acyclic lead compound, 3-(N-tetradecylamino)propylphosphonic acid (3), lowered circulating lymphocytes in mice after iv administration and were thus identified as being suitable for further investigations.
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Yan L. et al. Design and synthesis of conformationally constrained 3-(N-alkylamino)propylphosphonic acids as potent agonists of sphingosine-1-phosphate (S1P) receptors // Bioorganic and Medicinal Chemistry Letters. 2004. Vol. 14. No. 19. pp. 4861-4866.
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Yan L., Hale J. J., Lynch C., Budhu R., Gentry A., Mills S. G., Hajdu R., Keohane C. A., Rosenbach M. J., Milligan J. E., Shei G. J., Chrebet G., Bergstrom J., Card D., ROSEN H., Mandala S. M. Design and synthesis of conformationally constrained 3-(N-alkylamino)propylphosphonic acids as potent agonists of sphingosine-1-phosphate (S1P) receptors // Bioorganic and Medicinal Chemistry Letters. 2004. Vol. 14. No. 19. pp. 4861-4866.
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TY - JOUR
DO - 10.1016/j.bmcl.2004.07.049
UR - https://doi.org/10.1016/j.bmcl.2004.07.049
TI - Design and synthesis of conformationally constrained 3-(N-alkylamino)propylphosphonic acids as potent agonists of sphingosine-1-phosphate (S1P) receptors
T2 - Bioorganic and Medicinal Chemistry Letters
AU - Yan, Lin
AU - Hale, Jeffrey J.
AU - Lynch, Christopher
AU - Budhu, Richard
AU - Gentry, Amy
AU - Mills, Sander G.
AU - Hajdu, Richard
AU - Keohane, Carol Ann
AU - Rosenbach, Mark J.
AU - Milligan, James E.
AU - Shei, Gan Ju
AU - Chrebet, Gary
AU - Bergstrom, James
AU - Card, Deborah
AU - ROSEN, H.
AU - Mandala, Suzanne M.
PY - 2004
DA - 2004/10/01
PB - Elsevier
SP - 4861-4866
IS - 19
VL - 14
PMID - 15341940
SN - 0960-894X
SN - 1464-3405
ER -
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BibTex (до 50 авторов)
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@article{2004_Yan,
author = {Lin Yan and Jeffrey J. Hale and Christopher Lynch and Richard Budhu and Amy Gentry and Sander G. Mills and Richard Hajdu and Carol Ann Keohane and Mark J. Rosenbach and James E. Milligan and Gan Ju Shei and Gary Chrebet and James Bergstrom and Deborah Card and H. ROSEN and Suzanne M. Mandala},
title = {Design and synthesis of conformationally constrained 3-(N-alkylamino)propylphosphonic acids as potent agonists of sphingosine-1-phosphate (S1P) receptors},
journal = {Bioorganic and Medicinal Chemistry Letters},
year = {2004},
volume = {14},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/j.bmcl.2004.07.049},
number = {19},
pages = {4861--4866},
doi = {10.1016/j.bmcl.2004.07.049}
}
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MLA
Скопировать
Yan, Lin, et al. “Design and synthesis of conformationally constrained 3-(N-alkylamino)propylphosphonic acids as potent agonists of sphingosine-1-phosphate (S1P) receptors.” Bioorganic and Medicinal Chemistry Letters, vol. 14, no. 19, Oct. 2004, pp. 4861-4866. https://doi.org/10.1016/j.bmcl.2004.07.049.