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Design and synthesis of conformationally constrained 3-(N-alkylamino)propylphosphonic acids as potent agonists of sphingosine-1-phosphate (S1P) receptors

Yan, Lin ; Hale, Jeffrey J ; Lynch, Christopher L ; Budhu, Richard ; Gentry, Amy ; Mills, Sander G ; Hajdu, Richard ; Keohane, Carol Ann ; Rosenbach, Mark J ; Milligan, James A ; Shei, Gan-Ju ; Chrebet, Gary ; Bergstrom, James ; Card, Deborah ; Rosen, Hugh ; Mandala, Suzanne M

Bioorganic & medicinal chemistry letters, 04 October 2004, Vol.14(19), pp.4861-6 [Peer Reviewed Journal]

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Title:
Design and synthesis of conformationally constrained 3-(N-alkylamino)propylphosphonic acids as potent agonists of sphingosine-1-phosphate (S1P) receptors
Author: Yan, Lin ; Hale, Jeffrey J ; Lynch, Christopher L ; Budhu, Richard ; Gentry, Amy ; Mills, Sander G ; Hajdu, Richard ; Keohane, Carol Ann ; Rosenbach, Mark J ; Milligan, James A ; Shei, Gan-Ju ; Chrebet, Gary ; Bergstrom, James ; Card, Deborah ; Rosen, Hugh ; Mandala, Suzanne M
Description: 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.
Is Part Of: Bioorganic & medicinal chemistry letters, 04 October 2004, Vol.14(19), pp.4861-6
Identifier: ISSN: 0960-894X ; PMID: 15341940 Version:1
Subjects: Drug Design ; Organophosphonates -- Chemical Synthesis ; Receptors, Lysosphingolipid -- Agonists
Language: English
Source: MEDLINE/PubMed (U.S. National Library of Medicine)

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