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  • Stereochemistry-activity relationship of orally active tetralin S1P agonist prodrugs.

Stereochemistry-activity relationship of orally active tetralin S1P agonist prodrugs.

Bioorganic & medicinal chemistry letters (2010-03-02)
Bin Ma, Kevin M Guckian, Edward Yin-Shiang Lin, Wen-Cherng Lee, Daniel Scott, Gnanasambandam Kumaravel, Timothy L Macdonald, Kevin R Lynch, Cheryl Black, Sowmya Chollate, Kyungmin Hahm, Gregg Hetu, Ping Jin, Yi Luo, Ellen Rohde, Anthony Rossomando, Robert Scannevin, Joy Wang, Chunhua Yang
ABSTRACT

Modifying FTY720, an immunosuppressant modulator, led to a new series of well phosphorylated tetralin analogs as potent S1P1 receptor agonists. The stereochemistry effect of tetralin ring was probed, and (-)-(R)-2-amino-2-((S)-6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)propan-1-ol was identified as a good SphK2 substrate and potent S1P1 agonist with good oral bioavailability.

MATERIALS
Product Number
Brand
Product Description

Supelco
1,2,3,4-Tetrahydronaphthalene, analytical standard
Sigma-Aldrich
1,2,3,4-Tetrahydronaphthalene, anhydrous, 99%
Sigma-Aldrich
1,2,3,4-Tetrahydronaphthalene, ReagentPlus®, 99%
Sigma-Aldrich
1,2,3,4-Tetrahydronaphthalene, reagent grade, ≥97%