A photoreactive analogue of the immunosuppressant FTY720.
An azido group was incorporated into the immunomodulatory agent FTY720, accomplishing the first synthesis of a photoactivatable analogue of this ligand (2) in 9 steps from 2-(4-hydroxyphenyl)ethanol and in 34% overall yield. The key steps are formation of a primary amine at a quaternary center of aniline derivative 13 followed by selective diazotization of the arylamine.
Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.
Chaode
C
Sun
Robert
R
Bittman
D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry*; D000068876:Fingolimod Hydrochloride; D007166:Immunosuppressive Agents / Q000138:chemical synthesis / Q000737:chemistry*; D010777:Photochemistry; D011412:Propanolamines / Q000138:chemical synthesis / Q000737:chemistry*; D011409:Propylene Glycols / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000737:chemistry
C516082:2-(3-azido-4-octylphenethyl)-2-aminopropane-1,3-diol; D001386:Azides; D007166:Immunosuppressive Agents; D011412:Propanolamines; D011409:Propylene Glycols; D000068876:Fingolimod Hydrochloride; D013110:Sphingosine