Synthesis of (S)-FTY720 vinylphosphonate analogues and evaluation of their potential as sphingosine kinase 1 inhibitors and activators

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 9, 2013, Pages 2503-2510

  Liu, Zheng ^a   Macritchie, Neil ^b   Pyne, Susan ^b   Pyne, Nigel J ^b   Bittman, Robert ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Allosterism; B alkyl Suzuki cross coupling; Epoxide opening; FTY720; Sphingosine 1 phosphate

Indexed keywords

1 OCTYL 4 VINYLBENZENE; 2 (4 OCTYLPHENETHYL)OXIRANE 2 CARBALDEHYDE; 2 METHYLENE 4 (4 OCTYLPHENYL)BUTAN 1 OL; 3 AMINO 3 (FLUOROMETHYL) 5 (4 OCTYLPHENYL)PENT 1 ENYLPHOSPHONIC ACID; 3 AZIDO 3 (FLUOROMETHYL) 5 (4 OCTYLPHENYL)PENT 1 ENYLPHOSPHONIC ACID; 3 AZIDO 3 (HYDROXYMETHYL) 5 (4 OCTYLPHENYL)PENT 1 ENYLPHOSPHONIC ACID; 4 AMINO 4 (HYDROXYMETHYL) 6 (4 OCTYLPHENYL)HEX 2 ENOIC ACID; 5 (4 OCTYLPHENETHYL) 5 AMINO TETRAHYDROPYRAN 2 ONE; 5 (4 OCTYLPHENETHYL) 5 AZIDO 5,6 DIHYDROPYRAN 2 ONE; DIMETHYL 2 [ 2 (4 OCTYLPHENETHYL)OXIRAN 2 YL]VINYLPHOSPHONATE; DIMETHYL 3 (AZIDOMETHYL) 3 HYDROXY 5 (4 OCTYLPHENYL)PENT 1 ENYLPHOSPHONATE; DIMETHYL 3 AMINO 3 (FLUOROMETHYL) 5 (4 OCTYLPHENYL)PENT 1 ENYLPHOSPHONATE; DIMETHYL 3 AMINO 3 (HYDROXYMETHYL) 5 (4 OCTYLPHENYL)PENT 1 ENYLPHOSPHONATE; DIMETHYL 3 AZIDO 3 (FLUOROMETHYL) 5 (4 OCTYLPHENYL)PENT 1 ENYLPHOSPHONATE; DIMETHYL 3 AZIDO 3 (HYDROXYMETHYL) 5 (4 OCTYLPHENYL)PENT 1 ENYLPHOSPHONATE; ENZYME ACTIVATOR; ENZYME INHIBITOR; ETHYL 3 [2 (4 OCTYLPHENETHYL)OXIRAN 2 YL]ACRYLATE; ETHYL 4 (AZIDOMETHYL) 4 HYDROXY 6 (4 OCTYLPHENYL)HEX 2 ENOATE; ETHYL 4 AMINO 4 (HYDROXYMETHYL) 6 (4 OCTYLPHENYL)HEX 2 ENOATE; ETHYL 4 AZIDO 4 (HYDROXYMETHYL) 6 (4 OCTYLPHENYL)HEX 2 ENOATE; FINGOLIMOD; PHOSPHONIC ACID DERIVATIVE; SPHINGOSINE KINASE 1; UNCLASSIFIED DRUG; VINYLPHOSPHONIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DRUG SYNTHESIS; HORNER WADSWORTH EMMONS REACTION; HUMAN; HUMAN CELL; HYDROGENATION; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; SUZUKI REACTION; TEMPERATURE;

CELLS, CULTURED; DOSE-RESPONSE RELATIONSHIP, DRUG; HEK293 CELLS; HUMANS; MOLECULAR STRUCTURE; ORGANOPHOSPHONATES; PHOSPHOTRANSFERASES (ALCOHOL GROUP ACCEPTOR); PROTEIN KINASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84876123091     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.02.042     Document Type: Article

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