3-fluoro- and 3,3-difluoro-3,4-dideoxy-KRN7000 analogues as new potent immunostimulator agents: Total synthesis and biological evaluation in human invariant natural killer t cells and mice

Journal of Medicinal Chemistry

Volumn 55, Issue 3, 2012, Pages 1227-1241

  Hunault, Julie ^a   Diswall, Mette ^b   Frison, Jean Cédric ^a   Blot, Virginie ^a   Rocher, Jézabel ^b   Marionneau Lambot, Séverine ^c   Oullier, Thibauld ^c   Douillard, Jean Yves ^d   Guillarme, Stéphane ^e   Saluzzo, Christine ^e   Dujardin, Gilles ^e   Jacquemin, Denis ^a   Graton, Jérôme ^a   Le Questel, Jean Yves ^a   Evain, Michel ^a   Lebreton, Jacques ^a   Dubreuil, Didier ^a   Le Pendu, Jacques ^b   Pipelier, Muriel ^a  

^a UNIVERSITÉ DE NANTES   (France)

^b INSERM   (France)

^c Plateforme in Vivo du Cancéropôle Grand Ouest ^*  (France)

^d CENTRE RENÉ GAUDUCHEAU   (France)

^e UNIVERSITÉ DU MAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 O (ALPHA DEXTRO GALACTOPYRANOSYL) 2 HEXACOSANOYLAMINO 3,3 DI FLUORO HEPTADECANE; 1 O (ALPHA GALACTOPYRANOSYL) 2 HEXACOSANOYLAMINO 1,3,4 OCTADECANETRIOL; 2 (HEXACOSANOYLAMINO) 3,3 DIFLUORO 1 O (2,3,4,6 TETRA O BENZYL ALPHA GALACTOPYRANOSYL)OCTADEC 5 ENE; 2 (TERT BUTYLOXYCARBONYLAMINO) 3 FLUORO 1 (2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL)HEPTADEC 4 ENE; 2 HEXACOSANOYLAMINO 1 (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GALACTOPYRANOSYL)HEPTADECANE; 2 HEXACOSANOYLAMINO 1 (ALPHA DEXTRO GALACTOPYRANOSYL)HEPTADECANE; 2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GALACTOPYRANOSYLMETHYL) 5 VINYL 1,3 OXAZOLIDIN (3H) 2 ONE; 3 FLUORO 2 (HEXACOSANOYLAMINO) 1 (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GALACTOPYRANOSYL)HEPTADECANE; 3 FLUORO 2 (HEXACOSANOYLAMINO) 1 (2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL)HEPTADEC 4 ENE; 3 FLUORO 2 HEXACOSANOYLAMINO 1 (ALPHA DEXTRO GALACTOPYRANOSYL)HEPTADECANE; 3,4 DIDEOXY 3 FLUORO KRN7000; 3,4 DIDEOXY 3,3 DIFLUORO KRN7000; 4 (TERT BUTYLOXYCARBONYLAMINO) 3 FLUORO 5 (2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL)PENT 1 ENE; 5 (HEXACOSANOYLAMINO) 4,4 DIFLUORO 6 O (2,3,4,6 TETRA O BENZYL ALPHA GALACTOPYRANOSYL)HEX 1 ENE; 5 (TERT BUTOXYCARBONYLAMINO) 4 FLUORO HEX 1,3 DIEN 6 OL; 5 (TERT BUTOXYCARBONYLAMINO) 4,4 DIFLUORO HEX 1 EN 6 OL; 5 (TERT BUTYLOXYCARBONYLAMINO) 4,4 DIFLUORO 6 O (2,3,4,6 TETRA O BENZYL ALPHA GALACTOPYRANOSYL)HEX 1 ENE; ALPHA GALACTOSYLCERAMIDE; CD1D ANTIGEN; ETHYL 2 (TERT BUTOXYCARBONYLAMINO) 3,3 DIFLUORO HEX 6 ENOATE; GAMMA INTERFERON; IMMUNOSTIMULATING AGENT; INTERLEUKIN 13; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CROSS COUPLING REACTION; DEACETYLATION; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE ACTIVATED CELL SORTING; FLUORINE NUCLEAR MAGNETIC RESONANCE; HELA CELL; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NATURAL KILLER CELL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; T LYMPHOCYTE ACTIVATION; TH1 TH2 BALANCE;

ADJUVANTS, IMMUNOLOGIC; ANIMALS; ANTIGEN-PRESENTING CELLS; ANTIGENS, CD1D; CELL LINE; FEMALE; GALACTOSYLCERAMIDES; HUMANS; HYDROGEN BONDING; MICE; MICE, INBRED C57BL; MODELS, MOLECULAR; NATURAL KILLER T-CELLS; PROTEIN STABILITY; RECEPTORS, ANTIGEN, T-CELL; SPECIES SPECIFICITY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TH1 CELLS; TH2 CELLS;

EID: 84856935249     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201368m     Document Type: Article

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