6″-amino-6″-deoxygalactosylceramides

1. A compound of Formula (I):

wherein,

R 1 is:

(i) hydrogen; or

(ii) —SO 2 R 10 ,

wherein R 10 is:

halo; hydroxy; OR 11 ; OR 12 ; amino; NHR 11 ; N(R 11 ) 2 ; NHR 12 ; N(R 12 ) 2 ;

aralkylamino; or

C 1 -C 12 alkyl optionally substituted with halo, hydroxy, oxo, nitro, OR 11 , OR 12 , acyloxy, amino, NHR 11 ; N(R 11 ) 2 ; NHR 12 ; N(R 12 ) 2 , aralkylamino, mercapto, thioalkoxy, S(O)R 11 , S(O)R 12 , SO 2 R 11 , SO 2 R 12 , NHSO 2 R 11 , NHSO 2 R 12 , sulfate, phosphate, cyano, carboxyl, C(O)R 11 , C(O)R 12 , C(O)OR 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C 3 -C 10 cycloalky containing 0-3 R 13 , C 3 -C 10 heterocyclyl containing 0-3 R 13 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 5 -C 10 cycloalkenyl, C 5 -C 10 heterocycloalkenyl, C 6 -C 20 aryl containing 0-3R 14 , or heteroaryl containing 0-3 R 14 ; or

C 3 -C 10 cycloalkyl, C 3 -C 10 heterocyclyl, C 5 -C 10 cycloalkenyl, or C 5 -C 10 heterocycloalkenyl optionally substituted with one or more halo, hydroxy, oxo, OR 11 , OR 12 , acyloxy, nitro, amino, NHR 11 , N(R 11 ) 2 , NHR 12 , N(R 12 ) 2 , aralkylamino, mercapto, thioalkoxy, S(O)R 11 , S(O)R 12 , SO 2 R 11 , SO 2 R 12 , NHSO 2 R 11 , NHSO 2 R 12 , sulfate, phosphate, cyano, carboxyl, C(O)R 11 , C(O)R 12 , C(O)OR 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , alkyl, haloalkyl, C 3 -C 10 cycloalkyl containing 0-3 R 13 , C 3 -C 10 heterocyclyl containing 0-3 R 13 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 5 -C 10 cycloalkenyl, C 5 -C 10 heterocycloalkenyl, C 6 -C 20 aryl heteroaryl containing 0-3 R 14 , or C 6 -C 20 heteroaryl containing 0-3 R 14 ; or

C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, aryl, or heteroaryl optionally substituted with one or more halo, hydroxy, OR 11 , OR 12 , acyloxy, nitro, amino, NHR 11 , N(R 11 ) 2 , NHR 12 , N(R 12 ) 2 , aralkylamino, mercapto, thioalkoxy, S(O)R 11 , S(O)R 12 , SO 2 R 11 , SO 2 R 12 , NHSO 2 R 11 , NHSO 2 R 12 , sulfate, phosphate, cyano, carboxyl, C(O)R 11 , C(O)R 12 , C(O)OR 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , alkyl, haloalkyl, C 3 -C 10 cycloalkyl containing 0-3 R 13 , C 3 -C 10 heterocyclyl containing 0-3 R 13 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 5 -C 10 cycloalkenyl, C 5 -C 10 heterocycloalkenyl, C 6 -C 20 aryl containing 0-3 R 14 , or C 6 -C 20 heteroaryl containing 0-3 R 14 ; or

(iii) —C(O)R 10 , wherein R 10 is defined as above; or

(iv) —C(R 10 ) 2 (R 15 ), wherein R 10 is defined as above; R 15 is hydrogen, R 10 , or R 15 and R 2 when taken together form a double bond between the carbon to which R 15 is attached and the nitrogen to which R 2 is attached; or

(v) R 1 and R 2 form a heterocyclyl of 3-10 ring atoms optionally substituted with R 10 ;

R 2 is hydrogen, or R 2 and R 15 when taken together form a double bond between the carbon to which R 15 is attached and the nitrogen to which R 2 is attached, or R 2 and R 1 form a heterocyclyl of 3-10 ring atoms optionally substituted with R 10 ;

R 3 , R 4 , R 5 , R 6 and R 7 are each independently hydrogen, C 1 -C 6 alkyl, C 6 -C 12 aralkyl, or C 1 -C 6 acyl;

R 8 is —(CH 2 ) x CH 3 ;

R 9 is a linear or branched C 3 -C 100 alkyl;

R 11 is C 1 -C 20 alkyl optionally substituted with halo, hydroxy, alkoxy, amino, alkylamino, dialkylamino, sulfate, or phosphate;

R 12 is aryl optionally substituted with halo, haloalkyl, hydroxy, alkoxy, nitro, amino, alkylamino, dialkylamino, sulfate, or phosphate;

Each R 13 is independently halo, haloalkyl, hydroxy, alkoxy, oxo, amino, alkylamino, dialkylamino, sulfate, or phosphate;

Each R 14 is independently halo, haloalkyl, hydroxy, alkoxy, nitro, amino, alkylamino, dialkylamino, sulfate, or phosphate; and

x is 1-100.

2. The compound of claim 1 wherein x is 24 and R 9 is n-tetradecyl.

3. The compound of claim 2 wherein R 1 is SO 2 R 10 .

4. The compound of claim 3 wherein R 10 is aryl substituted with N(R 11 ) 2 .

5. The compound of claim 2 wherein R 1 is C(O)R 10 .

6. The compound of claim 5 wherein R 10 is C 1 -C 6 alkyl substituted with halo, hydroxy, oxo, nitro, OR 11 , OR 12 , acyloxy, amino, NHR 11 , N(R 11 ) 2 , NHR 12 , N(R 12 ) 2 , aralkylamino, mercapto, thioalkoxy, S(O)R 11 , S(O)R 12 , SO 2 R 11 , SO 2 R 12 , NHSO 2 R 11 , NHSO 2 R 12 , sulfate, phosphate, cyano, carboxyl, C(O)R 11 , C(O)R 12 , C(O)OR 11 , C(O)NH 2 , C(O)NHR 11 , C(O)N(R 11 ) 2 , C 3 -C 10 cycloalkyl containing 0-3 R 13 , C 3 -C 10 heterocyclyl containing 0-3 R 13 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 5 -C 10 cycloalkenyl, C 5 -C 10 heterocycloalkenyl, C 6 -C 20 aryl containing 0-3 R 14 , or C 6 -C 20 heteroaryl containing 0-3 R 14 .

7. The compound of claim 6 wherein R 10 is C 1 -C 6 alkyl substituted with NHSO 2 R 12 .

8. The compound of claim 6 , wherein R 10 is alkyl substituted with C(O)R 12 .

9. The compound of claim 6 wherein R 10 is alkyl is substituted with C 5 -C 10 heterocyclyl containing 0-3 R 13 .

10. A probe for observing glycolipid association with CD1d and NKT cell receptors during NKT cell stimulation comprising a formula of Formula (II):

wherein:

X is —SO 2 —, —C(O)—, or absent;

Y is a linker group; and

Z is a reporter group.

11. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.