Compounds that interact with kinases
A method of inhibiting or effecting the activity of protein kinase activity which comprises contacting a protein kinase with a compound of formula (I) being a derivative of a furanose or pyranose form of a monosaccharide, or a pharmaceutically acceptable salt thereof.
1. A compound of formula I
Wherein;
n is 1,
X is selected from: OR1,
R1 and R3 are independently selected from the group consisting of: C1 to C7 alkyl, C1 to C7 alkenyl, C1 to C7 alkynyl, C1 to C7 heteroalkyl, C6 to C14 aryl, C3 to C14 heteroaryl, C6 to C14 arylalkyl and C3 to C14 heteroarylalkyl,
R4 is selected from the group consisting of: H, C1 to C7 alkyl, C1 to C7 alkenyl, C1 to C7 alkynyl, C1 to C7 heteroalkyl, C6 to C14 aryl, C3 to C14 heteroaryl, C6 to C14 arylalkyl and C3 to C14 heteroarylalkyl,
R5 is selected from the group consisting of: H, C1 to C7 alkyl, C1 to C7 alkenyl, C1 to C7 alkynyl, C1 to C7 heteroalkyl, C6 to C14 aryl, C3 to C14 heteroaryl, C6 to C14 arylalkyl or C3 to C14 heteroarylalkyl, C1 to C7 acyl, C6 to C14 arylacyl, and C3 to C14 heteroarylacyl,
R2 is selected from —(C═O)—R3, —(C═O)—OR4, —(C═O)—NH—R4,
Y is selected from the group consisting of:
R6 is selected from the group consisting of H, C1 to C7 alkyl, C1 to C7 alkenyl, C1 to C7 alkynyl, C1 to C7 heteroalkyl, C6 to C14 aryl, C3 to C14 heteroaryl, C6 to C14 arylalkyl and C3 to C14 heteroarylalkyl,
with the proviso that R6, R7 and R8 are not all H,
R9 is selected from H, or —(CO)—R6,
R7, R8, R11, R12, R14, are independently selected from the group consisting of: H, C1 to C7 alkyl, C1 to C7 alkenyl, C1 to C7 alkynyl, C1 to C7 acyl, C1 to C7 heteroalkyl, C6 to C14 aryl, C6 to C14 arylacyl, C6 to C14 heteroaryl, C6 to C14 heteroarylacyl, C6 to C14 arylalkyl or C6 to C14 heteroarylalkyl,
R13 is selected from the group consisting of: unsubstituted phenyl, unsubstituted benzyl, substituted phenyl, substituted benzyl, H, C1 to C7 alkyl, C1 to C7 alkenyl, C1 to C7 alkynyl, C1 to C7 acyl, C1 to C7 heteroalkyl, C6 to C14 aryl, C6 to C14 arylacyl, C6 to C14 heteroaryl, C6 to C14 heteroarylacyl, C6 to C14 arylalkyl or C6 to C14 heteroarylalkyl, —S—R6 or —O—R6,
R15 is absent or is at least one substituent on the aromatic ring which is independently selected from the group consisting of: OH, NO, NO 2 , NH 2 , N 3 , halogen, CF 3 , CHF 2 , CH 2 F, nitrile, alkoxy, aryloxy, amidine, guanidiniums, carboxylic acid, carboxylic acid ester, carboxylic acid amide, aryl, cycloalkyl, heteroalkyl, heteroaryl, aminoalkyl, aminodialkyl, aminotrialkyl, aminoacyl, carbonyl, substituted or unsubstituted imine, sulfate, sulfonamide, phosphate, phosphoramide, hydrazide, hydroxamate, hydroxamic acid, heteroaryloxy, alkyl, aminoaryl, aminoheteroaryl, thioalkyl, thioaryl or thioheteroaryl.
2. The compound of claim 1 , wherein R7 and R8 combine to form a cyclic structure.
3. The compound of claim 1 , wherein R6 and one of R7 or R8 combine to form a cyclic structure.
4. The compound of claim 1 , wherein R11 and R12 combine to form a cyclic structure.
5. The compound of claim 1 , wherein the groups R1 , R2, R3, R4 and R5 are cycle, acyclic branched, or linear.
6. The compound of claim 1 , wherein R2 and R3 combine to form a ring structure.
7. The compound of claim 1 , wherein the groups R4 and R5 combine to form a ring structure.
8. A compound of claim 1 in which at least one of R1 to R14 is substituted with a substituent selected from the group, OH, NO, NO 2 , NH 2 , N 3 , halogen, CF 3 , CHF 2 , CH 2 F, nitrile, alkoxy, aryloxy, amidine, guanidiniums, carboxylic acid, carboxylic acid ester, carboxylic acid amide, aryl, cycloalkyl, heteroalkyl, heteroaryl, aminoalkyl, aminodialkyl, aminotrialkyl, aminoacyl, carbonyl, substituted or unsubstituted imine, sulfate, sulfonamide, phosphate, phosphoramide, hydrazide, hydroxamate, hydroxamic acid, heteroaryloxy, aminoalkyl, alkyl, aminoheteroaryl, thioalkyl, thioaryl or thioheteroaryl.
9. The compound of claim 1 in which the group X is
10. The compound of claim 1 in which the group X is
11. The compound of claim 1 in which the group X is —OR1.
12. The compound of claim 9 wherein Y is
13. The compound of claim 10 wherein Y is
14. The compound of claim 9 , wherein Y is
15. The compound of claim 10 , wherein Y is
16. The compound of claim 9 , wherein Y is
17. The compound of claim 10 , wherein Y is
18. The compound claim 9 , wherein Y is
19. The compound claim 10 , wherein Y is
20. The compound of claim 9 , wherein Y is
21. The compound of claim 10 , wherein Y is
22. The compound of claim 9 , wherein Y is
23. The compound of claim 10 , wherein Y is
24. The compound claim 9 , wherein Y is
25. The compound claim 10 , wherein Y is