1,2,3-Triazolyl purine derivatives

1. A compound having Formula I,

wherein:

R 1 represents an alkyl, an aryl, —SiR 4 , —SnR 5 , —B(R 4 ) 2 , —B(OH) 2 , an amide, an imide, or an organometallic;

R 2 and R 3 independently represent N, CH, or CR 6 ;

R 4 independently represents —R 5 or —OR 5 ;

R 5 , R 7 and R 8 , independently of each other and independently at each position, represent alkyl, cycloalkyl, or aryl;

R 7 and R 8 independently, may be combined to represent a heterocyclic alkyl or a heterocyclic aryl;

R 6 independently represents an alkyl or an aryl;

Y represents H, an alkyl, an aryl, or a saccharide moiety;

alkyl groups are branched or unbranched, saturated or unsaturated, and have 1-18 carbon atoms in their longest chain;

cycloalkyl groups are carbocyclic or heterocyclic, fused or unfused, non-aromatic ring systems having a total of 5-16 ring members including substituent rings;

aryl groups are carbocyclic or heterocyclic;

carbocyclic aryl groups are fused or unfused ring systems having a total of 6-16 ring members including substituent rings;

heterocyclic aryl groups are fused or unfused ring systems having a total of 5-16 ring members including substituent rings;

halo substituents are fluoro, chloro, bromo, or iodo;

each alkyl, cycloalkyl, and aryl, independently, may be unsubstituted or substituted with one or more substituent at any position;

alkyl substituents are halo, hydroxyl, —OR 5 , —SR 5 , —S(O)R 4 , —S(O) 2 R 4 , —NH 2 , —NHR 5 , —NR 7 R 8 , cycloalkyl, or aryl;

cycloalkyl substituents are halo, hydroxyl, —OR 5 , —SR 5 , —NH 2 , —NHR 5 , —NR 7 R 8 , alkyl, cycloalkyl, or aryl;

aryl substituents are halo, hydroxyl, —OR 5 , —SR 5 , —NH 2 , —NHR 5 , —NR 7 R 8 , —CN, alkyl, cycloalkyl, aryl, nitro, or carboxyl; and

heterocyclic alkyl and heterocyclic aryl have at least one heteroatom selected from the group consisting of oxygen, nitrogen and sulfur.

2. A compound according to claim 1 , wherein Y represents a saccharide moiety, and the saccharide moiety has the following structure:

wherein:

Y 1 represents C, N, or O;

R 20 and R 21 independently represent H, —OR 23 , —NR 7 R 8 , R 6 , or halo;

R 22 represents H, OH, —CH 2 OR 6 , —CH 2 OR 23 , —NR 7 R 8 , —CH 2 NR 7 R 8 , R 6 ; and

R 23 represents H or a protecting group.

3. A compound according to claim 2 , wherein Y 1 represents O.

4. A compound according to claim 2 , wherein R 22 represents —CH 2 O(alkyl) or

—CH 2 OR 23 .

5. A compound according to claim 1 , wherein the saccharide moiety is selected from the group consisting of 1-ribosyl and 2′-deoxy-1-ribosyl.

6. A compound according to claim 1 , wherein R 1 is an imide and the imide is represented by:

wherein:

R 24 and R 25 are independently an alkyl or an aryl; and

R 24 and R 25 independently, may be combined to represent a succinimidyl group that may be fused or unfused, and substituted or unsubstituted.

7. A compound according to claim 6 , wherein R 1 is phthalimidyl.

8. A compound according to claim 1 , wherein R 1 is an amide and the amide is represented by:

wherein:

R 26 and R 27 are independently an alkyl or an aryl.

9. A compound according to claim 1 , wherein R 1 is an organometallic and the organometallic has a complex of Fe, Mo, Ru, or Pt.

10. A compound according to claim 9 , wherein R 1 is ferrocenyl.

11. A compound according to claim 1 , wherein Y represents a saccharide moiety selected from the group consisting of 1-ribosyl and 2′-deoxy-1-ribosyl; R 2 is N; R 3 is CH; and R 1 represents:

12. A compound having Formula II,

wherein:

R 1 represents an alkyl, an aryl, —SiR 4 , —SnR 5 , —B(R 4 ) 2 , —B(OH) 2 , an amide, an imide, or an organometallic;

R 2 and R 3 independently represent N, CH, or CR 6 ;

X represents —OR 9 , —SR 9 , or —NR 9 R 10 ;

Y represents H, an alkyl, an aryl, or a saccharide moiety;

R 4 independently represents —R 5 or —OR 5 ;

R 5 , R 7 and R 8 , independently of each other and independently at each position, represent alkyl, cycloalkyl, or aryl; and

R 6 independently represents an alkyl or an aryl;

R 9 and R 10 independently represent H, an alkyl, or an aryl;

R 7 and R 8 , R 9 and R 10 independently, may be combined to represent a heterocyclic alkyl or a heterocyclic aryl;

alkyl groups are branched or unbranched, saturated or unsaturated, and have 1-18 carbon atoms in their longest chain;

cycloalkyl groups are carbocyclic or heterocyclic, fused or unfused, non-aromatic ring systems having a total of 5-16 ring members including substituent rings;

aryl groups are carbocyclic or heterocyclic;

carbocyclic aryl groups are fused or unfused ring systems having a total of 6-16 ring members including substituent rings;

heterocyclic aryl groups are fused or unfused ring systems having a total of 5-16 ring members including substituent rings;

halo substituents are fluoro, chloro, bromo, or iodo;

each alkyl, cycloalkyl, and aryl, independently, may be unsubstituted or substituted with one or more substituent at any position;

alkyl substituents are halo, hydroxyl, —OR 5 , —SR 5 , —S(O)R 4 , —S(O) 2 R 4 , —NH 2 , —NHR 5 , —NR 7 R 8 , cycloalkyl, or aryl;

cycloalkyl substituents are halo, hydroxyl, —OR 5 , —SR 5 , —NH 2 , —NHR 5 , —NR 7 R 8 , alkyl, cycloalkyl, or aryl;

aryl substituents are halo, hydroxyl, —OR 5 , —SR 5 , —NH 2 , —NHR 5 , —NR 7 R 8 , —CN, alkyl, cycloalkyl, aryl, nitro, or carboxyl; and

heterocyclic alkyl and heterocyclic aryl have at least one heteroatom selected from the group consisting of oxygen, nitrogen and sulfur.

13. A compound according to claim 12 , wherein X is —NR 9 R 10 and R 1 represents —SiR 4 , —SnR 5 , —B(R 4 ) 2 , —B(OH) 2 , an imide, or an organometallic.

14. A compound according to claim 12 , wherein X is —NR 9 R 10 and R 9 and R 10 independently represent an alkyl or an aryl.

15. A compound according to claim 12 , wherein R 2 is N and R 3 is CH.

16. A compound according to claim 12 , wherein R 1 is phenyl.

17. A compound according to claim 12 , wherein R 9 and R 10 independently represent H or CH 2 Ph; or R 9 and R 10 are combined to represent CH 2 CH 2 OCH 2 CH 2 .

18. A compound according to claim 12 , wherein R 1 is an imide and the imide is represented by:

wherein:

R 24 and R 25 are independently an alkyl or an aryl; and

R 24 and R 25 independently, may be combined to represent a succinimidyl group that may be fused or unfused, and substituted or unsubstituted.

19. A compound according to claim 18 , wherein R 1 is phthalimidyl.

20. A compound according to claim 12 , wherein R 1 is an amide and the amide is represented by:

wherein:

R 26 and R 27 are independently an alkyl or an aryl.

21. A compound according to claim 12 , wherein R 1 is an organometallic and the organometallic has a complex of Fe, Mo, Ru, or Pt.

22. A compound according to claim 21 , wherein R 1 is ferrocenyl.

23. A compound according to claim 12 , wherein Y represents a saccharide moiety, and the saccharide moiety has the following structure:

wherein:

Y 1 represents C, N, or O;

R 20 and R 21 independently represent H, —OR 23 , —NR 7 R 8 , R 6 , or halo;

R 22 represents H, OH, —CH 2 OR 6 , —CH 2 OR 23 , —NR 7 R 8 , —CH 2 NR 7 R 8 , R 6 ; and

R 23 represents H or a protecting group.

24. A compound according to claim 23 , wherein Y 1 represents O.

25. A compound according to claim 23 , wherein R 22 represents —CH 2 O(alkyl) or

—CH 2 OR 23 .

26. A compound according to claim 12 , wherein the saccharide moiety is selected from the group consisting of 1-ribosyl and 2′-deoxy-1-ribosyl.

27. A compound having Formula III,

wherein:

R 9 , R 10 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 independently represent N or CR 11 ;

R 11 independently represents —R 18 , —OR 19 , —SR 19 , —N(R 18 ) 2 , R 18 C(O)—, nitro, or halo;

R 18 independently represents H, an alkyl group, or an aryl;

R 19 independently represents R 18 or a protecting group;

Y represents R 18 or a saccharide moiety;

alkyl groups are branched or unbranched, saturated or unsaturated, and have 1-18 carbon atoms in their longest chain;

cycloalkyl groups are carbocyclic or heterocyclic, fused or unfused, non-aromatic ring systems having a total of 5-16 ring members including substituent rings;

aryl groups are carbocyclic or heterocyclic;

carbocyclic aryl groups are fused or unfused ring systems having a total of 6-16 ring members including substituent rings;

heterocyclic aryl groups are fused or unfused ring systems having a total of 5-16 ring members including substituent rings;

halo substituents are fluoro, chloro, bromo, or iodo;

each alkyl, cycloalkyl, and aryl, independently, may be unsubstituted or substituted with one or more substituent at any position;

alkyl substituents are halo, hydroxyl, —OR 5 , —SR 5 , —S(O)R 4 , —S(O) 2 R 4 , —NH 2 , —NHR 5 , —NR 7 R 8 , cycloalkyl, or aryl;

cycloalkyl substituents are halo, hydroxyl, —OR 5 , —SR 5 , —NH 2 , —NHR 5 , —NR 7 R 8 , alkyl, cycloalkyl, or aryl;

aryl substituents are halo, hydroxyl, —OR 5 , —SR 5 , —NH 2 , —NHR 5 , —NR 7 R 8 , —CN, alkyl, cycloalkyl, aryl, nitro, or carboxyl; and

heterocyclic alkyl and heterocyclic aryl have at least one heteroatom selected from the group consisting of oxygen, nitrogen and sulfur;

R 4 independently represents —R 5 or —OR 5 ;

R 5 , R 7 and R 8 , independently of each other and independently at each position, represent alkyl, cycloalkyl, or aryl; and

R 7 and R 8 independently, may be combined to represent a heterocyclic alkyl or a heterocyclic aryl.

28. A compound according to claim 27 , wherein Y represents a saccharide moiety, and the saccharide moiety has the following structure:

wherein:

Y 1 represents C, N, or O;

R 20 and R 21 independently represent H, —OR 23 , —NR 7 R 8 , R 6 , or halo;

R 22 represents H, OH, —CH 2 OR 6 , —CH 2 OR 23 , —NR 7 R 8 , —CH 2 NR 7 R 8 , R 6 ;

R 23 represents H or a protecting group; and

R 6 represents an alkyl or an aryl.

29. A compound according to claim 28 , wherein Y 1 represents O.

30. A compound according to claim 28 , wherein R 22 represents —CH 2 O(alkyl) or

—CH 2 OR 23 .

31. A compound according to claim 27 , wherein the saccharide moiety is selected from the group consisting of 1-ribosyl and 2′-deoxy-1-ribosyl.

32. A compound according to claim 27 , wherein no more than one of R 14 , R 15 , R 16 , and R 17 represent N.

33. A compound according to claim 27 , wherein R 9 , R 14 , R 15 , R 16 , and R 17 are CH; and R 10 , R 12 , and R 13 are N.

34. A compound according to claim 27 , wherein R 9 , R 14 , R 15 , and R 16 are CH; R 10 , R 12 , and R 13 are N; and R 17 is N or CH.

35. A method of treating cancer, comprising administering to a patient in need thereof an effective amount of a compound of Formula I or a compound below: