Compounds having antiparasitic or anti-infectious activity

1. A compound of formula I:

or formula II:

or a pharmaceutically acceptable salt of formula I or formula II, wherein:

R 1 is H, hydroxyl, alkoxy, acyl, alkyl, cycloalkyl, aryl, or heteroaryl;

R 2 is methyl, haloalkyl, or heteroaryl;

R 4 is carbonyloxy or carbonyldioxy;

R 3 is a diaryl ether; and

R 5 and R 7 are each individually H, halogen, alkoxy, alkyl, haloalkyl, aryl, nitro, cyano, amino, amido, acyl, carboxyl, substituted carboxyl, or —SO 2 R 10 , wherein R 10 is H, alkyl, amino or haloalkyl;

R 6 is H, halogen, alkoxy, alkyl, haloalkyl, aryl, cyano, amino, amido, acyl, carboxyl, substituted carboxyl, or —SO 2 R 10 , wherein R 10 is H, alkyl, amino or haloalkyl; and

R 8 is H, halogen, alkoxy, haloalkyl, aryl, nitro, cyano, amino, amido, acyl, carboxyl, substituted carboxyl, or —SO 2 R 10 , wherein R 10 is H, alkyl, amino or haloalkyl;

provided that in formula I, R 6 is not H or methoxy; and in formula II that if R 4 is carbonyldioxy then R 7 is not methoxy.

2. The compound of claim 1 , wherein R 5 and R 7 of formula I or II are each halogen or haloalkyl.

3. The compound of claim 1 , wherein R 5 and R 7 of formula I or II are each F.

4. The compound of claim 1 , wherein R 4 is carbonyloxy or carbonyldioxy.

5. The compound of claim 1 , wherein R 7 of formula I or II is not methoxy.

6. The compound of claim 1 , wherein R 6 of formula I or II is halogen and R 5 and R 7 are each H.

7. The compound of claim 1 , wherein R 2 of formula I or II is methyl.

8. The compound of claim 1 , wherein R 1 is H, alkyl, or cycloalkyl.

9. The compound of claim 1 , wherein the compound of formula II has a structure represented by formula III:

wherein R 9 is alkyl, alkenyl, alkyl amino, amido, aminocarbonyl, hydroxyalkyl, alkoxyalkyl or alkyl ether.

10. The compound of claim 1 , wherein the compound of formula II has a structure represented by formula IV:

wherein R 9 is alkyl, alkenyl, alkyl amino, amido, aminocarbonyl, hydroxyalkyl, alkoxyalkyl or alkyl ether.

11. The compound of claim 1 , wherein the compound is a compound of formula I.

12. The compound of claim 1 , wherein R 7 is methoxy.

13. The compound of claim 1 , wherein R 6 is halogen.

14. The compound of claim 1 , wherein R 3 is

wherein R 13 and R 14 are each individually selected from at least one of alkoxy, halogen-substituted alkoxy, halogenated lower alkyl, alkyl, methylsulfonyl, or halogen; c is 0 to 5; and d is 0 to 5.

15. The compound of claim 1 , wherein R 1 is H; R 2 is methyl; R 6 is halogen; R 7 is H or methoxy; and R 5 and R 8 are each H.

16. A compound of formula XI:

or a pharmaceutically acceptable salt of formula XI, wherein:

R 1 is H;

R 2 is methyl;

R 3 is an optionally substituted diaryl ether

R 6 is halogen;

R 7 is H or methoxy; and

R 5 and R 8 are each H.

17. The compound of claim 16 , wherein R 3 is

wherein R 13 and R 14 are each individually selected from at least one of alkoxy, halogen-substituted alkoxy, halogenated lower alkyl, alkyl, methylsulfonyl, or halogen; c is 0 to 5; and d is 0 to 5.

18. A compound, or a pharmaceutically acceptable salt thereof, having a structure of:

19. A compound, or a pharmaceutically acceptable salt thereof, having a structure of:

20. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, having a structure of:

21. A composition comprising a pharmacologically active amount of at least one compound of claim 1 or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier.

22. A composition comprising a pharmacologically active amount of at least one compound of claim 18 or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier.

23. The composition according to claim 21 , further comprising at least one further antimalarial agent.

24. The composition according to claim 23 , wherein the further antimalarial agent is selected from quinine, chloroquine, atovaquone, proguanil, primaquine, amodiaquine, mefloquine, piperaquine, artemisinin, methylene blue, pyrimethamine, sulfadoxine, artemether-lumefantrine, dapsone-chlorproguanil, artesunate, quinidine, clopidol, pyridine/pyridinol analogs, 4(1H)-quinolone analogs, dihydroartemisinin, a mixture of atovaquone and proguanil, an endoperoxide, an acridone, a pharmachin or any combination of these.

25. The composition according to claim 22 , further comprising at least one further antimalarial agent.

26. A compound of formula XI:

or a pharmaceutically acceptable salt of formula XI, wherein:

R 1 is H, hydroxyl, alkoxy, acyl, alkyl, cycloalkyl, aryl, or heteroaryl;

R 2 is H, carboxyl, substituted carboxyl, alkyl, haloalkyl, or heteroaryl;

R 5 , R 7 and R 8 are each individually H, halogen, alkoxy, alkyl, haloalkyl, aryl, nitro, cyano, amino, amido, acyl, carboxyl, substituted carboxyl, or —SO 2 R 10 , wherein R 10 is H, alkyl, amino or haloalkyl;

R 6 is halogen; and

R 3 is an optionally substituted diaryl ether.

27. The compound of claim 17 , wherein c is 1.

28. The compound of claim 14 , wherein c is 1.

29. A compound of formula I:

or a pharmaceutically acceptable salt of formula I, wherein:

R 1 is H, hydroxyl, alkoxy, acyl, alkyl, cycloalkyl, aryl, or heteroaryl;

R 2 is methyl, haloalkyl, or heteroaryl;

R 3 is trifluoromethoxy-diarylether; and

R 5 , R 6 , and R 7 and R 8 are each individually H, halogen, alkoxy, alkyl, haloalkyl, aryl, nitro, cyano, amino, amido, acyl, carboxyl, substituted carboxyl, or —SO 2 R 10 , wherein R 10 is H, alkyl, amino or haloalkyl;

provided that in formula I, R 5 and R 7 are not both H or R 6 is not H or methoxy.

30. A compound of formula I:

or a pharmaceutically acceptable salt of formula I, wherein:

R 1 is H, hydroxyl, alkoxy, acyl, alkyl, cycloalkyl, aryl, or heteroaryl;

R 2 is methyl, haloalkyl, or heteroaryl;

R 3 is

wherein R 13 and R 14 are each individually selected from at least one of alkoxy, halogen-substituted alkoxy, halogenated lower alkyl, alkyl, methylsulfonyl, or halogen; c is 0 to 5; and d is 0 to 5; and

R 5 , R 6 , and R 7 and R 8 are each individually H, halogen, alkoxy, alkyl, haloalkyl, aryl, nitro, cyano, amino, amido, acyl, carboxyl, substituted carboxyl, or —SO 2 R 10 , wherein R 10 is H, alkyl, amino or haloalkyl;

provided that in formula I, R 5 and R 7 are not both H or R 6 is not H or methoxy.

31. A compound of formula I:

or a pharmaceutically acceptable salt of formula I, wherein:

R 1 is H, hydroxyl, alkoxy, acyl, alkyl, cycloalkyl, aryl, or heteroaryl;

R 2 is methyl, haloalkyl, or heteroaryl;

R 3 is trifluoromethoxy-diarylether; and

R 5 and R 7 are each individually H, halogen, alkoxy, alkyl, haloalkyl, aryl, nitro, cyano, amino, amido, acyl, carboxyl, substituted carboxyl, or —SO 2 R 10 , wherein R 10 is H, alkyl, amino or haloalkyl;

R 6 is H, halogen, alkoxy, alkyl, haloalkyl, aryl, cyano, amino, amido, acyl, carboxyl, substituted carboxyl, or —SO 2 R 10 , wherein R 10 is H, alkyl, amino or haloalkyl; and

R 8 is H, halogen, alkoxy, haloalkyl, aryl, nitro, cyano, amino, amido, acyl, carboxyl, substituted carboxyl, or —SO 2 R 10 , wherein R 10 is H, alkyl, amino or haloalkyl;

provided that in formula I, R 6 is not H or methoxy.

32. The compound of claim 31 , wherein R 7 is methoxy.

33. The compound of claim 31 , wherein R 6 is halogen.

34. A composition comprising a pharmacologically active amount of at least one compound of claim 30 or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier.

35. The composition according to claim 34 , further comprising at least one further antimalarial agent.