Antivirals against molluscum contagiosum virus

1. A compound of formula (X) or (XII):

wherein:

Y is heteroaryl; which is substituted with at least one group selected from the group consisting of phenyl and heteroaryl;

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from the group consisting of H, C 1 -C 6 alkyl, halo, cyano, nitro, SO 2 NH 2 , C 1 -C 6 haloalkyl, OR a , SR a , NR m R n , NR a COR b , SOR b , SO 2 R b , COR b , COOR a , aryl, heteroaryl, C 3 -C 7 cycloalkyl, 3-7 membered heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl; or two adjacent OR a or NR m R n groups, together with the atoms to which they are attached, form a 5-7 membered heterocycloalkyl group;

R 14 is H, C 1 -C 3 alkyl, C(O)OR a , C(O)R b , C(O)NR m R n , SOR b , or SO 2 R b ;

R a and R b are each independently selected from the group consisting of H, C 1 - 6 alkyl, C 1-6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl;

R m and R n are independently selected from the group consisting of H, C 1 -C 6 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl; or R m and R n , together with the nitrogen atom to which they are attached, form a 3-7 membered heterocycloalkyl group;

each occurrence of aryl is independently selected from the group consisting of phenyl and naphthyl; and

each occurrence of heteroaryl is independently selected from the group consisting of pyridine, pyrimidine, pyrazine, indole, indolizine, benzimidazole, 1,3-dihydrobenzimidazol-2-one, and indazole.

2. The compound of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from the group consisting of H, halo, cyano, nitro, CF 3 , and SO 2 NH 2 .

3. The compound of claim 1 , wherein Y is pyridine.

4. The compound of claim 1 , wherein R 14 is H or C 1 -C 3 alkyl.

5. The compound of claim 1 , wherein Y is substituted with at least one heteroaryl.

6. A compound selected from the group consisting of:

5-[(2-benzyloxyphenyl)methylamino]-1,3-dihydrobenzimidazol-2-one,

5-[[2-[(4-chlorophenyl)methoxy]phenyl]methylamino]-1,3-dihydrobenzimidazol-2-one,

5-[[2-[(2-chlorophenyl)methoxy]phenyl]methylamino]-1,3-dihydrobenzimidazol-2-one,

5-[[2-[(4-fluorophenyl)methoxy]phenyl]methylamino]-1,3-dihydrobenzimidazol-2-one,

5-[(2-benzyloxy-5-bromo-phenyl)methylamino]-1,3-dihydrobenzimidazol-2-one,

5-[[5-chloro-2-[(2-fluorophenyl)methoxy]phenyl]methylamino]-1,3dihydrobenzimidazol-2-one,

N-[(2-benzyloxyphenyl)methyl]-1H-indazol-5-amine,

4-[[5-bromo-2-[(4-fluorophenyl)methoxy]phenyl]methylamino]phenol,

4-[(2-benzyloxy-5-chloro-phenyl)methyl amino]benzene sulfonamide,

4-[(2-benzyloxy-5-chloro-phenyl)methyl amino]benzene sulfonamide,

4-[[2-[(3-nitrophenyl)methoxy]phenyl]methyl amino]phenol,

2-[[2-[(3-nitrophenyl)methoxy]phenyl]methyl amino]phenol,

4-[(2-benzyloxyphenyl)methylamino]-3-fluoro-phenol, or

N-[(2-benzyloxyphenyl)methyl]-4-oxazol-5-yl-aniline;

or a salt thereof.

7. A pharmaceutical composition comprising the compound of claim 6 , or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier.

8. A method of inhibiting, treating, or abrogating a molluscum contagiosum virus infection in a subject in need thereof, the method comprising administering to said subject a therapeutically effective amount of a compound of formula (IX), or a pharmaceutically acceptable salt thereof:

wherein:

A, Z, and Y is aryl or heteroaryl, each optionally substituted with C 1 -C 6 alkyl, halo, cyano, nitro, C 1 -C 6 haloalkyl, OR a , SR a NR m R n , NR a COR b , SOR b , SO 2 R b , COR b , COOR a , aryl, heteroaryl, C 3 -C 7 cycloalkyl, 3-7 membered heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, or heteroarylalkyl; or two adjacent OR a or NR m R n groups, together with the atoms to which they are attached, form a 5-7 membered heterocycloalkyl group;

R 14 is H, C 1 -C 3 alkyl, C(O)OR a , C(O)R b , C(O)NR m R n , SOR b , or SO 2 R b ;

R a and R b are each independently selected from the group consisting of H, C 1-6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl; and

R m and R n are independently selected from the group consisting of H, C 1 -C 6 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl; or R m and R n , together with the nitrogen atom to which they are attached, form a 3-7 membered heterocycloalkyl group.

9. The method of claim 8 , wherein the compound is a compound of formula (X) or (XII):

wherein:

Y is heteroaryl; and

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from the group consisting of H, C 1 -C 6 alkyl, halo, cyano, nitro, SO 2 NH 2 , C 1 -C 6 haloalkyl, OR a , SR a NR m R n , NR a COR b , SOR b , SO 2 R b , COR b , COOR a , aryl, heteroaryl, C 3 -C 7 cycloalkyl, 3-7 membered heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl; or two adjacent OR a or NR m R n groups, together with the atoms to which they are attached, form a 5-7 membered heterocycloalkyl group.

10. The method of claim 9 , wherein Y is pyridine, pyrimidine, pyrazine, indole, indolizine, benzimidazole, 1,3-dihydrobenzimidazol-2-one, or indazole.

11. The method of claim 9 , wherein the compound is a compound of formula (XI):

12. The method of claim 8 , wherein the compound is a compound of formula (XIII) or (XIV):

wherein:

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , and R 16 are independently selected from the group consisting of H, C 1 -C 6 alkyl, halo, cyano, nitro, SO 2 NH 2 , C 1 -C 6 haloalkyl, OR a , SR a NR m R n , NR a COR b , SOR b , SO 2 R b , COR b , COOR a , aryl, heteroaryl, C 3 -C 7 cycloalkyl, 3-7 membered heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl; or two adjacent OR a or NR m R n groups, together with the atoms to which they are attached, form a 5-7 membered heterocycloalkyl group.

13. A method of inhibiting, treating, or abrogating a molluscum contagiosum virus infection in a subject in need thereof, the method comprising administering to said subject a therapeutically effective amount of a compound selected from the group consisting of:

5-[(2-benzyloxyphenyl)methylamino]-1,3-dihydrobenzimidazol-2-one,

5-[[2-[(4-chlorophenyl)methoxy]phenyl]methylamino]-1,3-dihydrobenzimidazol-2-one,

5-[[2-[(2-chlorophenyl)methoxy]phenyl]methylamino]-1,3-dihydrobenzimidazol-2-one,

5-[[2-[(4-fluorophenyl)methoxy]phenyl]methylamino]-1,3-dihydrobenzimidazol-2-one,

5-[(2-benzyloxy-5-bromo-phenyl)methylamino]-1,3-dihydrobenzimidazol-2-one,

5-[[5-chloro-2-[(2-fluorophenyl)methoxy]phenyl]methylamino]-1,3-dihydrobenzimidazol-2-one,

N-[(2-benzyloxyphenyl)methyl]-1H-indazol-5-amine,

4-[[5-bromo-2-[(4-fluorophenyl)methoxy]phenyl]methylamino]phenol,

4-[(2-benzyloxy-5-chloro-phenyl)methylamino]benzenesulfonamide,

4-[[2-[(3-nitrophenyl)methoxy]phenyl]methylamino]phenol,

2-[[2-[(3-nitrophenyl)methoxy]phenyl]methylamino]phenol,

4-[(2-benzyloxyphenyl)methylamino]phenol,

4-[(2-benzyloxyphenyl)methylamino]-3-fluoro-phenol, or

N-[(2-benzyloxyphenyl)methyl]-4-oxazol-5-yl-aniline; or a salt thereof.

14. A method of inhibiting, treating, or abrogating a molluscum contagiosum virus infection in a subject in need thereof, the method comprising administering to said subject a therapeutically effective amount of a compound of formula (I), or a pharmaceutically acceptable salt thereof:

wherein:

R 14 is H, C 1 -C 3 alkyl, C(O)OR a , C(O)R b , C(O)NR m R n , SOR b , or SO 2 R b ;

R 15 is H, C 1 -C 5 alkyl, C(O)R a , or C(O)NR m R n ;

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are independently selected from the group consisting of H, C 1 -C 6 alkyl, halo, cyano, nitro, SO 2 NH 2 ,C 1 -C 6 haloalkyl, OR a , SR a , NR m R n , NR a COR b , SOR b , SO 2 R b , COR b , COOR a , aryl, heteroaryl, C 3 -C 7 cycloalkyl, 3-7 membered heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl;

R a and R b are each independently selected from the group consisting of H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl;

R m and R n are independently selected from the group consisting of H, C 1 -C 6 alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl; or R m and R n , together with the nitrogen atom to which they are attached, form a 3-7 membered heterocycloalkyl group.

15. The method of claim 14 , wherein the compound is selected from the group consisting of a compound of formula (II):

a compound of formula (III):

a compound of formula (IV):

a compound of formula (V):

a compound of formula (VI):

a compound of formula (VII):

a compound of formula (VIII):

16. The method of claim 8 , wherein the compound is administered topically to the subject.