3-glyoxylamideindoles for treating cancer

1 - 20 . (canceled)

21 . A method of treating a subject with cancer, said method comprising administering to the subject an effective amount of a compound represented by the following structural formula:

or a pharmaceutically acceptable salt thereof, wherein:

Ring A is substituted or unsubstituted and is optionally fused to an aryl group;

Z 1 and Z 2 are independently ═O or ═S;

R 1 is —H, an aliphatic group, a substituted aliphatic group, an unsubstituted aryl group or a substituted aryl group;

R 2 is an aryl group substituted with —C(O)—NR 5 R 6 , —S(O) 2 R 5 R 6 or —S(O) 2 R 5 R 6 or is represented by a structural formula selected from:

R 3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted aliphatic group;

R 4 is —H, a substituted alkyl group or an unsubstituted alkyl group;

R 5 and R 6 are independently —H, an aliphatic group, a substituted aliphatic group, an unsubstituted non-aromatic heterocylic group, a substituted non-aromatic heterocylic group, an unsubstituted aryl group or a substituted aryl group; or —NR 5 R 6 , taken together, is a substituted or unsubstituted non-aromatic nitrogen-containing heterocyclic group or a substituted or unsubstituted nitrogen-containing heteroaryl group;

X is a covalent bond, —C(R 7 R 8 )—, —N(R 7 )—, —O—, —S—, —S(O)—, —S(O) 2 —, —C(═O)—, − C(═O)—N(R 4 )—, or —N(R 7 )—C(═O)—;

R 7 and R 9 are independently —H or a substituted or unsubstituted aliphatic group, wherein the cancer is selected from the group consisting of uterine cancer, leukemia and breast cancer.

22 . The method of claim 21 wherein R 2 is an aryl group substituted with —C(O)—NR 5 R 6 or is represented by a structural formula selected from:

23 . The method of claim 22 wherein:

Ring A is substituted or unsubstituted;

Z 1 and Z 2 are both ═O;

R 1 and R 4 are both —H;

R 3 is a substituted or unsubstituted aryl group; and

X is a —C(R 7 R 8 )—, —N(R 7 )— and —O—.

24 . The method of claim 23 wherein X is —C(R 7 R 8 )—.

25 . The method of claim 24 wherein R 3 is a substituted or unsubstituted phenyl or pyridyl group and R 7 and R 8 are both —H.

26 . The method of claim 25 wherein zero, one or more ring carbons atoms of Rings B-P are substituted with a group independently selected from —OH, —Br, —Cl, —I, —F, —OR a , —O—COR a , —COR a , —CN, —NO 2 , —COOH, —SO 3 H, —NH 2 , —NHR a , —N(R a R b ), —COOR a , —CHO, —CONH 2 , —CONHR a , —CON(R a R b ), —NHCOR a , —NRCOR a , —NHCONH 2 , —NHCONR a H, —NHCON(R a R b ), —NR c CONH 2 , —NR c CONR a H, —NR c CON(R a R b ), —C(═NH)—NH 2 , —C(═NH)—NHR a , —C(═NH)—N(R a R b ), —C(═NR c )—NH 2 , —C(═NR c )—NHR a , —C(═NR c )—N(R a R b ), —NH—C(═NH)—NH 2 , —NH—C(═NH)—NHR a , —NH—C(═NH)—N(R a R b ), —NH—C(═NR c )—NH 2 , —NH—C(═NR c )—NHR a , —NH—C(═NR c )—N(R a R b ), —NR d H—C(═NH)—NH 2 , —NR d —C(═NH)—NHR a , —NR d —C(═NH)—N(R a R b ), —NR d —C(═NR c )—NH 2 , NR d —C(═NR c )—NHR a , NR d —C(═NR c )—N(R a R b ), —NHNH 2 , —NHNHR a , NHR a R b , —SO 2 NH 2 , —SO 2 NHR a , —SO 2 NR a R b , —CH═CHR a , —CH═CR a R b , —CR c ═CR a R b , —CR c ═CHR a , —CR c ═CR a R b , —CCR a , —SH, —SR a , —S(O)R a , —S(O) 2 R a , alkyl groups, substituted alkyl group, non-aromatic heterocyclic group, substituted non-aromatic heterocyclic group, benzyl group, substituted benzyl group, aryl group or substituted aryl group wherein R a -R d are each independently an alkyl group, substituted alkyl group, benzyl, substituted benzyl, aryl or substituted aryl group, or, —NR a R d , taken together, can also form a substituted or unsubstituted non-aromatic heterocyclic group.

27 . The method of claim 26 wherein zero one or more ring carbon atoms of Rings B-P are independently substituted with a group selected from C1-C4 alkyl, C1-C4 hydroxyalkyl, N-morpholino, pyrimidyl, C1-C4 alkyl substituted with pyrimidyl, —NH(C1-C4 alkyl), —N(C1-C4 alkyl) 2 , —C(O)NH 2 , —C(O)NH(C1-C4 alkyl), C(O)N(C1-C4 alkyl) 2 , —NHC(O)(C1-C4 alkyl), —NO 2 , C1-C4 alkoxy, —C(O)O—CH 2 CH 2 —N(C1-C4 alkyl) 2 , —C(O)O—CH 2 CH 2 —NH(C1-C4 alkyl),

—NH-(phenyl), —NH 2 , —CH 2 NH—C(O)—O—(C1-C4 alkyl), —CH 2 NH 2 , —Cl, —F, —C(O)—O—(C1-C4 alkyl), —C(O)—NH—(C1-C4 alkyl), C3-C7 cycloalkyl, phenyl, —C(O)—N-morpholino, —S—(C1-C4 alkyl), —CN, furyl, —S(O) 2 —(C 1 -C 4 alkyl), —S(O) 2 —NH 2 , —S(O) 2 —NH(C1-C4 alkyl), —S(O) 2 —N(C1-C4 alkyl) 2 .

28 . The method of claim 26 wherein R 2 is represented by a structural formula selected from:

wherein X 2 is —N— or —CH— and R 12 and R 13 are independently a C1-C4 alkyl group.

29 . The method of claim 28 wherein R 5 and R 6 are independently —H or a C1-C4 alkyl group.

30 . The method of claim 29 wherein Ring A is optionally substituted with one or more groups selected from —F, —Cl, —Br, —C1-C4 alkyl, C1-C4 alkoxy, —C1-C4 haloalkyl, C 1 -C 4 haloalkoxy, —CN or —NH 2 .

31 . The method of claim 30 wherein:

R 3 is a phenyl or pyridyl group substituted with zero, one or more groups selected from —Br, —Cl, —F, —R e , —OR e , —CH 3 , —CF 3 , —CN, —COOR e , —N(R e ) 2 , —CON(R e ) 2 , —NR e COR f , —NHCONH 2 , —SO 2 R e and —SO 2 N(R e ) 2 ; and

each R e and R f are independently selected from —H, alkyl or substituted alkyl.

32 . The method of claim 31 wherein R 3 is a phenyl group substituted with zero, one or more groups selected from —Cl, —F, —R e , —OR e , —CN, —NH 2 , —CONH 2 or —NHCOR f .

33 . The method of claim 32 wherein R 3 is a phenyl group substituted with zero, one or more groups selected from —CH 3 , —CH 2 CH 3 , —F, —Cl, —CN or —OCH 3 and R 5 and R 6 are both —H.

34 . The method of claim 33 wherein R 3 is represented by the following structural formula:

R 14 is —CH 3 , —CH 2 CH 3 , —OCH 3 , —CN, —F or —Cl.

35 . The method of claim 34 wherein Ring A is unsubstituted.

36 - 42 . (canceled)

43 . A method of treating a subject with cancer, said method comprising administering to the subject an effective amount of a compound represented by the following structural formula:

or a pharmaceutically acceptable salt thereof, wherein:

Ring A is substituted or unsubstituted and is optionally fused to an aryl group;

Z 1 and Z 2 are independently ═O or ═S;

R 1 is —H, an aliphatic group, a substituted aliphatic group, an unsubstituted aryl group or a substituted aryl group;

R 3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted aliphatic group;

R 4 is —H, a substituted alkyl group or an unsubstituted alkyl group;

X is a covalent bond, —C(R 7 R 8 )—, —N(R 7 )—, —O—, —S—, —S(O)—, —S(O) 2 —, —C(═O)—, —C(═O)—N(R 4 )—, or —N(R 7 )—C(═O)—;

R 7 and R 8 are independently —H or a substituted or unsubstituted aliphatic group; and

Ring B is substituted or unsubstituted,

wherein the cancer is selected from the group consisting of uterine cancer, leukemia and breast cancer.

44 . The method of claim 43 wherein:

Ring A is substituted or unsubstituted;

Z 1 and Z 2 are both ═O;

R 1 and R 4 are both —H;

R 3 is a substituted or unsubstituted aryl group; and

X is a —C(R 7 R 8 )—, —N(R 7 )— and —O—.

45 . The method of claim 44 wherein X is —C(R 7 R 8 )—.

46 . The method of claim 45 wherein R 3 is a substituted or unsubstituted phenyl or pyridyl group and R 7 and R 8 are both —H.

47 . The method of claim 46 wherein zero, one or more ring carbons atoms of Ring B is substituted with a group independently selected from —OH, —Br, —Cl, —I, —F, —OR a , —O—COR a , —COR a , —CN, —NO 2 , —COOH, —SO 3 H, —NH 2 , —NHR a , —N(R a R b ), —COOR a , —CHO, —CONH 2 , —CONHR a , —CON(R a R b ), —NHCOR a , —NRCOR a , —NHCONH 2 , —NHCONR a H, —NHCON(R a R b ), —NR c CONH 2 , —NR c CONR a H, —NR c CON(R a R b ), —C(═NH)—NH 2 , —C(═NH)—NHR a , —C(═NH)—N(R a R b ), —C(═NR c )—NH 2 , C(═NR c )—NHR a , —C(═NR c )—N(R a R b ), —NH—C(═NH)—NH 2 , —NH—C(═NH)—NHR a , —NH—C(═NH)—N(R a R b ), —NH—C(═NR c )—NH 2 , —NH—C(═NR c )—NHR a , —NH—C(═NR c )—N(R a R b ), —NR d H—C(═NH)—NH 2 , —NR d —C(═NH)—NHR a , —NR d —C(═NH)—N(R a R b ), —NR d —C(═NR c )—NH 2 , —NR d —C(═NR c )—NHR a , —NR d —C(═NR c )—N(R a R b ), —NHNH 2 , —NHNHR a , —NHR a R b , —SO 2 NH 2 , —SO 2 NHR a , —SO 2 NR a R b , —CH═CHR a , —CH═CR a R b , —CR c ═CR a R b , —CR c ═CHR a , —CR c ═CR a R b , —CCR a , —SH, —SR a , —S(O)R a , —S(O) 2 R a , alkyl groups, substituted alkyl group, non-aromatic heterocyclic group, substituted non-aromatic heterocyclic group, benzyl group, substituted benzyl group, aryl group or substituted aryl group wherein R a -R d are each independently an alkyl group, substituted alkyl group, benzyl, substituted benzyl, aryl or substituted aryl group, or, —NR a R d , taken together, can also form a substituted or unsubstituted non-aromatic heterocyclic group.

48 . The method of claim 47 wherein R 2 is represented by the following structural formula:

wherein X 2 is —N— or —CH— and R 13 are independently a C1-C4 alkyl group.

49 . The method of claim 48 wherein R 5 and & are independently —H or a C1-C4 alkyl group.

50 . The method of claim 49 wherein Ring A is optionally substituted with one or more groups selected from —F, —Cl, —Br, —C1-C4 alkyl, C1-C4 alkoxy, —C1-C4 haloalkyl, C1-C4 haloalkoxy, —CN or —NH 2 .

51 . The method of claim 50 wherein:

R 3 is a phenyl or pyridyl group substituted with zero, one or more groups selected from —Br, —Cl, —F, —R e , —OR e , —CH 3 , —CF 3 , —CN, —COOR e , —N(R e ) 2 , —CON(R e ) 2 , —NR e COR f , —NHCONH 2 , —SO 2 R e and —SO 2 N(R e ) 2 ; and

each R e and R f are independently selected from —H, alkyl or substituted alkyl.