US2006160799A1PendingUtilityA1
Transcription factor modulating compounds and methods of use thereof
Individually held — no corporate assignee on recordPriority: Apr 23, 2004Filed: Apr 25, 2005Published: Jul 20, 2006
Est. expiryApr 23, 2024(expired)· nominal 20-yr term from priority
A61P 43/00A61P 7/00A61P 9/00A61P 31/02A61P 27/16A61P 31/04A61P 29/00C07D 401/12C07D 413/12A61K 31/4184A61P 13/06C07D 235/24A61K 31/4709A61K 31/5377C07D 405/12A61P 1/02C07D 235/22A61K 31/42A61K 31/427C07D 235/18A61P 13/02A61P 17/10A61K 31/496C07D 417/12A61K 31/4439C07D 403/12Y02A50/30
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Claims
Abstract
Substituted benzoimidazole compounds useful as anti-infectives that decrease resistance, virulence, or growth of microbes are provided. Methods of making and using substituted benzoimidazole compounds, as well as pharmaceutical preparations thereof, in, e.g., reducing antibiotic resistance and inhibiting biofilms.
Claims
exact text as granted — not AI-modified1 . A method for reducing antibiotic resistance of a microbial cell, comprising contacting said cell with a transcription factor modulating compound of the formula (XI) (XII), (XIII), (XIV), (XV), (XVI), or (XVII):
wherein
R 1 is OH, OCOCO 2 H, a substituted or unsubstituted straight or branched C 1 -C 5 alkyloxy group, or a substituted or unsubstituted straight or branched C 1 -C 5 alkyl group;
R 4 , R 5 , R 6 , and R 7 are independently selected from the group consisting of H, (C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO 2 (C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO(substituted or unsubstituted aryl or heteroaryl), CO(C 3 -C 6 substituted or unsubstituted cycloalkyl), O(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), C(NOH)(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), substituted or unsubstituted amino, CO 2 H, CN, NO 2 , CONH 2 , (CO)(NHOH), and halogen; and
R 21a and R 21b are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 22 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 23 and R 24 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 25 and R 26 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 27 is selected from the group consisting of substituted heteroaryl; substituted alkyl; substituted or unsubstituted alkenyl; alkynyl; alkylcarbonyl, arylcarbonyl; heteroarylcarbonyl; sulfonyl; alkylamino; arylamino; heteroarylamino; alkoxy, aryloxy, heteroaryloxy; substituted straight chain C 1 -C 5 alkyl or alkenyl; substituted or unsubstituted isoxazole, thiazolidine, imidazole, quinoline, pyrrole, triazole, or pyrazine; 2-fluorophenyl, 2-methylphenyl, 2-cyanophenyl, 1-methylphenyl, and 1-fluorophenyl; and
R 28 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 29 , R 30 and R 31 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 32 is selected from the group consisting of OH, Br, CN, COH, morpholinyl, substituted aryl, substituted or unsubstituted alkenyl, alkynyl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, dialkylamino, arylamino, heteroarylamino, and aroyl;
R 33 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, dialkylamino, arylamino, heteroarylamino, aroyl and pharmaceutically acceptable salts, esters and prodrugs thereof;
provided that when R 1 is OH, R 4 , R 5 , and R 7 are H, and R 6 is NO, then R 23 is not methyl, unsubstituted phenyl, or unsubstituted furanyl;
provided that when R 1 is OH, R 4 , R 5 , and R 7 are H, and R 6 is NO, then R 25 is not unsubstituted phenyl or O-tert-butyl;
provided that when R 1 is OH, R 4 , R 5 , R 7 and R 33 are H, R 6 is NO 2 , then R 32 is not dimethylamino; and
provided that when R 1 is OH, R 4 , R 5 , R 7 and R 33 are H, R 6 is Br, then R 32 is not dimethylamino;
such that the antibiotic resistance of said cell is reduced.
2 . A method for modulating transcription, comprising contacting a transcription factor with a transcription factor modulating compound of the formula (XI), (XII), (XIII), (XIV), (XV), (XVI), or (XVII):
wherein
R 1 is OH, OCOCO 2 H, a substituted or unsubstituted straight or branched C 1 -C 5 alkyloxy group, or a substituted or unsubstituted straight or branched C 1 -C 5 alkyl group;
R 4 , R 5 , R 6 , and R 7 are independently selected from the group consisting of H, (C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO 2 (C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO(substituted or unsubstituted aryl or heteroaryl), CO(C 3 -C 6 substituted or unsubstituted cycloalkyl), O(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), C(NOH)(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), substituted or unsubstituted amino, CO 2 H, CN, NO 2 , CONH 2 , (CO)(NHOH), and halogen; and
R 21a and R 21b are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 22 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 23 and R 24 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 25 and R 26 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 27 is selected from the group consisting of substituted heteroaryl; substituted alkyl; substituted or unsubstituted alkenyl; alkynyl; alkylcarbonyl, arylcarbonyl; heteroarylcarbonyl; sulfonyl: alkylamino; arylamino; heteroarylamino; alkoxy, aryloxy, heteroaryloxy; substituted straight chain C 1 -C 5 alkyl or alkenyl; substituted or unsubstituted isoxazole, thiazolidine, imidazole, quinoline, pyrrole, triazole, or pyrazine; 2-fluorophenyl, 2-methylphenyl, 2-cyanophenyl, 1-methylphenyl, and 1-fluorophenyl, and
R 28 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 29 , R 30 and R 31 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 32 is selected from the group consisting of OH, Br, CN, CO 2 H, morpholinyl, substituted aryl, substituted or unsubstituted alkenyl, alkynyl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, dialkylamino, arylamino, heteroarylamino, and aroyl;
R 33 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, dialkylamino, arylamino, heteroarylamino, aroyl and pharmaceutically acceptable salts, esters and prodrugs thereof;
provided that when R 1 is OH, R 4 , R 5 , and R 7 are H, and R 6 is NO 2 , then R 23 is not methyl, unsubstituted phenyl, or unsubstituted furanyl;
provided that when R 1 is OH, R 4 , R 5 , and R 7 are H, and R 6 is NO 2 , then R 25 is not unsubstituted phenyl or O-tert-butyl:
provided that when R 1 is OH, R 4 , R 5 , R 7 and R 33 are H, R 6 is NO 2 , then R 32 is not dimethylamino; and
provided that when R 1 is OH, R 4 , R 5 , R 7 and R 33 are H, R 6 is Br, then R 32 is not dimethylamino;
such that the transcription is modulated.
3 .- 8 . (canceled)
9 . The method of claim 1 , wherein R 1 is OH.
10 . The method claim 1 , wherein R 4 , R 5 , R 7 and R 26 are each H.
11 . The method of claim 1 , wherein R 6 is NO 2 .
12 . The method of claim 1 , wherein R 25 is a substituted alkenyl group.
13 . The method of claim 12 , wherein said substituted alkenyl group is substituted with substituted or unsubstituted phenyl.
14 . The method of claim 13 , wherein said substituted phenyl is para-halogenated phenyl.
15 . The method of claim 14 , wherein said substituted phenyl is para-fluorophenyl.
16 - 77 . (canceled)
78 . The method of claim 1 , wherein the transcription factor modulating compound is:
79 . The method of claim 1 , wherein said transcription factor is a transcriptional activation factor.
80 . The method of claim 79 , wherein said transcriptional activation factor is an AraC family polypeptide.
81 . The method of claim 79 , wherein said transcriptional activation factor is a MarA family polypeptide.
82 . The method of claim 1 , wherein said transcription factor modulating compound is a transcription factor inhibiting compound.
83 . The method of claim 1 , wherein said transcription factor is prokaryotic.
84 . The method of claim 81 , wherein said MarA family polypeptide is MarA, SoxS, Rob or LcrF (VirF).
85 . The method of claim 1 , wherein said transcription factor modulating compound has an EC 50 activity against SoxS of less than 10 μM.
86 - 96 . (canceled)
97 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a transcription factor modulating compound, wherein said compound is of the formula (XI), (XII), (XIII), (XIV), (XV), (XVI), or (XVII):
wherein
R 1 is OH, OCOCO 2 H, a substituted or unsubstituted straight or branched C 1 -C 5 alkyloxy group, or a substituted or unsubstituted straight or branched C 1 -C 5 alkyl group;
R 4 , R 5 , R 6 , and R 7 are independently selected from the group consisting of H, (C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO 2 (C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO(substituted or unsubstituted aryl or heteroaryl), CO(C 3 -C 6 substituted or unsubstituted cycloalkyl), O(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), C(NOH)(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), substituted or unsubstituted amino, CO 2 H, CN, NO 2 , CONH 2 , (CO)(NHOH), and halogen; and
R 21a and R 21b are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 22 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 23 and R 24 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 25 and R 26 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 27 is selected from the group consisting of substituted heteroaryl; substituted alkyl; substituted or unsubstituted alkenyl; alkynyl; alkylcarbonyl, arylcarbonyl; heteroarylcarbonyl; sulfonyl; alkylamino; arylamino; heteroarylamino; alkoxy, aryloxy, heteroaryloxy; substituted straight chain C 1 -C 5 alkyl or alkenyl; substituted or unsubstituted isoxazole, thiazolidine, imidazole, quinoline, pyrrole, triazole, or pyrazine; 2-fluorophenyl, 2-methylphenyl, 2-cyanophenyl, 1-methylphenyl, and 1-fluorophenyl; and
R 28 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 29 , R 30 and R 31 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 32 is selected from the group consisting of OH, Br, CN, CO 2 H, morpholinyl, substituted aryl, substituted or unsubstituted alkenyl, alkynyl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, dialkylamino, arylamino, heteroarylamino, aroyl;
R 33 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, dialkylamino, arylamino, heteroarylamino, and aroyl;
provided that when R 1 is OH, R 4 , R 5 , R 7 and R 33 are H, R 6 is NO 2 , then R 32 is not dimethylamino;
provided that when R 1 is OH, R 4 , R 5 , R 7 and R 33 are H, R 6 is Br, then R 32 is not dimethylamino;
provided that when R 1 is OH, R 4 , R 5 , and R 7 are H, and R 6 is NO 2 , then R 25 is not unsubstituted phenyl or O-tert-butyl;
provided that when R 1 is OH, R 4 , R 5 , and R 7 are H, and R 6 is NO 2 , then R 23 is not methyl, unsubstituted phenyl, or unsubstituted furanyl, or a pharmaceutically acceptable salt, ester or prodrug thereof.
98 - 109 . (canceled)
110 . A method for preventing a bacterial associated state in a subject, comprising administering to said subject an effective amount of a transcription factor modulating compound of the formula (XI), (XII), (XIII), (XIV), (XV), (XVI), or (XVII):
wherein
R 1 is OH, OCOCO 2 H, a substituted or unsubstituted straight or branched C 1 -C 5 alkyloxy group, or a substituted or unsubstituted straight or branched C 1 -C 5 alkyl group;
R 4 , R 5 , R 6 , and R 7 arc independently selected from the group consisting of H, (C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO 2 (C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO(substituted or unsubstituted aryl or heteroaryl), CO(C 3 -C 6 substituted or unsubstituted cycloalkyl), O(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), C(NOH)(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), substituted or unsubstituted amino, CO 2 H, CN, NO 2 , CONH 2 , (CO)(NHOH), and halogen; and
R 21a and R 21b are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 22 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 23 and R 24 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 25 and R 26 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 27 is selected from the group consisting of substituted heteroaryl; substituted alkyl; substituted or unsubstituted alkenyl; alkynyl; alkylcarbonyl, arylcarbonyl; heteroarylcarbonyl; sulfonyl; alkylamino; arylamino; heteroarylamino; alkoxy, aryloxy, heteroaryloxy; substituted straight chain C 1 -C 5 alkyl or alkenyl; substituted or unsubstituted isoxazole, thiazolidine, imidazole, quinoline, pyrrole, triazole, or pyrazine; 2-fluorophenyl, 2-methylphenyl, 2-cyanophenyl, 1-methylphenyl, and 1-fluorophenyl; and
R 28 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 29 , R 30 and R 31 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 32 is selected from the group consisting of OH, Br, CN, CO 2 H, morpholinyl, substituted aryl, substituted or unsubstituted alkenyl, alkynyl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, dialkylamino, arylamino, heteroarylamino, aroyl;
R 33 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, dialkylamino, arylamino, heteroarylamino, and aroyl;
provided that when R 1 is OH, R 4 , R 5 , R 7 and R 33 are H, R 6 is NO 2 , then R 32 is not dimethylamino;
provided that when R 1 is OH, R 4 , R 5 , R 7 and R 33 are H, R 6 is Br, then R 32 is not dimethylamino;
provided that when R 1 is OH, R 4 , R 5 , and R 7 are H, and R 6 is NO 2 , then R 25 is not unsubstituted phenyl or O-tert-butyl;
provided that when R 1 is OH, R 4 , R 5 , and R 7 are H, and R 6 is NO 2 , then R 23 is not methyl, unsubstituted phenyl, or unsubstituted furanyl, or a pharmaceutically acceptable salt, ester or prodrug thereof, such that the bacterial associated state in said subject is prevented.
111 . The method of claim 110 , wherein said subject is a human.
112 - 115 . (canceled)
116 . A compound of the formula (XI), (XII) (XIII), (XIV), (XV), (XVI), or (XVII):
wherein
R 1 is OH, OCOCO 2 H, a substituted or unsubstituted straight or branched C 1 -C 5 alkyloxy group, or a substituted or unsubstituted straight or branched C 1 -C 5 alkyl group;
R 4 , R 5 , R 6 , and R 7 are independently selected from the group consisting of H, (C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO 2 (C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), CO(substituted or unsubstituted aryl or heteroaryl), CO(C 3 -C 6 substituted or unsubstituted cycloalkyl), O(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), C(NOH)(C 1 -C 5 substituted or unsubstituted, straight or branched alkyl), substituted or unsubstituted amino, CO 2 H, CN, NO 2 , CONH 2 , (CO)(NHOH), and halogen; and
R 21a and R 21b are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 22 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 23 and R 24 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 25 and R 26 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl;
R 27 is selected from the group consisting of substituted heteroaryl; substituted alkyl; substituted or unsubstituted alkenyl; alkynyl; alkylcarbonyl, arylcarbonyl;
heteroarylcarbonyl; sulfonyl; alkylamino; arylamino; heteroarylamino; alkoxy, aryloxy heteroaryloxy; substituted straight chain C 1 -C 5 alkyl or alkenyl; substituted or unsubstituted isoxazole, thiazolidine, imidazole, quinoline, pyrrole, triazole, or pyrazine, 2-fluorophenyl, 2-methylphenyl, 2-cyanophenyl, 1-methylphenyl, and 1-fluorophenyl, and
R 28 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl,
R 29 , R 30 and R 31 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, arylamino, heteroarylamino, and aroyl,
R 32 is selected from the group consisting of OH, Br, CN, COH, morpholinyl, substituted aryl, substituted or unsubstituted alkenyl, alkynyl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, dialkylamino, arylamino, heteroarylamino, and aroyl,
R 33 is selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylsulfonyl, arylsulfonyl, aminosulfonyl, alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, acyl, acylamino, alkylamino, dialkylamino, arylamino, heteroarylamino, aroyl and pharmaceutically acceptable salts, esters and prodrugs thereof;
provided that when R 1 is OH, R 4 , R 5 , and R 7 are H, and R 6 is NO 2 , then R 23 is not methyl, unsubstituted phenyl, or unsubstituted furanyl;
provided that when R 1 is OH, R 4 , R 5 , and R 7 are H, and R 6 is NO_, then R 25 is not unsubstituted phenyl or O-tert-butyl,
provided that when R 1 is OH, R 4 , R 5 , R 7 and R 33 are H, R 6 is NO 2 , then R 32 is not dimethylamino; and
provided that when R 1 is OH, R 4 , R 5 , R 7 and R 33 are H, R 6 is Br, then R 32 is not dimethylamino.
117 - 172 . (canceled)
173 . A compound of 116 , wherein the formula of the compound is:
or a pharmaceutically acceptable, salt, prodrug or ester thereof.Join the waitlist — get patent alerts
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