Benzoquinone ansamycins

A compound or pharmaceutically acceptable salt or prodrug thereof having the formula:

• 14
• wherein R1 is MeO, (CH2)3N or R9—NH, wherein R9 is selected from the group consisting of H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkenyl, substituted or unsubstituted C1-C6 alkynyl, substituted or unsubstituted C3-C6 cycloalkyl, piperidinyl, N-alkylpiperidinyl, hexahydropyranyl, furfuryl, tetrahydrofurfuryl, pyrrolidinyl, N-alkylpyrrolidinyl, piperazinylamino, N-alkylpiperazinyl, morpholinyl, N-alkylaziridinylmethyl, (1-azabicyclo[1.3.0]hex-1-yl)ethyl, 2-(N-methyl-pyrrolidin-2-yl)ethyl, 2-(4-imidazolyl)ethyl, 2-(1-methyl-4-imidazolyl)ethyl, 2-(1-methyl-5-imidazolyl)ethyl, 2-(4-pyridyl)ethyl, and 3-(4-morpholino)-1-propyl, or R6 is H and R1 and R5 taken together form a group of the formula NH—Z—O, wherein Z is a linker comprised of from 1 to 6 carbon atoms and 0 to 2 nitrogen atoms and wherein the O is attached at the position of R5;
• R2 is selected from the group consisting of H, halogen, OR10, NHR10, SR10, aryl, and heteroaryl, wherein R10 is selected from the group consisting of substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkenyl, substituted or unsubstituted C1-C6 alkynyl, and substituted or unsubstituted C3-C6 cycloalkyl;
• R3 is H, OH, or OMe;
• R4 is H or Me;
• R5 is OH or O—C(═O)—CH2NH2 and R6 is H, or R5 and R6 taken together form ═O or ═N—OR11, wherein R11 is selected from the group consisting of H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkenyl, substituted or unsubstituted C1-C6 alkynyl, substituted or unsubstituted C3-C6 cycloalkyl, aryl, or heteroaryl;
• R7 is H and R8 is H or OH, or R7 and R8 taken together form a bond;
• and X is O or a bond, with the provisos that when R3 is H, R4 is Me, and R7 is H and R8 is H or R7 and R8 taken together form a bond that either R6 is H and R1 and R5 taken together form a group of the formula NH—Z—O, wherein Z is a linker comprised of from 1 to 6 carbon atoms and 0 to 2 nitrogen atoms and wherein the O is attached at the position of R5, or that R1 is (CH2)3N or R9—NH, wherein R9 is selected from the group consisting of piperidinyl, N-alkylpiperidinyl, hexahydropyranyl, furfuryl, tetrahydrofurfuryl, pyrrolidinyl, N-alkylpyrrolidinyl, piperazinylamino, N-alkylpiperazinyl, morpholinyl, N-alkylaziridinylmethyl, (1-azabicyclo[1.3.0]hex-1-yl)ethyl, 2-(N-methyl-pyrrolidin-2-yl)ethyl, 2-(4-imidazolyl)ethyl, 2-(1-methyl-4-imidazolyl)ethyl, 2-(1-methyl-5-imidazolyl)ethyl, 2-(4-pyridyl)ethyl, and 3-(4-morpholino)-1-propyl;
• and that when R3 is H and R4 is Me that R7 is H and R8 is OH.