主权项 |
1. An isolated therapeutic having a structure of formula I as follows: wherein: the carbohydrate anomeric carbon designated * is in the R or S configuration; R1 is selected from the group consisting of H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —(CH2)nC(O)R11, —(CH2)nOC(O)R11, —(CH2)nC(O)2R11, —(CH2)nC(O)NR12R13, —(CH2)nOC(O)NR12R13, arylalkyl, heteroarylalkyl, a benzyl ether moiety, a carbamate moiety, an ═NR14 moiety, and a carbonate moiety, wherein each of C1-C6 alkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —(CH2)nC(O)R11, —(CH2)nOC(O)R11, —(CH2)nC(O)2R11, —(CH2)nC(O)NR12R13, —(CH2)nOC(O)NR12R13, arylalkyl, and heteroarylalkyl is optionally substituted with from 1 to 3 substituents independently selected at each occurrence thereof from C1-C3 alkyl, halogen, —CN, —OR12, —NR12R13, an amino acid group, and phenyl which is optionally substituted 1-3 times with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, —CN, —NO2, —OR12, or —NR12R13; R2 is selected from the group consisting of H, —OR12, —NR12R13, —(CH2)nC(O)R11, —(CH2)nC(O)NR12R13, —(CH2)nOC(O)NR12R13, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, phenyl, benzyl, a benzyl ether moiety, a carbamate moiety, an ═NR14 moiety, and a carbonate moiety, wherein each of —(CH2)nC(O)R11, —(CH2)nC(O)NR12R13, C1-C6 alkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, phenyl, and benzyl is optionally substituted 1 to 3 times with halogen, cyano, —NO2, —NR12R13, —OR12, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or an amino acid group; R3 is selected from the group consisting of H, halogen, —OR12, —NR12R13, —NR12C(O)R13, —NR12C(O)2R13, —NR12C(O)NR12R13, —S(O)qR12, —CN, —NO2, —(CH2)nC(O)R11, —(CH2)nC(O)2R11, —(CH2)nC(O)NR12R13, —(CH2)nOC(O)NR12R13, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, heterocyclyl, aryl, heteroaryl, a benzyl ether moiety, a carbamate moiety, an ═NR14 moiety, and a carbonate moiety, wherein each of —(CH2)nC(O)R11, —(CH2)nC(O)2R11, —(CH2)nC(O)NR12R13, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl is optionally substituted with from 1 to 3 substituents independently selected at each occurrence thereof from C1-C3 alkyl, halogen, —CN, —OR12, —NR12R13, an amino acid group, and phenyl which is optionally substituted 1-3 times with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, —CN, —OR12, or —NR12R13; R4 is selected from the group consisting of H, halogen, —OR12, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —(CH2)nC(O)R11, —(CH2)nC(O)NR12R13, —(CH2)nOC(O)NR12R13, phenyl, benzyl, ═NOR14, ═NR14, a benzyl ether moiety, a carbamate moiety, an ═NR14 moiety, and a carbonate moiety, wherein each of —(CH2)nC(O)R11, —(CH2)nC(O)NR12R13, C1-C6 alkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, phenyl, and benzyl is optionally substituted with from 1 to 3 substituents independently selected at each occurrence thereof from C1-C3 alkyl, halogen, —CN, —OR12, —NR12R13, an amino acid group, and phenyl which is optionally substituted 1-3 times with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, —CN, —OR12, or —NR12R13; R5 is selected from the group consisting of H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —(CH2)nC(O)R11, —(CH2)nC(O)NR12R13, phenyl, benzyl, a benzyl ether moiety, a carbamate moiety, an ═NR14 moiety, and a carbonate moiety, wherein each of C1-C6 alkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —(CH2)nC(O)R11, —(CH2)nC(O)NR12R13, phenyl, and benzyl is optionally substituted 1 to 3 times with halogen, cyano, —NO2, —NR12R13, —OR12, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or an amino acid group; R6 is optionally present and, if present, is selected from the group consisting of H, —OR12, NR12R13, —(CH2)n(O)R11, —(CH2)nC(O)NR12R13, C1-C6 alkyl, C1-C6 haloalkyl, phenyl, benzyl, a benzyl ether moiety, a carbamate moiety, an ═NR14 moiety, and a carbonate moiety, wherein each of —(CH2)n(O)R11, —(CH2)nC(O)NR12R13, C1-C6 alkyl, C1-C6 haloalkyl, phenyl, and benzyl is optionally substituted 1 to 3 times with halogen, cyano, —NO2, —NR12R13, —OR12, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or an amino acid group; or R5 and R6 can combine to form a heterocycle group containing from 1 to 5 heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur and optionally substituted 1 to 3 times with halogen, oxo, cyano, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy; R7 is selected from the group consisting of H, halogen, —OR12, —NR12R13, —NR12C(O)R13, —NR12C(O)2R13, —NR12C(O)NR12R13, —S(O)qR12, —CN, —NO2, —(CH2)nC(O)R11, —(CH2)nC(O)2R11, —(CH2)nC(O)NR12R13, —(CH2)nOC(O)NR12R13, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, heterocyclyl, aryl, heteroaryl, a benzyl ether moiety, a carbamate moiety, an ═NR14 moiety, and a carbonate moiety, wherein each of —(CH2)nC(O)R11, —(CH2)nC(O)2R11, —(CH2)nC(O)NR12R13, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl is optionally substituted with from 1 to 3 substituents independently selected at each occurrence thereof from C1-C3 alkyl, halogen, —CN, —OR12, —NR12R13, an amino acid group, and phenyl which is optionally substituted 1-3 times with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, —CN, —OR12, or —NR12R13; R8 and R9 are each independently selected from the group consisting of H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —(CH2)nC(O)R11, —(CH2)nC(O)2R11, —(CH2)nC(O)NR12R13, —(CH2)nC(O)NR12R13, —OR12, phenyl, benzyl, a benzyl ether moiety, a carbamate moiety, and a carbonate moiety, wherein each of C1-C6 alkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —(CH2)nC(O)R11, —(CH2)nC(O)2R11, —(CH2)nC(O)NR12R13, phenyl, and benzyl is optionally substituted from 1 to 3 times with a substituent selected independently at each occurrence thereof from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and an amino acid group; or R8 and R9 can combine to form an oxo, thio, imine, or an ═NR14 moiety; R10 is optionally present and, if present, is selected from the group consisting of H, —OR12, (CH2)nC(O)R11, —(CH2)nC(O)NR12R13, C1-C6 alkyl, C1-C6 haloalkyl, benzyl, a carbohydrate, a benzyl ether moiety, a carbamate moiety, an ═NR14 moiety, and a carbonate moiety, wherein each of —(CH2)nC(O)R11, —(CH2)nC(O)NR12R13, C1-C6 alkyl, C1-C6 haloalkyl, and benzyl is optionally substituted 1 to 3 times with halogen, cyano, —NO2, —NR12R13, —OR12, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or an amino acid group; R11 is H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —C(O)R15, phenyl, or benzyl, wherein each of C1-C6 alkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, phenyl, and benzyl is optionally substituted 1 to 3 times with halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or an amino acid group; R12 and R13 are each independently selected from the group consisting of H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —(CH2)nNR16R17, —(CH2)nC(O)R11, —(CH2)nOC(O)R11, —(CH2)nC(O)2R11, —(CH2)nC(O)NR16R17, (CH2)nOC(O)NR16R17, —(CH2)nNR16C(O)OR17, —(CH2)nNC(O)NR16R17, aryl, heteroaryl, arylalkyl, and heteroarylalkyl, wherein each of C1-C6 alkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —(CH2)nNR16R17, —(CH2)nC(O)R11, —(CH2)nOC(O)R11, —(CH2)nC(O)2R11, —(CH2)nC(O)NR16R17, —(CH2)nOC(O)NR16R17, —(CH2)nNR16C(O)OR17, —(CH2)nNC(O)NR16R17, aryl, heteroaryl, arylalkyl, and heteroarylalkyl is optionally substituted 1 to 3 times with halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, OH, C1-C4 alkoxy, an amino acid group, or [NR11C(O)(CH2)n]mNR16R17, which is optionally substituted 1 to 3 times with halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy, aryl alkyl, wherein the C1-C4 alkyl and the aryl alkyl substituents are optionally substituted 1 to 3 times with halogen, alkyl, OH, NH2, —CO2H, —C(O)NH2, —NHC(O)NH2, —NHC(NH)NH2, imidazole, pyrrolidine, SMe, SH, or SeH; or R12 and R13 are taken together with the nitrogen to which they are attached to form a five- to seven-membered heterocyclic ring, which may be saturated or unsaturated and comprises from 1 to 2 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and is optionally substituted from 1 to 4 times with a substituent selected independently at each occurrence thereof from the group consisting of halogen, cyano, oxo, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy; R14 is selected from the group consisting of H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —S(O)qR12, —(CH2)nNR12R13, —(CH2)nC(O)R11, —(CH2)nOC(O)R11, —(CH2)nC(O)2R11, —(CH2)nC(O)NR12R13, —(CH2)nOC(O)NR12R13, (CH2)nNR11C(O)OR12, —(CH2)nNC(O)NR12R13, aryl, heteroaryl, arylalkyl, and heteroarylalkyl, wherein each of C1-C6 alkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —(CH2)nC(O)R11, —(CH2)nOC(O)R11, —(CH2)nC(O)2R11, —(CH2)nC(O)NR12R13, —(CH2)nOC(O)NR12R13, —(CH2)nNR11C(O)OR12, —(CH2)nNC(O)NR12R13, aryl, heteroaryl, arylalkyl, and heteroarylalkyl is optionally substituted with from 1 to 3 substituents independently selected at each occurrence thereof from C1-C3 alkyl, halogen, —CN, —OR12, —NR12R13, and phenyl which is optionally substituted 1-3 times with halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, —CN, —NO2, OR12, —NR12R13, or an amino acid group; R15 is H, C1-C4 alkyl, arylalkyl, heteroarylalkyl C1-C4 haloalkyl, or phenyl, wherein each of C1-C4 alkyl, arylalkyl, heteroarylalkyl C1-C4 haloalkyl, and phenyl is optionally substituted 1 to 3 times with halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, or an amino acid group; R16 and R17 are each independently H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, —C(O)R15, —C(O)OR15, phenyl, or benzyl, wherein each of C1-C6 alkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, phenyl, and benzyl is optionally substituted from 1 to 3 times with a substituent selected independently at each occurrence thereof from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and an amino acid group; or R16 and R17 are taken together with the nitrogen to which they are attached to form a five- to seven-membered heterocyclic ring, which may be saturated or unsaturated and comprises from 1 to 2 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and is optionally substituted from 1 to 4 times with a substituent selected independently at each occurrence thereof from the group consisting of halogen, cyano, oxo, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy; X is O or N; Y is O or N; m is 0, 1, 2, or 3; n is 0 to 5; q is 0, 1, or 2; and represents an optional double bond; with the provisos: (1) if R1 is H, R2 is OCH3, R3 is H, R4 is OH or H, R5 is H, R7 is H, R8 and R9 are combined to form an oxo, R10 is H, and X and Y are O, then at least one of R1 to R10 is a benzyl ether moiety, a carbamate moiety, an ═NR14 moiety, or a carbonate moiety; and (2) that X, R6, R8, and R9 can form a dihydroquinone ring; or a pharmaceutically acceptable salt thereof.
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