Thiohydroxamates as inhibitors of histone deacetylase

A 1,3-disubstituted-1H-indole-6-thiohydroxamic acid compound, wherein the substituent at the 1-position is —X2—R2 and the substituent at the 3-position is R3, wherein:

• X2 is a bond, or a substituted or unsubstituted group selected from among C1-C6alkylene, C2-C6alkenylene, C2-C6 alkynylene, C1-C6-fluoroalkylene, C2-C6-fluoroalkenylene, C1-C6haloalkylene, C2-C6haloalkenylene, C1-C6heteroalkylene;
• C(═O)—, and C(═O)—C1-C6alkylene;
• R2 is a substituted or unsubstituted group selected from among aryl, heteroaryl, cycloalkyl, and heterocycloalkyl;
• where if R2 is substituted, then each substituent on R2 is selected from among hydrogen, halogen, —CN, —NO2, —S(═O)2NH2, —CO2H, —CO2R10, —C(═O)R11, —S—R11, —S(═O)—R11, —S(═O)2—R11, —NR10C(═O)—R11, —C(═O)N(R10)2, —S(═O)2N(R10)2, —NR10S(═O)2—R11, —OC(═O)N(R10)2, —NR10C(═O)O—R11, —OC(═O)O—R11, —NHC(═O)NH—R11, —OC(═O)—R11;
• —N(R10)2, substituted or unsubstituted C1-C6alkyl, C1-C6-fluoroalkyl, substituted or unsubstituted C2-C6alkenyl, substituted or unsubstituted C2-C6alkynyl, substituted or unsubstituted C1-C6alkoxy, C1-C6 fluoroalkoxy, substituted or unsubstituted C1-C6heteroalkyl, substituted or unsubstituted C3-C8cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
• R10 is hydrogen, or a substituted or unsubstituted group selected from among C1-C6alkyl, C1-C6fluoroalkyl, C1-C6heteroalkyl, C3-C8cycloalkyl, C2-C8heterocycloalkyl, aryl, and heteroaryl;
• R11 is a substituted or unsubstituted group selected from among C1-C6alkyl, C1-C6fluoroalkyl, C3-C8cycloalkyl, C2-C8heterocycloalkyl, aryl, and heteroaryl;
• R3 is hydrogen, halogen, substituted or unsubstituted C1-C6alkyl, substituted or unsubstituted C2-C6alkenyl, substituted or unsubstituted C2-C6alkynyl, substituted or unsubstituted C1-C6alkoxy, substituted or unsubstituted C1-C6fluoroalkoxy, substituted or unsubstituted C1-C6heteroalkyl, substituted or unsubstituted phenyl, or —X6—R6;
• X6 is a C1-C6alkylene, C1-C6fluoroalkylene, C2-C6alkenylene, C2-C6heteroalkylene;
• R6 is hydrogen, halogen, —CN, hydroxy, amino, C1-C6alkylamino, di(C1-C6alkyl)amino, C1-C6alkoxy, C3-C8cycloalkyl, C2-C8heterocycloalkyl, phenyl, heteroaryl, or X7—R7
• X7 is a bond, —O—, —S—, —S(═O)—, —S(═O)2—, —NRa—, —C(═O)—, —C(═O)O—, —OC(═O)—, —NHC(═O)—, —C(═O)NRa—, —S(═O)2NRa—, —NHS(═O)2—, —OC(═O)NRa—, —NHC(═O)O—, —OC(═O)O—, —NHC(═O)NRa—;
• R7 is hydrogen, C1-C6alkyl, C2-C6alkenyl, C1-C6heteroalkyl, C1-C6haloalkyl, C3-C8cycloalkyl, cycloalkylalkyl, C2-C8heterocycloalkyl, heterocycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl,
• Ra is selected from among hydrogen, C1-C6alkyl, C2-C6alkenyl, hydroxy, C1-C6alkoxy, C1-C6fluoroalkoxy, C1-C6heteroalkyl;
• or
• Ra and R7 together with the N atom to which they are attached form a 5-, 6-, or 7-membered heterocycloalkyl;
• or an active metabolite, pharmaceutically acceptable solvate, pharmaceutically acceptable salt, pharmaceutically acceptable N-oxide, or pharmaceutically acceptable prodrug thereof.