Derivatives of xanthone compounds

A compound of Formula I or a salt thereof:

• wherein
• each of R1 and R2 are each independently is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, heteroaralkyl, —(C═O)R11, —(C═O)OR11, —(C═O)NR12R13, —SO2R11, —SO2NR12R13, or R14, wherein R14 is
• wherein
• n is 0-20;
• X is —O—, —(C═O)—, —O(C═O)—, —(C═O)O—, —N(R11)—, —(C═O)N(R11)—, —N(R11)(C═O)—, —O(C═O)N(R11)—, —N(R11)(C═O)O—, —N(R12)(C═O)N(R13)—, —NR11SO2—, or —SO2NR1—;
• each of R15, R16, R17, R18, R19, R20, R21, and R22 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkenyl, aralkyl, heteroaryl, heterocycloalkyl, heterocycloalkenyl, halide, cyano, nitro, isocyanate, —R14, —OR11, —SR11, —(C═O)R11, —(C═O)OR11, —O(C═O)R11, —O(C═O)OR11, —(C═O)NR12R13, —O(C═O)NR12R13, —NR12(C═O)OR13, —NR12R13, —N(R12)2R13, —N(R12)—NR12R13, —NR12(C═O)R13, —(S═O)R11, —SO2R11, —SO3R11, —OSO3R11, —OPO2OR11, —SO2NR12R13, —(C═NR12)NR12R13, —NR13(C═NR12)R11, or —N(R13)(C═NR12)NR12R13;
• or any two instances of R15, R16, R17, R18, R19, R20, R21, R22, or R23 taken together with the carbon to which they are bonded form (C═O);
• or any two instances of R15, R16, R17, R18, R19, R20, R21, R22, or R23 taken together with the carbon to which they are bonded form a 3-8 membered carbocylic or heterocyclic ring;
• or any two instances of R15, R16, R17, R18, R19, R20, R21, R22, or R23 taken together form a bond;
• R23 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heteroaryl, heterocycloalkyl, heterocycloalkenyl, halide, cyano, nitro, isocyanate, —R14, —OR11, —SR11, —(C═O)R11, —(C═O)OR11, —O(C═O)R11, —O(C═O)OR11, —(C═O)NR12R13, —O(C═O)NR12R13, —NR12(C═O)OR13, —NR12R13, —N(R12)2R13, —N(R12)—NR12R13, —NR12(C═O)R13, —(S═O)R11, —SO2R11, —SO3R11, —OSO3R11, —OPO2OR11, —PO2OR11, —SO2NR12R13, —(C═NR12)NR12R13, —NR13(C═NR12)R11, —NR11(C═NR12)R13, —N(R13)(C═NR12)NR12R13,
• OPO2OH, —OSO3H,
• each of R3 and R10 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, heteroaralkyl, —O(C═O)R11, —O(C═O)OR11, —O(C═O)NR12R13, —OSO3R11, or —OPO2OR11;
• each of R4 and R5 independently is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, heteroaralkyl, —OR11, —O(C═O)R11, —O(C═O)OR11, or —O(C═O)NR12R13;
• or R4 and R5 taken together with the carbon to which they are bonded form (C═O);
• each of R6, R7, R8, and R9 independently for each occurrence is hydrogen;
• or R6 and R7 taken together form a bond;
• or R8 and R9 taken together form a bond;
• R11 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, heteroaralkyl, or R14;
• and
• each of R12 and R13 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, heteroaralkyl, or R14;
• or R12 or R13 taken together form a 3-8 membered heterocyclic ring, wherein at least one of R1 or R2 is R14.

A compound of Formula II or a salt thereof:

• wherein
• m is 0-10;
• Y is O or H2;
• B is OH, OR11, or NR11R24;
• each of R3 and R10 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, heteroaralkyl, —O(C═O)R11, —O(C═O)OR11, —O(C═O)NR12R13, —OSO3R11, or —OPO2OR11;
• each of R4 and R5 is independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, heteroaralkyl, —OR11, —O(C═O)R11, —O(C═O)OR11, or —O(C═O)NR12R13;
• or R4 and R5 taken together with the carbon to which they are bonded form (C═O);
• each of R6, R7, R8, and R9 independently for each occurrence is hydrogen;
• or R6 and R7 taken together form a bond;
• or R8 and R9 taken together form a bond;
• R11 is independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, or heteroaralkyl;
• or R11 and R24 taken together with the nitrogen to which they are attached form a 3-8 membered heterocyclic ring;
• each of R12 and R13 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, or heteroaralkyl;
• or R12 or R13 taken together form a 3-8 membered heterocyclic ring;
• R24 is
• wherein
• n is 0-12;
• X is —O—, —(C═O)—, —O(C═O)—, —(C═O)O—, —N(R11)—, —(C═O)N(R11)—, —N(R11)(C═O)—, —O(C═O)N(R11)—, —N(R11)(C═O)O—, —N(R12)(C═O)N(R13)—, —NR11SO2—, or —SO2NR11—;
• each of R15, R16, R17, R18, R19, R20, R21, and R22 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heteroaryl, heterocycloalkyl, heterocycloalkenyl, halide, cyano, nitro, isocyanate, —R24, —OR11, —SR11, —(C═O)R11, —(C═O)OR11, —O(C═O)R11, —O(C═O)OR11, —(C═O)NR12R13, —O(C═O)NR12R13, —NR12(C═O)OR13, —NR12R13, —N(R12)2R13, —N(R12)—NR12R13, —NR12(C═O)R13, —(S═O)R11, —SO2R11, —SO3R11, —OSO3R11, —OPO2OR11, —PO2OR11, —SO2NR12R13, —(C═NR12)NR12R13, —NR13(C═NR12)R11, —NR11(C═NR12)R13, or —N(R13)(C═NR12)NR12R13;
• or any two instances of R15, R16, R17, R18, R19, R20, R21, R22, or R23 taken together with the carbon to which they are bonded form (C═O);
• or any two instances of R15, R16, R17, R18, R19, R20, R21, R22, or R23 taken together with the carbon to which they are bonded form a 3-8 membered carbocylic or heterocyclic ring;
• or any two instances of R15, R16, R17, R18, R19, R20, R21, R22, or R23 taken together form a bond;
• and
• R23 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heteroaryl, heterocycloalkyl, heterocycloalkenyl, halide, cyano, nitro, isocyanate, an amino acid, a dipeptide, a tripeptide, an oligopeptide, —R24, —OR11, —SR11, —(C═O)R11, —(C═O)OR11, —O(C═O)R11, —O(C═O)OR11, —(C═O)NR12R13, —O(C═O)NR12R13, —NR12(C═O)OR13, —NR12R13, —N(R12)2R13, —N(R12)—NR12R13, —NR12(C═O)R13, —(S═O)R11, —SO2R11, —SO3R11, —OSO3R11, —OPO2OR11, —PO2OR11, —SO2NR12R13, —(C═NR12)NR12R13, —NR13(C═NR12)R11, —NR11(C═NR12)R13, —N(R13)(C═NR12)NR12R13,

A compound of Formula III or a salt thereof:

• wherein
• m is 1-10;
• each of R3 and R10 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, heteroaralkyl, —O(C═O)R11, —O(C═O)OR11, —O(C═O)NR12R13, —OSO3R11, or —OPO2OR11;
• R4 and R5 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, heteroaralkyl, —OR11, —O(C═O)R11, —O(C═O)OR11, and —O(C═O)NR12R13;
• or R4 and R5 taken together with the carbon to which they are bonded form (C═O);
• each of R6, R7, R8, and R9 independently for each occurrence is hydrogen;
• or R6 and R7 taken together form a bond;
• or R8 and R9 taken together form a bond;
• R11 is independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, heteroaralkyl;
• or R11 and R24 taken together with the nitrogen to which they are attached form a 3-8 membered heterocyclic ring;
• each of R12 and R13 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heterocycloalkyl, heterocycloalkenyl, heteroaryl, or heteroaralkyl;
• or R12 or R13 taken together form a 3-8 membered heterocyclic ring;
• R24 is
• wherein
• n is 0-12;
• X is —O—, —(C═O)—, —O(C═O)—, —(C═O)O—, —N(R11)—, —(C═O)N(R11)—, —N(R11)(C═O)—, —O(C═O)N(R11)—, —N(R11)(C═O)O—, —N(R12)(C═O)N(R13)—, —NR11SO2—, or —SO2NR11—;
• each of R15, R16, R17, R18, R19, R20, R21, and R22 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heteroaryl, heterocycloalkyl, heterocycloalkenyl, halide, cyano, nitro, isocyanate, —R24, —OR11, —SR11, —(C═O)R11, —(C═O)OR11, —O(C═O)R11, —O(C═O)OR11, —(C═O)NR12R13, —O(C═O)NR12R13, —NR12(C═O)OR13, —NR12R13, —N(R12)2R13, —N(R12)—NR12R13, —NR12(C═O)R13, —(S═O)R11, —SO2R11, —SO3R11, —OSO3R11, —OPO2OR11, —PO2OR11, —SO2NR12R13, —(C═NR12)NR12R13, —NR13(C═NR12)R11, —NR11(C═NR12)R13, or —N(R13)(C═NR12)NR12R13;
• or any two instances of R15, R16, R17, R18, R19, R20, R21, R22, or R23 taken together with the carbon to which they are bonded form (C═O);
• or any two instances of R15, R16, R17, R18, R19, R20, R21, R22, or R23 taken together with the carbon to which they are bonded form a 3-8 membered carbocylic or heterocyclic ring;
• or any two instances of R15, R16, R17, R18, R19, R20, R21, R22, or R23 taken together form a bond;
• R23 independently for each occurrence is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, heteroaryl, heterocycloalkyl, heterocycloalkenyl, halide, cyano, nitro, isocyanate, —R14, —OR11, —SR11, —(C═O)R11, —(C═O)OR11, —O(C═O)R11, —O(C═O)OR11, —(C═O)NR12R13, —O(C═O)NR12R13, —NR12(C═O)OR13, —NR12R13, —N(R12)2R13, —N(R12)—NR12R13, —NR12(C═O)R13, —(S═O)R11, —SO2R11, —SO3R11, —OSO3R11, —OPO2OR11, —SO2NR12R13, —(C═NR12)NR12R13, —NR13(C═NR12)R11,