Nicotinamide riboside and analogues thereof

A method for promoting survival of a eukaryotic cell comprising contacting the cell with at least one compound of Structural Formula (III) or (IV):

• or a pharmaceutically acceptable salt thereof, wherein:
• R201 and R202 are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted non-aromatic heterocyclic group or a substituted or unsubstituted aryl group, or R201 and R202 taken together with the atom to which they are attached form a substituted or unsubstituted non-aromatic heterocyclic group;
• R203, R204, R205 and R206 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R207, R208 and R210 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR;
• R209 is selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′ and —NRC(O)R′;
• R211, R212, R213 and R214 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R and R′ are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted non-aromatic heterocyclic group;
• X is O or S;
• and
• n is 1 or 2.

A method for treating or preventing a disease or disorder associated with cell death, cell dysfunction or aging in a subject, comprising administering to a subject in need thereof a therapeutically effective amount of at least one compound of Structural Formula (III) or (IV):

• or a pharmaceutically acceptable salt thereof, wherein:
• R201 and R202 are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted non-aromatic heterocyclic group or a substituted or unsubstituted aryl group, or R201 and R202 taken together with the atom to which they are attached form a substituted or unsubstituted non-aromatic heterocyclic group;
• R203, R204, R205 and R206 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R207, R208 and R210 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR;
• R209 is selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′ and —NRC(O)R′;
• R211, R212, R213 and R214 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R and R′ are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted non-aromatic heterocyclic group;
• X is O or S;
• and
• n is 1 or 2.

A method for treating or preventing insulin resistance, a metabolic syndrome, artherogenic dyslipidemia, hypercholesterolemia, diabetes, or complications thereof, or for increasing insulin sensitivity in a subject, comprising administering to a subject in need thereof a therapeutically effective amount of at least one compound of Structural Formula (III) or (IV):

• or a pharmaceutically acceptable salt thereof, wherein:
• R201 and R202 are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted non-aromatic heterocyclic group or a substituted or unsubstituted aryl group, or R201 and R202 taken together with the atom to which they are attached form a substituted or unsubstituted non-aromatic heterocyclic group;
• R203, R204, R205 and R206 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R207, R208 and R210 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR;
• R209 is selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′ and —NRC(O)R′;
• R211, R212, R213 and R214 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R and R′ are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted non-aromatic heterocyclic group;
• X is O or S;
• and
• n is 1 or 2,
• provided that when X is O and R201-R209 and R211-R214 are —H, R210 is not —H.

A method for reducing the weight of a subject, or preventing weight gain in a subject, comprising administering to a subject in need thereof a therapeutically effective amount of at least one compound of Structural Formula (III) or (IV):

• or a pharmaceutically acceptable salt thereof, wherein:
• R201 and R202 are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted non-aromatic heterocyclic group or a substituted or unsubstituted aryl group, or R201 and R202 taken together with the atom to which they are attached form a substituted or unsubstituted non-aromatic heterocyclic group;
• R203, R204, R205 and R206 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R207, R208 and R210 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR;
• R209 is selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′ and —NRC(O)R′;
• R211, R212, R213 and R214 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R and R′ are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted non-aromatic heterocyclic group;
• X is O or S;
• and
• n is 1 or 2.

A method for prolonging the lifespan of a subject comprising administering to a subject a therapeutically effective amount of at least one compound of Structural Formula (III) or (IV):

• or a pharmaceutically acceptable salt thereof, wherein:
• R201 and R202 are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted non-aromatic heterocyclic group or a substituted or unsubstituted aryl group, or R201 and R202 taken together with the atom to which they are attached form a substituted or unsubstituted non-aromatic heterocyclic group;
• R203, R204, R205 and R206 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R207, R208 and R210 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR;
• R209 is selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′ and —NRC(O)R′;
• R211, R212, R213 and R214 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R and R′ are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted non-aromatic heterocyclic group;
• X is O or S;
• and
• n is 1 or 2.

A method for treating or preventing a neurodegenerative disorder in a subject, comprising administering to a subject in need thereof a therapeutically effective amount of at least one compound of Structural Formula (III) or (IV):

• or a pharmaceutically acceptable salt thereof, wherein:
• R201 and R202 are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted non-aromatic heterocyclic group or a substituted or unsubstituted aryl group, or R201 and R202 taken together with the atom to which they are attached form a substituted or unsubstituted non-aromatic heterocyclic group;
• R203, R204, R205 and R206 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R207, R208 and R210 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR;
• R209 is selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′ and —NRC(O)R′;
• R211, R212, R213 and R214 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R and R′ are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted non-aromatic heterocyclic group;
• X is O or S;
• and
• n is 1 or 2.

A method for treating or preventing a blood coagulation disorder in a subject, comprising administering to a subject in need thereof a therapeutically effective amount of at least one compound of Structural Formula (III) or (IV):

• or a pharmaceutically acceptable salt thereof, wherein:
• R201 and R202 are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted non-aromatic heterocyclic group or a substituted or unsubstituted aryl group, or R201 and R202 taken together with the atom to which they are attached form a substituted or unsubstituted non-aromatic heterocyclic group;
• R203, R204, R205 and R206 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R207, R208 and R210 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR;
• R209 is selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′ and —NRC(O)R′;
• R211, R212, R213 and R214 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R and R′ are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted non-aromatic heterocyclic group;
• X is O or S;
• and
• n is 1 or 2.

A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and a compound represented by Structural Formula (V) or (VI):

• or a pharmaceutically acceptable salt thereof, wherein:
• R1 and R2 are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted non-aromatic heterocyclic group or a substituted or unsubstituted aryl group, or R1 and R2 taken together with the atom to which they are attached form a substituted or unsubstituted non-aromatic heterocyclic group, provided that when one of R1 and R2 is —H, the other is not an alkyl group substituted by —C(O)OCH2CH3;
• R3, R4 and R5 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R6 is selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R7, R8 and R10 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR;
• R9 selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′ and —NRC(O)R′;
• R11, R12, R13 and R14 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R and R′ are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted non-aromatic heterocyclic group;
• X is O or S;
• and
• n is 1 or 2,
• provided that R1-R14 are not each —H and that R1-R9 and R11-R14 are not each —H when R10 is —C(O)C6H5.

A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and a compound represented by Structural Formula (IX) or (X):

• or a pharmaceutically acceptable salt thereof, wherein:
• R101 and R102 are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted non-aromatic heterocyclic group or a substituted or unsubstituted aryl group, or R101 and R102 taken together with the atom to which they are attached form a substituted or unsubstituted non-aromatic heterocyclic group;
• R103, R104, R105 and R106 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R107 and R108 are selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR, wherein at least one of R107 and R108 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR or —C(O)SR;
• R109 is selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′ and —NRC(O)R′;
• R110 is selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR, provided that R110 is not —C(O)C6H5;
• R111, R112, R113 and R114 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R and R′ are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted non-aromatic heterocyclic group;
• X is O or S;
• and
• n is 1 or 2.

A compound represented by Structural Formula (XI) or (XII):

• or a pharmaceutically acceptable salt thereof, wherein:
• R1 and R2 are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted non-aromatic heterocyclic group or a substituted or unsubstituted aryl group, or R1 and R2 taken together with the atom to which they are attached form a substituted or unsubstituted non-aromatic heterocyclic group;
• R3, R4, R5 and R6 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R7, R8 and R10 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR, wherein at least one of R7 and R8 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR or —C(O)SR, provided that none of R7 and R8 are —C(O)C6H5 and that R7 and R8 are not both —C(O)CH3 or —C(O)C6H4F;
• R9 selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′ and —NRC(O)R′;
• R11, R12, R13 and R14 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R and R′ are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted non-aromatic heterocyclic group;
• X is O or S;
• and
• n is 1 or 2.

A compound represented by Structural Formula (XI) or (XII):

• or a pharmaceutically acceptable salt thereof, wherein:
• R1 and R2 are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted non-aromatic heterocyclic group or a substituted or unsubstituted aryl group, or R1 and R2 taken together with the atom to which they are attached form a substituted or unsubstituted non-aromatic heterocyclic group;
• R3, R4, R5 and R6 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R7 and R8 are selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR;
• R9 selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —OR, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —SR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′ and —NRC(O)R′;
• R10 is selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, —C(O)R, —C(O)OR, —C(O)NHR, —C(S)R, —C(S)OR and —C(O)SR, provided that R10 is not —C(C6H5)3, —C(O)C6H5, —C(O)CH3, —C(O)C6H4F or —C(O)CH(OC(O)CH3)CH(CH3)CH2CH3;
• R11, R12, R13 and R14 are independently selected from the group consisting of —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted non-aromatic heterocyclic group, halogen, —CN, —CO2R, —OCOR, —OCO2R, —C(O)NRR′, —OC(O)NRR′, —C(O)R, —COR, —OSO3H, —S(O)nR, —S(O)nOR, —S(O)nNRR′, —NRR′, —NRC(O)OR′, —NO2 and —NRC(O)R′;
• R and R′ are independently —H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted non-aromatic heterocyclic group;
• X is O or S;
• and
• n is 1 or 2.