1-Glyoxlylamide indolizines for treating cancer

A method of treating a subject with cancer comprising administering to the subject an effective amount of a compound represented by the following structural formula:

• 63
• or a pharmaceutically acceptable salts thereof, wherein:
• Ring A is substituted or unsubstituted and is optionally fused to an aryl group;
• Z1 and Z2 are independently ═O, ═S, ═N—OR12 or ═NR12.
• R1 and R2 are independently —H, an aliphatic group, a substituted aliphatic group, an unsubstituted non-aromatic heterocylic group, a substituted non-aromatic heterocylic group, an unsubstituted aryl group or a substituted aryl group, provided that R1 and R2 are not both —H;
• or —NR1R2, taken together, is a substituted or unsubstituted non-aromatic nitrogen-containing heterocyclic group or a substituted or unsubstituted nitrogen-containing heteroaryl group;
• R3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted aliphatic group;
• X is a covalent bond, —C(R4R5)—, —N(R4)—, —O—, —S—, —S(O)—, —S(O)2—, —C(═O)—, —C(═O)—N(R4)—, or —N(R4)—C(═O)—;
• R4 and R5 are independently —H or a substituted or unsubstituted aliphatic group;
• and
• R12 is —H or a substituted or unsubstituted alkyl group.

A method of preparing a product compound represented by the following structural formula:

• 72
• said method comprising the step of reacting a CuI salt with a precursor compound represented by the following structural formula:
• 73
• wherein:
• Ring A is substituted or unsubstituted and optionally fused to an aryl group;
• R3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted aliphatic group;
• X is a covalent bond, —C(R4R5)—, —N(R4)—, —O—, —S—, —S(O)—, —S(O)2—, —C(═O)—, —C(═O)—N(R4)—, or —N(R4)—C(═O)—, provided that when X is —C(R4R5)—, then R3 is not a substituted or unsubstituted aliphatic group;
• and
• R4 and R5 are independently —H or a substituted or unsubstituted aliphatic group.

A method of preparing a product compound represented by the following structural formula:

• 80
• said method comprising the step of reacting a CuI salt with a precursor compound represented by the following structural formula:
• 81
• wherein R11 is —CH3, —CH2CH3, —OCH3, —F, —Cl or —CN.