Curcuminoids, analogs thereof, and methods of making the same

A method of making a compound, the method comprising:

• combining
• acetylacetone, 2-acetylcylohexanone, 2-acetylcyclopentanone, or 2-acetylcyclohexane-1,3-dione,
• an aldehyde having the structure X—C(O)H and/or Y—C(O)H,
• B2O3,
• RB—NH2, and
• (RBO)3B, wherein RB is independently (C1-C10) alkyl, to form the compound, wherein the compound has the structure:
• wherein
• A is —C—,
• X and Y are independently chosen from
• substituted or unsubstituted aryl, and
• substituted or unsubstituted heteroaryl;
• and
• wherein
• X and Y have different structures, or
• X and Y are independently chosen from 2- nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-cholorophenyl, 3-cholorophenyl, 4-cholorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 3,5-dimethoxyphenyl, 4-(trifluoromethyl)phenyl, 2-naphthyl, 6-methoxy-2-naphthyl, 3-methoxy-4hydroxyphenyl, 2-hydroxy-3-methoxyphenyl, 4- cyanophenyl,
• the compound has the structure:

A compound having the structure:

• wherein
• A is —C—,
• X and Y are independently chosen from
• substituted or unsubstituted aryl, and
• substituted or unsubstituted heteroaryl,
• wherein X and Y have different structures, and
• L is a substituted or unsubstituted linker group chosen form —(CH2)3, —(CH2)2—, and —CH2—CH2—C(O)—.

A method of killing a microbe or decreasing the rate of proliferation of a microbe, the method comprising:

• contacting the microbe and a compound having the structure:
• wherein
• A is —C—,
• X and Y are independently chosen from
• substituted or unsubstituted aryl, and
• substituted or unsubstituted heteroaryl, and
• L is a substituted or unsubstituted linker group chosen from —(CH2)3—, —(CH2)2—, and —CH2—CH2—C(O)—.