Prodigiosin analogs and methods of use

A method of preparing a compound of Formula XIV:

• wherein:
• R1 and R2 are, independently, selected from the group consisting of H, OH, halogen, —C1-6alkyl, —C1-6fluoroalkyl, —CN, —NO2, —OR7, —SR7, —S(═O)R7, —S(═O)2R7, —NHS(═O)2R7, —C(═O)R7, —OC(═O)R7, —CO2R7, —OCO2R7, —CH(R7)2, —N(R7)2, —C(═O)N(R7)2, —NHC(═O)NHR7,—NHC(═O)R7, —NHC(═O)OR7, —C(OH)(R7)2, and —C(NH2)(R7)2;
• each R7 is, independently, H, halogen, or C1-C6alkyl, wherein the alkyl group is optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halogen, OH, CN, and NO2;
• R3 is an optionally substituted aryl or an optionally substituted heteroaryl;
• R4, R5, and R6 are, independently, —OH, —C1-10alkyl, —OC1-10alkyl, or —SC1-10alkyl, wherein each alkyl group is, independently, optionally substituted by 1, 2, 3, 4, or 5 substituents independently selected from halogen, OH, CN, and NO2;
• and
• n is an integer from 0 to 5;
• wherein the method comprises:
• admixing a solvent, an acid, a compound of Formula XII
• and a compound of Formula XIII
• at a temperature sufficient to result in the formation of the compound of Formula XIV;
• the acid is selected from the group consisting of hydrochloric acid, hydrobromic acid, hydrofluoric acid, acetic acid, phosphoric acid, toluenesulfonic acid, sulfuric acid, and nitric acid;
• and
• the temperature is about from about 0° C. to about 100° C.