The synthesis of water soluble prodrugs analogs of echinocandin B

A facile synthesis of phosphonate and phosphate ester prodrugs on the phenolic hydroxy of two echinocandin semisynthetic derivatives is reported. The water solubility and stability profiles of the ECB compounds varied with the choice of alkyl group used. In some cases, the ester prodrugs with small aliphatic side chains retained antifungal activity while enhancing water solubility. A facile synthesis of phosphonate and phosphate ester prodrugs on the phenolic hydroxy of two echinocandin semisynthetic derivatives is reported. The water solubility and stability profiles of the ECB compounds varied with the choice of alkyl group used. In some cases, the ester prodrugs with small aliphatic side chains retained antifungal activity while enhancing water solubility.