Preparation and evaluation of sulfide derivatives of the antibiotic brefeldin a as potential prodrug candidates with enhanced aqueous solubilities.

Several sulfide (+)-brefeldin A (BFA) analogues were prepared through the Michael addition of various thiols. Many of the sulfides were also oxidized to the corresponding sulfoxide with m-CPBA. The sulfides were designed to act as BFA prodrugs via the metabolic oxidation to the sulfoxide and subsequent syn elimination. Kinetic experiments were used to prove… CONTINUE READING