The 5-nitrofuran-2-ylmethylidene group as a potential bioreductively activated prodrug system for diol-containing drugs

Acid-catalysed condensation of 5-nitrofuran-2-carboxaldehyde with 1-phenyle thane-1,2-diol and with 2,2-dimethyl-1-phenylpropane-1,3-diol in boiling be nzene gave the expected cyclic nitrofuranyl acetals. Biomimetic reduction o f these acetals with sodium borohydride in the presence of palladium trigge red release of the parent diols. Thus these nitrofuran acetals may have pot ential for applications as prodrugs for selective release of diol-containin g drugs in hypoxic solid tumours.