Synthesis and antiviral properties of (Z)-5-(2-bromovinyl)-2'-deoxyuridine

Abstract

(Z)-5-(2-Bromovinyl)uracil was obtained by photoisomerization of the E isomer; (E)-5-(2-bromovinyl)-2''-deoxyuridine gave the required Z isomer. (Z)-5-(2-Bromovinyl)-2''-deoxyuridine is much less active against herpes simplex virus type 1 (HSV-1) and somewhat less active against herpes simplex virus type 2 than is the E isomer. Both isomers show similar activity against vaccinia virus. The highly potent and selective activity of (E)-5-(2-bromovinyl)-2''-deoxyuridine against HSV-1 is due to its E configuration.