Journal of Medicinal Chemistry 1981-06-01

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

A S Jones, S G Rahim, R T Walker, E De Clercq

Index: J. Med. Chem. 24(6) , 759-60, (1981)

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Abstract

(Z)-5-(2-Bromovinyl)uracil was obtained by photoisomerization of the E. isomer. Similarly, (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. Therefore, the highly potent and selective activity of (E)-5-(2-bromovinyl)-2'-deoxyuridine against HSV-1 is due to its E configuration.