Synthesis and Antiviral Activity of (E)-5-(2-Bromovinyl)uracil and (E)-5-(2-Bromovinyl)uridine

Article abstract of DOI:10.1021/jm00152a008

(E)-5-(2-Bromovinyl)uracil (BVU) and (E)-5-(2-bromovinyl)uridine (BVRU) were synthesized starting from 5-formyluracil via (E)-5-(2-carboxyvinyl)uracil or starting from 5-iodouridine via (E)-5-(2-carbomethoxyvinyl)uridine and (E)-5-(2-carboxyvinyl)uridine, respectively.Depending on the choice of the cell system, BVU and BVRU exhibited a marked activity against herpes simplex virus type 1 (HSV-1) in vitro.Although BVU and BVRU were less potent than the reference compound (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU), their antiviral activity spectrum was remarkably similar to that of BVDU.The latter findings suggest that BVU and BVRU are metabolically converted to BVDU or a phosphorylated product thereof.In vivo, BVU protected mice against a lethal disseminated HSV-1 infection.