THE SYNTHESIS AND ANTIVIRAL PROPERTIES OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE-RELATED COMPOUNDS

Article abstract of DOI:10.1016/S0040-4020(01)86902-7

A method for the synthesis of the potent anti-herpes agent, (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) (1) is described.A trace bye-product of the synthesis has been identified as 5-(1,2-dibromo-2-succinimidoethyl)-2'-deoxyuridine (5).A similar bye-product, 5-(1,2-dibromo-2-succinimidoethyl)uridine (4) is formed during the synthesis of (E)-5-(2-bromovinyl)uridine (3).The following derivatives of BVDU have been synthesised: 3'-O-methyl (8), 3-methyl (9), 4-O-ethyl (11), O²,5'-anhydro-(E)-5-(2-bromovinyl)-2'-deoxyuridine (13) and (E)-5-(2-bromovinyl)-2'-deoxyisocytidine (15).Whereas compounds 8, 9 and 15 showed little, if any, antiviral activity, 11 and, in particular, 13, were significantly active against herpes simplex virus type 1 and varicella-zoster virus.