Tetrahedron p. 4601 - 4608 (1987)
Update date:2022-08-05
Topics:
Ashwell, Mark
Jones, A. Stanley
Kumar, Ajit
Sayers, Jon R.
Walker, Richard T.
et. al.
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.
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