<i>E</i>-5-(2-Chlorovinyl)-2′-Deoxycytidine: Synthesis and Antiherpetic Activity

E-5-(2-chlorovinyl)-2′-deoxycytidine (CVDC) has been prepared for the first time using an improved synthesis of the starting material E-5-(2-chlorovinyl)-2′-deoxyuridine (CVDU). CVDC and CVDU were only slightly less active against herpes simplex virus type 1 (HSV-1) and varicella-zoster virus (VZV) than the potent anti-herpes compound E-5-(2-bromovinyl)-2′-deoxyuridine (BVDU). The Z-forms of CVDC and CVDU were markedly less active against HSV-1 and VZV than the E-isomers. None of the compounds showed activity against thymidine kinase (TK)-deficient variants of HSV-1.