Synthesis and Antiviral Activity of the Carbocyclic Analogues of (E)-5-(2-Halovinyl)-2'-deoxyuridines and (E)-5-(2-Halovinyl)-2'-deoxycytidines

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Abstract
The carbocyclic analogs of the potent and selective antiherpes agents (E)-5-(2-bromovinyl)-2''-deoxyuridine (BVDU), (E)-5-(2-iodovinyl)-2''-deoxyuridine (IVDU) and (E)-5-(2-bromovinyl)-2''-deoxycytidine (BVDC) were synthesized by conventional methods with use of carbocyclic 2''-deoxyuridine as starting material. C-BVDU, C-IVDU, and C-BVDC were equally selective, albeit slightly less potent, in their antiherpes action than BVDU, IVDU, and BVDC. Although resistant to degradation by pyrimidine nucleoside phosphorylases, C-BVDU did not prove more effective than BVDU in the systemic (oral, i.p.) or topical treatment of HSV-1 [herpes simplex I virus] infections in mice.

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