Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine
- 1 August 1989
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 32 (8), 1861-1865
- https://doi.org/10.1021/jm00128a029
Abstract
Both enantiomers of the carbocyclic analogues of 5-iodo-2''-deoxyuridine (14 and ent-14) and of (E)-5-(2-bromovinyl)-2''-deoxyuridine (16 and ent-16) were synthesized by using (+)- or (-)-endo-norborn-5-en-2-yl acetate or butyrate, respectively, as starting materials. Against herpes simplex virus type 1 (+)-C-BVDU (16) was only slightly less active than BVDU itself, whereas (-)-C-BVDU (ent-16) proved to be 10-400-fold less effective, depending on the strain investigated. Against HSV-2 both (+)- and (-)-C-BVDU as well as (+)- and (-)-C-IDU showed minor activity. All carbocyclic analogues were inactive against TK- HSV-1 strains, pointing to the prerequisite of phosphorylation (activation) by the viral thymidine kinase (TK).This publication has 4 references indexed in Scilit:
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