Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine
| Autor: | Herfried Griengl, Michael Bodenteich, Jan Balzarini, Harald Baumgartner, Erik De Clercq |
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| Rok vydání: | 1989 |
| Předmět: |
Chemical Phenomena
Chemistry Stereochemistry Stereoisomerism Cyclopentanes Microbial Sensitivity Tests Butyrate medicine.disease_cause Antiviral Agents Deoxyuridine chemistry.chemical_compound Herpes simplex virus Bromodeoxyuridine Thymidine kinase Drug Discovery medicine Simplexvirus Molecular Medicine Phosphorylation Enantiomer |
| Zdroj: | Journal of Medicinal Chemistry. 32:1861-1865 |
| ISSN: | 1520-4804 0022-2623 |
| DOI: | 10.1021/jm00128a029 |
| Popis: | Both enantiomers of the carbocyclic analogues of 5-iodo-2'-deoxyuridine (14 and ent-14) and of (E)-5-(2-bromo-vinyl)-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). |
| Databáze: | OpenAIRE |
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