Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines.

Abstract

The carbocyclic analogues 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, intraperitoneal) or topical treatment of HSV-1 infections in mice.

• Authors: P Herdewijn, E De Clercq, J Balzarini, H Vanderhaeghe
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 28 Issue 5 Pg. 550-5 (May 1985) ISSN: 0022-2623 [Print] United States
• PMID: 2985782 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Antiviral Agents
• Cyclopentanes
• Deoxycytidine
• brivudine
• 1-(3-hydroxy-4-(hydroxymethyl)-cyclopentyl)-5-(2-bromovinyl)-2,4-(1H,3H)-pyrimidinedione
• 1-(3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-(2-iodovinyl)-2,4-(1H,3H)-pyrimidinedione
• 1-((3-hydroxy)-4-(hydroxymethyl)cyclopentyl)-4-amino-5-(2-bromovinyl)-2(1H)-pyrimidinone
• Bromodeoxyuridine
• Deoxyuridine

Topics

• Animals
• Antineoplastic Agents (chemical synthesis)
• Antiviral Agents (chemical synthesis, therapeutic use)
• Bromodeoxyuridine (analogs & derivatives, pharmacology)
• Cell Division (drug effects)
• Cell Line
• Cyclopentanes (chemical synthesis, pharmacology, therapeutic use)
• Cytopathogenic Effect, Viral (drug effects)
• Deoxycytidine (analogs & derivatives, chemical synthesis, pharmacology)
• Deoxyuridine (analogs & derivatives, chemical synthesis, pharmacology, therapeutic use)
• Herpes Simplex (drug therapy)
• Humans
• Mice
• Mice, Hairless
• Rabbits
• Rats
• Simplexvirus (drug effects)
• Vaccinia virus (drug effects)
• Vesicular stomatitis Indiana virus (drug effects)
• Virus Cultivation