83967-03-7Relevant academic research and scientific papers
Synthesis and antiviral activity of the carbocyclic analogue of the highly potent and selective anti-VZV bicyclo furano pyrimidines
Migliore, Marco D.,Zonta, Nicola,McGuigan, Christopher,Henson, Geoffrey,Andrei, Graciela,Snoeck, Robert,Balzarini, Jan
, p. 6485 - 6492 (2008/03/27)
Carbocyclic nucleoside analogues are catabolically stable since they are resistant to phosphorolytic cleavage by pyrimidine nucleoside phosphorylase enzymes. The carbocyclic analogue (C-BCNA) of the highly potent and selective anti-VZV bicyclic nucleoside
Synthesis and Antiviral Activity of the Carbocyclic Analogues of (E)-5-(2-Halovinyl)-2'-deoxyuridines and (E)-5-(2-Halovinyl)-2'-deoxycytidines
Herdewijn, Piet,Clercq, Erik De,Balzarini, Jan,Vanderhaeghe, Hubert
, p. 550 - 555 (2007/10/02)
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.
Carbocyclic analogues of 5-substituted uracil nucleosides: Synthesis and antiviral activity
Shealy,O'Dell,Shannon,Arnett
, p. 156 - 161 (2007/10/02)
Carbocyclic analogues of 3'-deoxyuridines and uridines with substituents at position 5 of the uracil moiety were prepared by direct halogenation (5-bromo and 5-iodo groups) and by displacement of the 5-bromo group by amino and substituted-amino groups. The analogue of 5-(hydroxymethyl)uridine was prepared via reaction of the isopropylidene derivative of the uridine analogue with paraformaldehyde. The carbocyclic analogues of thymidine and of 5-bromo-, 5-iodo-, and 5-(methylamino)-2'-deoxyuridine were highly active in vitro against herpes simplex virus, types 1 and 2. The corresponding analogues of 5-substituted 3'-deoxyuridines and of 5-substituted uridines were not active in this assay.
