91661-22-2Relevant academic research and scientific papers
Synthesis of the Carbocyclic Analogue of the Antiviral Nucleoside (E)-5-(2-Bromovinyl)-2'-deoxyuridine
Cookson, Richard C.,Dudfield, Philip J.,Scopes, David I.C.
, p. 399 - 404 (2007/10/02)
The cyclopentanecarboxylic acid (1) was converted via the isocyanate (2) and the urea (5) into carbocyclic uridine (12).Similarly, the α- and β-epimers of carbocyclic 2'-deoxyuridine, (19a) and (19b), were synthesized from the acids (13).Compounds (19a) and (19b) were furhter modified to afford carbocyclic (E)-5-(2-bromovinyl)-2'-deoxyuridine (25b) and its α-epimer (25a), respectively.
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 (E)-5-(2-bromovinyl)-2'-deoxyuridine: A potent antiherpes agent
Cookson,Dudfield,Newton,et al.
, p. 375 - 377 (2007/10/02)
The synthesis and antiherpes activity of (±)-carbocyclic (E)-5-(2 bromovinyl)-2'-deoxyuridine 1b is described. Compound 1b shows potent activity against HSV-1 in vitro, whereas its α-epimer 2 is only weakly active. The phosphorylation rates of 1b and 2 by HSV thymidine kinases are reported.
