Synthesis, Protonation Behavior, Conformational Analysis, and Regioselective Enzymatic Acylation of the Novel Diamino Analogue of (E)-5-(2-Bromovinyl)-2′-deoxyuridine (BVDU)

Author:

Lavandera Iván1,Fernández Susana1,Ferrero Miguel1,De Clercq Erik2,Gotor Vicente13

Affiliation:

1. a Departamento de Química Orgánica e Inorgánica , Facultad de Química , Universidad de Oviedo , Oviedo, Spain

2. b Rega Institute for Medical Research , Katholieke Universiteit Leuven , Leuven, Belgium

3. c Departamento de Química Orgánica e Inorgánica , Facultad de Química , Universidad de Oviedo , 33071, Oviedo, Spain

Publisher

Informa UK Limited

Subject

Genetics,Molecular Medicine,Biochemistry,General Medicine

Reference15 articles.

1. (a) Robins, R.K.; Revankar, G.R.Antiviral Drug Development; De Clercq, E., Walker, R.T., Eds.; Plenum Press: New York, 1998; 11 pp; (b)Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C.K., Baker, D.C., Eds.; Plenum Press: New York, 1993; (c) MacCoss, M.; Robins, M.J.Chemistry of Antitumor Agents; Wilman, D.E.V., Ed.; Blackie and Son: U.K., 1990; 261 pp; (d) Robins, R.K.; Kini, G.D.Chemistry of Antitumor Agents; William, D.E.V., Ed.; Blackie and Sons: U.K., 1990; 299 pp; (e)Chemistry of Nucleosides and Nucleotides; Townsend, L.B., Ed.; Plenum Press: New York, 1988

2. 3'-Azido-3'-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro.

3. (a) De Clercq, E. Targets for the antiviral activity of pyrimidine and purine nucleoside analogs. Nucleosides Nucleotides1987,6, 197–207; (b) De Clercq, E. Antiviral and antitumor activities of 5-substituted 2′-deoxyuridines.Meth. Find Exptl. Clin. Pharmacol.1980,2, 253–267

4. (a) De Clercq, E. Biochemical aspects of the selective antiherpes activity of nucleoside analogs.Biochem. Pharmacol.1984,33, 2159–2169; (b) De Clercq, E.; Descamps, J.; Ogata, M.; Shigeta, S. In vitro susceptibility of varicella-zoster virus to E-5-(2-bromovinyl)-2′-deoxyuridine and related compounds.Antimicrob. Agents Chemother.1982,21, 33–38; (c) De Clercq, E.; Descamps, J.; Verhelst, G.; Walker, R.T.; Jones, A.S.; Torrence, P.F.; Shugar, D. Comparative efficacy of antiherpes drugs against different strains of herpes simplex virus.J. Infect. Dis.1980,141, 563–574; (d) De Clercq, E.; Descamps, J.; De Somer, P.; Barr, P.J.; Jones, A.S.; Walker, R.T. (E)-5-(2-bromovinyl)-2′-deoxyuridine: A potent and selective anti-herpes agent.Proc. Natl. Acad. Sci. USA1979,76, 2947–2951

5. Mechanism of Antiviral Action of (E)-5-(2-Bromovinyl)-2′-Deoxyuridine (BVDU): Direct Evidence with [14C]BVDU in Herpes Simplex Virus-Infected Cells

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