Synthesis 2012; 44(15): 2359-2364
DOI: 10.1055/s-0031-1289812
paper
© Georg Thieme Verlag Stuttgart · New York

A New Approach to the Synthesis of Acyclic Nucleotide Phosphonate Analogues with Triple or Double Bonds

Valery K. Brel*
Institute of Physiologically Active Compounds of Russian Academy of Sciences, Chernogolovka, Moscow Region 142432, Russian Federation, Fax: +7(495)7857024   Email: brel@ipac.ac.ru
› Author Affiliations
Further Information

Publication History

Received: 26 March 2012

Accepted after revision: 14 May 2012

Publication Date:
26 June 2012 (online)


Abstract

On the basis of new methodology to design the phosphonate analogues of nucleotides, the first series of acyclic nucleotides possessing a triple bond in the carbon skeleton were prepared by coupling diethyl 4-chlorobuta-1,2-dienylphosphonate with the corresponding purine or pyrimidine nucleic bases under base-catalyzed alkylation conditions.

 
  • References

    • 1a De Clercq E. J. Clin. Virol.. 2004; 30: 115
    • 1b Chu CK, Baker DC. Nucleosides and Nucleotides as Antitumour and Antiviral Agents. New York: Plenum Press; 1993
    • 1c Naesens L, Balzarini J, De Clercq E. Rev. Med. Virol. 1994; 4: 147
    • 1d Chu CK, Cutler SJ. J. Heterocycl. Chem. 1986; 23: 289
    • 1e Naesens L, De Clercq E. Nucleosides Nucleotides 1997; 16: 983
    • 2a Blick G, Garton T, Hopkins U, Lagravinese L. J. Acquired Immune Defic. Syndr. Hum. Retrovirol. 1997; 15: 84
    • 2b Cundy KC, Barditch-Crovo PA, Walker RE, Collier AC, Ebeling D, Toole J, Jaffe HS. Antimicrob. Agents Chemother. 1995; 39: 2401
  • 3 Kirsch LS, Arevalo JF, Delapaz EC, Munguia D, De Clercq E, Freeman WR. Ophthalmology 1995; 102: 533
    • 4a De Clercq E, Holý A, Rosenberg I, Sakuma T, Balzarini J, Maudgal PC. Nature (London) 1986; 323: 464
    • 4b De Clercq E, Sakuma T, Baba M, Pauwels R, Balzarini J, Rosenberg I, Holý A. Antiviral Res. 1987; 8: 261
    • 4c Naesens L, De Clercq E. Herpes 2001; 8: 12
    • 5a Heijtink RA, Dewilde GA, Kruining J, Berk L, Balzarini J, De Clercq E, Holý A, Schalm SW. Antiviral Res. 1993; 21: 141
    • 5b Yokota T, Konno K, Shigeta S, Holý A, Balzarini J, De Clercq E. Antiviral Chem. Chemother. 1994; 5: 57
    • 5c Luscombe C, Pedersen J, Uren E, Locarnini S. Hepatology 1996; 24: 766
    • 6a Mitauya H, Yarchoan R, Broder S. Science (Washington, D. C.) 1990; 249: 1533
    • 6b Megati S, Phadtare S, Zemlicka J. J. Org. Chem. 1992; 57: 2320
    • 6c Phadtare S, Zemlicka J. J. Am. Chem. Soc. 1989; 111: 5925
    • 6d Harnden MR, Parkin A, Parratt MJ, Perkins RM. J. Med. Chem. 1993; 36: 1343
    • 6e Casara PJ, Alenburger J.-M, Taylor DL, Tyms AS, Kenny M, Nave J.-F. Bioorg. Med. Chem. Lett. 1995; 5: 1275
    • 6f Jeon GS, Bentrude WG. Tetrahedron Lett. 1998; 39: 927
    • 6g Lazrek HB, Rochdi A, Khaider H, Barascut J.-L, Imbach J.-L, Balzarini J, Witvrouw M, Pannecouque C, De Clercq E. Tetrahedron 1998; 54: 3807
    • 7a Engel R. Synthesis of Carbon-Phosphorus Bonds . CRS Press; Boca Raton: 1988
    • 7b Krayevsky AA, Watanabe KA. Modified Nucleosides as Anti-Aids Drugs: Current Status and Perspectives. Bioinform; Moscow: 1993. 98
  • 8 Almer H, Classon B, Samuelsson B, Kvarnström I. Acta Chem. Scand. 1991; 45: 766
  • 9 Brel VK. Heteroat. Chem. 2006; 17: 547
  • 10 Brel VK, Belsky VK, Stash AI, Zavodnik VE, Stang PJ. Eur. J. Org. Chem. 2005; 512
  • 11 Brel VK, Belsky VK, Stash AI, Zavodnik VE, Stang PJ. Org. Biomol. Chem. 2003; 1: 4220
  • 12 Brel VK. Phosphorus, Sulfur Silicon Relat. Elem. 2002; 177: 1933
  • 13 Mark V. Tetrahedron Lett. 1962; 3: 281
  • 14 Lim MI, Marquez VE. Tetrahedron Lett. 1985; 26: 3669
  • 15 Medich JR, Kunnen KB, Johnson CR. Tetrahedron Lett. 1985; 26: 3669
    • 16a Holý A, Rosenberg I, Dvořáková H. Collect. Czech. Chem. Commun. 1989; 54: 2190
    • 16b Holý A, Zidek Z, Votruba I. Collect. Czech. Chem. Commun. 1996; 61: S182
    • 16c Holý A, Günter J, Dvořáková H, Vasojídková M, Andrei G, Snoeck R, Balzarini J, De Clercq E. J. Med. Chem. 1999; 42: 2064
    • 16d Hakimelahi GH, Ly TW, Moosavi-Movahedi AA, Jain ML, Zakerinia M, Davari H, Mei H.-C, Sambaiah T, Moshfegh AA. J. Med. Chem. 2001; 44: 3710
  • 17 Brel VK, Stang PJ. Eur. J. Org. Chem. 2003; 224