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Chemistry of Heterocyclic Compounds

, Volume 25, Issue 5, pp 535–540 | Cite as

Analogs of purine nucleosides. 4. 7-Alkylated 9-(2-hydeoxymethyl)guanine

  • M. A. Madre
  • R. A. Zhuk
  • M. Yu. Lidak
Article
  • 43 Downloads

Abstract

7,9-Disubstituted guaninium hydrohalides were synthesized by the reaction of 9- and 7-(2-hydroxymethyl)guanines with alkyl halides. The effect of the structure of the alkylating agent on the direction and yield of the alkylation reaction was established. The possibility of the conversion of the salts obtained to the free bases in a weakly alkaline medium was investigated. The synthesized compounds were characterized by the UV and 1H and 13C NMR spectra. The ability of the synthesized compounds to inhibit replication of the herpes virus (VPG-1) was demonstrated.

Keywords

Organic Chemistry Alkylation Purine Nucleoside Guanine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature Cited

  1. 1.
    M. A. Madre, É. É. Liepin'sh, R. A. Zhuk, O. V. Sakhartova, and M. Yu. Lidak, Khim. Geterotsikl. Soedin., No. 4, 518 (1986).Google Scholar
  2. 2.
    J. W. Jones and R. K. Robins, J. Am. Chem. Soc., 84, 1914 (1962).Google Scholar
  3. 3.
    H. Bredereck, O. Christmann, W. Koser, P. Schellenberg, and R. Nast, Chem. Ber., 95, 1812 (1962).Google Scholar
  4. 4.
    W. Pfleiderer and F. Sagi, Annalen, 673, 78 (1964).Google Scholar
  5. 5.
    J. W. Jones and R. K. Robins, J. Am. Chem. Soc., 85, 193 (1962).Google Scholar
  6. 6.
    Z. A. Shabarova and A. A. Bogdanov, The Chemistry of Nucleic Acids and Their Components [in Russian], Khimiya, Moscow (1978), p. 63.Google Scholar
  7. 7.
    H. C. Box, K. T. Lilga, J. B. French, G. Potienko, and J. L. Alderfer, J. Carbohydr. Nucleosides, Nucleotides, 8, 189 (1981).Google Scholar
  8. 8.
    R. C. Moschel, W. R. Hudgins, and A. Dipple, J. Org. Chem., 49, 363 (1984).Google Scholar
  9. 9.
    European Patent No. 161955 A, M. MacCoss, R. L. Tolman, and R. A. Strelitz, Chem. Abstr., 104, 207063 (1986).Google Scholar
  10. 10.
    M. A. Madre, R. A. Zhuk, and M. Yu. Lidak, Khim.-farm. Zh., 19, 1371 (1985).Google Scholar
  11. 11.
    J. H. Lister, Fused Pyrimidines. Part 2, Purines, edited by D. J. Brown, Interscience, New York-London (1971), p. 494.Google Scholar
  12. 12.
    P. Brookes, A. Dipple, and P. D. Lawley, J. Chem. Soc., No. 6, 2026 (1968).Google Scholar

Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • M. A. Madre
    • 1
  • R. A. Zhuk
    • 1
  • M. Yu. Lidak
    • 1
  1. 1.Institute of Organic SynthesisAcademy of Sciences of the Latvian SSRRiga

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