Skip to main content
SpringerLink
Log in

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

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature Cited

  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. J. W. Jones and R. K. Robins, J. Am. Chem. Soc., 84, 1914 (1962).

    Google Scholar 

  3. H. Bredereck, O. Christmann, W. Koser, P. Schellenberg, and R. Nast, Chem. Ber., 95, 1812 (1962).

    Google Scholar 

  4. W. Pfleiderer and F. Sagi, Annalen, 673, 78 (1964).

    Google Scholar 

  5. J. W. Jones and R. K. Robins, J. Am. Chem. Soc., 85, 193 (1962).

    Google Scholar 

  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. 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. R. C. Moschel, W. R. Hudgins, and A. Dipple, J. Org. Chem., 49, 363 (1984).

    Google Scholar 

  9. European Patent No. 161955 A, M. MacCoss, R. L. Tolman, and R. A. Strelitz, Chem. Abstr., 104, 207063 (1986).

    Google Scholar 

  10. M. A. Madre, R. A. Zhuk, and M. Yu. Lidak, Khim.-farm. Zh., 19, 1371 (1985).

    Google Scholar 

  11. J. H. Lister, Fused Pyrimidines. Part 2, Purines, edited by D. J. Brown, Interscience, New York-London (1971), p. 494.

    Google Scholar 

  12. P. Brookes, A. Dipple, and P. D. Lawley, J. Chem. Soc., No. 6, 2026 (1968).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, 226006, Riga

    M. A. Madre, R. A. Zhuk & M. Yu. Lidak

Authors
  1. M. A. Madre
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. A. Zhuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Yu. Lidak
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See [1] for Communication 3.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 641–646, May, 1989.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Madre, M.A., Zhuk, R.A. & Lidak, M.Y. Analogs of purine nucleosides. 4. 7-Alkylated 9-(2-hydeoxymethyl)guanine. Chem Heterocycl Compd 25, 535–540 (1989). https://doi.org/10.1007/BF00482501

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00482501

Keywords

Search

Navigation