Skip to main content
SpringerLink
Log in

Synthesis of 3-O-aryl esters of (R,S)-9-(2,3-dihydoxypropyl)adenine and its pyrimidine analogs as new potential inhibitors ofS-adenosyl-L-homocysteine hydrolase

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

With the aim of searching for new antiviral agents of the acyclonucleoside type, 3-O-arly esters of (R,S)-9-(2,3-dihydroxypropyl)adenine adenine and its pyrimidine analogs have been synthesized. Alkylation of adenine and cytosine by aryl glycidyl ethers in the presence of potassium carbonate affords 46–76% yields of the corresponding N9- and N1-substituted derivatives. The interaction of aryl glycidyl ethers with trimethylsilyl derivatives of uracil and thymine also results in 41–57% yields of N1-monosubstituted products with identical acyclic chain structure.

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

References

  1. E. De Clercq, Biochem. Pharmacol.,36, 2567 (1987).

    Google Scholar 

  2. M. S. Wolfe and R. T. Borchardt, J. Med. Chem.,34, 1521 (1991).

    Google Scholar 

  3. E. De Clercq, J. Descamps, P. De Somer, and A. Holy, Science,200, 563 (1978).

    Google Scholar 

  4. E. De Clercq and A. Holy, J. Med. Chem.,22, 510 (1979).

    Google Scholar 

  5. Y. Votruba and A. Holy, Collect. Czech. Chem. Commun.,47, 167 (1982).

    Google Scholar 

  6. E. De Clercq and A. Holy, J. Med. Chem.,28, 282 (1985).

    Google Scholar 

  7. M. Cools and E. De Clercq, Biochem. Pharmacol.,38, 1061 (1989).

    Google Scholar 

  8. E. De Clercq, Antimicrob. Agents Chemother.,28, 84 (1985).

    Google Scholar 

  9. R. T. Borchardt, B. T. Keller, and U. Patel-Trombre, J. Biol. Chem.,259, 4353 (1984).

    Google Scholar 

  10. J. C. Martin, D. F. Smee, and J. P. H. Verheyden, J. Org. Chem.,50, 755 (1985).

    Google Scholar 

  11. M. S. Novikov, A. K. Brel', A. A. Ozerov, and G. I. Parsheva, Zh. Org. Khim.,27, 1919 (1991).

    Google Scholar 

Download references

Authors
  1. A. A. Ozerov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. S. Novikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. K. Brel'
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Scientific-Research Institute of Pharmacology at the Volgograd Medical Academy, Volgograd 400066, Russia.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 82–86, January, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ozerov, A.A., Novikov, M.S. & Brel', A.K. Synthesis of 3-O-aryl esters of (R,S)-9-(2,3-dihydoxypropyl)adenine and its pyrimidine analogs as new potential inhibitors ofS-adenosyl-L-homocysteine hydrolase. Chem Heterocycl Compd 35, 78–83 (1999). https://doi.org/10.1007/BF02251667

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02251667

Keywords

Search

Navigation