Skip to main content
SpringerLink
Log in

Synthesis of N-(6-benzylthio-9H-9-purinyl)acetylamino acids

  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    6-Mercaptopurine derivatives containing amino acid residues at the nitrogen of the imidazole ring (N-9) were obtained.

  2. 2.

    A single-stage method involving the action of the appropriate N-bromoacetylamino acid esters on 6-benzylmercaptopurine (in dimethyl sulfoxide and in the presence of potassium carbonate) was proposed for the preparation of N-(6-benzylthio-9H-9-purinyl)acetylamino esters. Ethyl and benzyl esters of N-(6-benzylthio-9H-9-purinyl)acetylglycine and the corresponding alanine, valine, leucine, and phenylalanine derivatives (VIII a-e and VIII a1-e1) and also the ethyl esters of N-(6-benzylthio-9H-9-purinyl)acetylsarcolysine (VIII f) and the corresponding L-valine derivatives were obtained.

  3. 3.

    The corresponding N-(6-benzylthio-9H-9-purinyl)acetylamino acids (IX a-f) were obtained from the ethyl esters.

  4. 4.

    N-(6- Benzylthio-9H-9-purinyl)acetylvaline (IX c) and N-(6-benzylthio-9H-9-purinyl)acetylglycine ethyl ester were obtained from 6-benzylmercaptopurine by the multirange method A through the ethyl ester, hydrazide, and azide of 6-benzylthio-9H-9-purinylacetic acid. A by-product of the reaction (6-benzylthio-9H-9-purinylacetic acid) was isolated.

  5. 5.

    The ethyl and benzyl esters of N-bromoacetylglycine and the corresponding alanine, valine, leucine, and phenylalanine compounds and the ethyl esters of N-bromoacetylsarcolysine and the corresponding L-valine compounds were obtained as initial products.

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. J. F. Gerster and R. K. Robins, J. Am. Chem. Soc.,87, 3752 (1965).

    Google Scholar 

  2. E. D. Kaverzneva, V. K. Zvorykina, and V. V. Kiseleva, Izv. Akad. Nauk SSSR, Ser. Khim., 1199 (1966).

  3. E. D. Kaverzneva, V. K. Zvorykina, V. V. Kiseleva and T. A. Gorokhova, Izv. Akad. Nauk SSSR, Ser. Khim., 2148 (1966).

  4. B. R. Baker and P. M. Tanna, J. Pharm. Sci.,54, 1609 (1965); Chem. Abs.,63, 18872g (1965).

    Google Scholar 

  5. M. Yu. Lidak, Ya. Ya. Shluke, and Yu. P. Shvachkin, Khim. Geterotsikl. Soed., 955 (1968).

  6. R. K. Robins, J. Med. Chem.,7, 186 (1964); D. E. O'Brien, J. D. Westover, R. K. Robins, and C. C. Cheng, J. Med. Chem.,8, 182 (1965); J. A. Johnson, H. J. Thomas, and H. J. Schaeffer, J. Am. Chem. Soc.,80, 699 (1958).

    Google Scholar 

  7. J. A. Montgomery and C. Temple, J. Am. Chem. Soc.,83, 630 (1961).

    Google Scholar 

  8. G. B. Elion, W. H. Lange and G. H. Hitchings, J. Am. Chem. Soc.,78, 2858 (1956).

    Google Scholar 

  9. M. Brenner and W. Huber, Helv. Chim. Acta,36, 1109 (1953); R.p. Patel and S. Price, J. Organ. Chem.,30, 3575 (1965).

    Google Scholar 

  10. J. Grinshtein and M. Vinits, Chemistry of Amino Acids and Peptides [Russian translation], Mir (1965), p.436.

  11. H. Roehnert, E. Carstens, and H. Barth, Ger (East), 22532 (C1. 2a) Jan.15 (1962); Chem. Abs.,58, 5520f (1963).

  12. H. Zahn and K. Mella, Hoppe Seyler's Z. Phys. Chem.,334, 75 (1966).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    E. D. Kaverzneva, V. K. Zvorykina & V. V. Kiseleva

Authors
  1. E. D. Kaverzneva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. K. Zvorykina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. V. Kiseleva
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Deceased

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2295–2304, October, 1970.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kaverzneva, E.D., Zvorykina, V.K. & Kiseleva, V.V. Synthesis of N-(6-benzylthio-9H-9-purinyl)acetylamino acids. Russ Chem Bull 19, 2157–2166 (1970). https://doi.org/10.1007/BF00861489

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00861489

Keywords

Search

Navigation