Archives of Pharmacal Research

, Volume 17, Issue 2, pp 60–65 | Cite as

Synthesis and quartermization of 6-(substitutedamino)-purines with antitumor activity screening

  • Khairy A. M. El-Bayouki
  • Wahid M. Basyouni
  • S. M. El-Din
  • A. G. Habeeb
Research Articles


Reaction of 6-chloro-9-benzyl-8-(methylthio)purine3 with primary amines afforded, the corresponding 6-(substitutedamino)purines4a-g. The latter products when methylated with methyl iodide yielded smoothly N3-methyl purinium iodide salts5a-f rather than the probable N1-and N7-derivatives. 9-Benzyl-3-methyl-6-(methylimino)-8-(methylthio)purine8 was obtained upon treating the purinium iodide5a with alkali. Most of the synthesized compounds were screened for their antitumor activity.

Key words

Substifutedamino-purines Quartemization Antitumor activity 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References Cited

  1. Bharat, T. and Brumo, R., N6-Disubstituted adenosines: Synthesis and structure-activity relationships.J. Med. Chem., 32(8), 1667–1673 (1989).CrossRefGoogle Scholar
  2. Dutta, S. P., Tritsch, G. L., Cox, C. and Chheda, G. B., Synthesis and biological activities of some N6-(nitro-and amino-benzyl)adenosines.J. Med. Chem., 18 (8), 780–783 (1975).PubMedCrossRefGoogle Scholar
  3. El-Bayouki, Kh. A. M., Hammad, M., Osman, S. and Basyouni, W. M., Synthesis and quaternization of 5-amino-1-arylimidazole-4-carboxamides and their related imidazo-pyrazines.Oriental J. Chem., 2 45–50 (1986).Google Scholar
  4. El-Bayouki, Kh. A. M., El-Sayed, A. S. and Basyouni, W. M., Ethyl chloroformate/DMF in organic synthesis (I): A novel reagent for ring closure of 5-amino-1-aryl-4-imidazole carboxamides to their hypoxanthine derivatives.Gazzetta Chimica Italiana, 119, 163–165 (1989).Google Scholar
  5. El-Bayouki, Kh. A. M., Basyouni, W. M. and El-Sayed, M. M., Molluscicidal activity of newly synthesised triazolo- and tetrazolothiazolopyrimidines and related derivatives.Egypt. J. Bilharziasis, 12, 45–58 (1990).Google Scholar
  6. El-Merzabani, M. M., El-Aaser, A. A., Attia, M. A., El-Duweini, A. K. and Ghazal, A. M., Screening system for Egyptien plants with potential antitumor activity.J. Med. Plant. Res. (Planta Medica), 36, 150–155 (1979).Google Scholar
  7. Fleysher, M. M., Bloch, A., Hakala, M. T. and Nicol, C. A., Synthesis and biological activity of some new N6-substituted purine nucleosides.J. Med. Chem., 12, 1056–1061 (1969).PubMedCrossRefGoogle Scholar
  8. Johannsen, F., Jargensen, A., El-Bayouki, Kh. A. M. and Pedersen, E., Phosphorus pentaoxide in organic organic synthesis XXVI: Preparation and alkylation of furo(2,3-d) pyrimidin-4-amines.Chemica Scripta, 26, 337–342 (1986).Google Scholar
  9. Kelly, J. L. and Soroka, F. E., 9-(2-Fluorobenzyl)-6-(methylamino)-9H-purine hydrochloride: Synthesis and anticonvulsant activity.J. Med. Chem., 29, 1133–1134 (1986).CrossRefGoogle Scholar
  10. Kiyoto, I., Hajime, K. and Kiyoshi, I., 7-Hydroxyguanine compounds and their use as antitumor agents.European Patent Applied EP, 204,251 (1985);C.A. 106. 156161 (1987).Google Scholar
  11. Kozalka, G., Krentsky, T., Rideout, J. and Burns, C., Preparation of 9-β-2′-3′-dideoxyribofuranosylpurines for treatment and prophylaxix of human immunodeficiency virus infection.European Patent, EP 286,425 (1987);C.A., 111, 23910 (1989).Google Scholar
  12. Marsico, J. and Goldman, L., Site of alkylation of N6,N6-di-alkyl-9-substituted adenosines: Synthesis and alkaline degradation of 6-diethylamino-3,9-dimethylpurinium iodide.J. Org. Chem., 30, 3597–3600 (1965).CrossRefGoogle Scholar
  13. McGee, D. P. C., Martin, J. C., Smee, D. F., Matthews, T. R. and Verheyden, J. P. H., Synthesis and antiherbes simplex virus activity of 9-[(1,3-dihydroxy-2-propylthio)methyl]guanine.J. Med. Chem., 28(9), 1242–1245 (1985).PubMedCrossRefGoogle Scholar
  14. McLimans, W. F., Davis, E. V., Golve, F. I. and Rake, G. W., The submerged culture of mammalien cells: The spinner culture.J. Immunol., 79, 428–433 (1957).PubMedGoogle Scholar
  15. Moharram, H. and Osman, A., Reactions of purine derivatives with phosphorus pentaoxide and triethylamine and their antitumor effects.Arch. Pharm. Res., 12(1), 1–4 (1989).CrossRefGoogle Scholar
  16. Neiman, Z. and Bergman, F., Benzylation of 6-alkylthiopurines in aprotic solvents.Isracel J. Chem., 5, 243–245 (1967).Google Scholar
  17. Saito, T., Inous, I. and Fuji, T., Purines XLI: An alemative synthesis and the chemical behaviour of 7,9-dialkyladeninium salts.Chem. Pharm. Bull., 38(6), 1536–1547 (1990).Google Scholar
  18. Sen, A. and Sibbos, R., Synthesis of compounds related to 4(5)-aminoimidazole-5(4)-carboxamides: Part II.Ind. J. Chem., 14B, 222–225 (1976).Google Scholar
  19. Shaw, E., A new synthesis of the purines adenine, hypoxanthine, xanthine and isoguanine.J. Biol. Chem.,185, 439–447 (1950).PubMedGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea 1994

Authors and Affiliations

  • Khairy A. M. El-Bayouki
    • 1
  • Wahid M. Basyouni
    • 1
  • S. M. El-Din
    • 1
  • A. G. Habeeb
    • 1
  1. 1.National Research CenterCairoEgypt

Personalised recommendations