Russian Journal of Organic Chemistry

, Volume 41, Issue 3, pp 396–401 | Cite as

Selenium-Containing Heterocycles. Synthesis and Reactions of 2-Amino-4,5,6,7-tetrahydro-1-benzoselenophene-3-carbonitrile with Anticipated Biological Activity

  • Sh. H. Abdel-Hafez


Reaction of 2-amino-4,5,6,7-tetrahydro-1-benzoselenophene-3-carbonitrile with ethylenediamine in the presence of a catalytic amount of carbon disulfide afforded 2-amino-3-(4,5-dihydro-1H-imidazol-2-yl)-4,5,6,7-tetrahydro-1-benzoselenophene. Cyclocondensation of the latter with triethyl orthoformate, benzaldehyde, and carbon disulfide gave tetracyclic imidazobenzoselenophenopyrimidine derivatives. Treatment of 2,3,5,6,8,9,10,11-octahydroimidazo[2,1-c][1]benzoselenopheno[3,2-e]pyrimidine-5-thione with hydrazine hydrate led to the corresponding 5-hydrazino derivative whose reactions with triethyl orthoformate and sodium nitrite were accompanied by closure of 1,2,4-triazole and tetrazole rings, respectively. Fused benzoseleno-phenopyrimidine systems were also obtained by reaction of 2-amino-4,5,6,7-tetrahydrobenzo-1-selenophene-3-carbonitrile with formamide, carbon disulfide, and phenyl isothiocyanate. Some newly synthesized compounds were tested for antimicrobial and antifungal activity.


Nitrite Hydrazine Antifungal Activity Benzaldehyde Isothiocyanate 


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  1. 1.
    Litvinov, V.P. and Dyachenko, V.D., Russ. Chem. Rev., 1997, vol. 66, p. 923.Google Scholar
  2. 2.
    Paulmier, C., Selenium Reagents and Intermediates in Organic Synthesis, Oxford: Pergamon, 1986.Google Scholar
  3. 3.
    Wirth, T., Tetrahedron, 1999, vol. 55, p. 1; Organoselenium Chemistry. Topics in Current Chemistry, Wirth, T., Ed., Berlin: Springer, 2000, p. 208.Google Scholar
  4. 4.
    Organoselenium Chemistry, A Practical Approach, Black, T.G., Ed., Oxford: Oxford Univ., 1999.Google Scholar
  5. 5.
    Atanassov, P.K., Zhou, Y., Linden, A., and Heimgartner, H., Helv. Chim. Acta, 2002, vol. 85, p. 1102.Google Scholar
  6. 6.
    Gasparian, A.V., Yao, Y.J., Lu, J., Yemelyanov, A.Y., Lyakh, L.A., Slaga, J.T., and Budunova, I.V., Mol. Cancer Ther., 2002, vol. 1, p. 1079.PubMedGoogle Scholar
  7. 7.
    Fleming, J., Ghose, A., and Harrison, P.R., Nutr. Cancer, 2001, vol. 40, p. 42.PubMedGoogle Scholar
  8. 8.
    Ghose, A., Fleming, J., El-Bayoumy, K., and Harrison, P.R., Cancer Res., 2001, vol. 61, p. 7479.PubMedGoogle Scholar
  9. 9.
    Wu, W., Murakami, K., Koketsu, M., and Saiki, I., Anticancer Res., 1999, vol. 19, p. 5375.PubMedGoogle Scholar
  10. 10.
    Hu, C., Zhang, P., Li, H., Ji, Z., and Liu, B., Huaxue Tongbao, 2002, vol. 65, p. 162; Chem. Abstr., 2002, vol. 137, no. 169 434.Google Scholar
  11. 11.
    Koketsu, M., Senda, T., and Ishihara, H., JPN Patent no. 2000-119 263, 2000; Chem. Abstr., 2000, vol. 132, no. 293 768.Google Scholar
  12. 12.
    Janzuu, S., Appell, G., Chaudiere, J., and Yadan, J.-C., JPN Patent no. 11-140 067, 1999; Chem. Abstr., 1999, vol. 131, no. 32 054.Google Scholar
  13. 13.
    Koketsu, M., Tanaka, K., Takenaka, Y., Kwong, C.D., and Ishihara, H., Eur. J. Pharm. Sci., 2002, vol. 15, p. 307.PubMedGoogle Scholar
  14. 14.
    Sibor, J. and Pazdera, P., Molecules, 1996, vol. 1, p. 157.Google Scholar
  15. 15.
    Abdel-Hafez, Sh.H., Phosphorus, Sulfur, Silicon, 2003, vol. 178, p. 2563.Google Scholar
  16. 16.
    Abbady, M.A. and Abdel-Hafez, Sh.H., Phosphorus, Sulfur, Silicon, 2000, vol. 160, p. 121.Google Scholar
  17. 17.
    Abbady, M.A., Abdel-Hafez, Sh.H., Kandeel, M.M., and Abdel-Monem, M.I., Molecules, 2003, vol. 8, p. 622.Google Scholar
  18. 18.
    Radwan, Sh.M. and El-Kashef, H.S., Farmaco, 1998, vol. 53, p. 113.PubMedGoogle Scholar
  19. 19.
    Youssefyeh, R.D., Brown, R.E., Wilson, J., Shahm, U., et al., J. Med. Chem., 1984, vol. 27, p. 1639.PubMedGoogle Scholar
  20. 20.
    Carrod, L.P. and Grady, F.D., Antibiotics and Chemotherapy, Edinburgh: Churchill Livingston, 1972, 3rd ed., p. 477.Google Scholar
  21. 21.
    Cremer, A., Antibiotic Sensitivity and Assay Tests, London: Butterworth, 1980, 4th ed., p. 521.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • Sh. H. Abdel-Hafez
    • 1
  1. 1.Chemistry Department, Faculty of ScienceAssiut UniversityAssiutEgypt

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