Russian Journal of General Chemistry

, Volume 77, Issue 10, pp 1749–1760 | Cite as

Guanidines based on tryptamine and histamine in reactions with electrophiles

  • A. S. Shestakov
  • O. E. Sidorenko
  • Kh. S. Shikhaliev
  • A. A. Pavlenko
Article
  • 35 Downloads

Abstract

Reactions of 4,6-dimethylpyrimidin-2-ylcyanamide with tryptamines and histamine gave the corresponding disubstituted guanidines. The molecular parameters of the products were calculated using GAUSSIAN 03 software package. The direction of electrophilic attack on these compounds was predicted on the basis of the geometric shape of their highest occupied molecular orbital (HOMO) and molecular electrostatic potential (MEP) maps. Acyl, carbamoyl, and cyclic derivatives were obtained, whose structure was consistent with the results of quantum-chemical calculations.

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References

  1. 1.
    Granik, V.G., Osnovy meditsinskoi khimii (Principles of Medicinal Chemistry), Moscow: Vuzovskaya Kniga, 2001, p. 84.Google Scholar
  2. 2.
    Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Khar’kov: Torsing, 1998, parts 1, 2.Google Scholar
  3. 3.
    Novak, L., Hanania, M., Kovacs, P., Kolonits, P., and Szantay, C., Synthesis, 2001, no. 1, p. 108.Google Scholar
  4. 4.
    Nekrasov, D.D., Russ. J. Org. Chem., 2004, vol. 40, no. 10, p. 1387.CrossRefGoogle Scholar
  5. 5.
    Shestakov, A.S., Gusakova, N.V., Shikhaliev, Kh.S., and Zagoruiko, A.V., Russ. J. Gen. Chem., 2006, vol. 76, no. 10, p. 1647.CrossRefGoogle Scholar
  6. 6.
    Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Vreven, T., Jr., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cros, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Paghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komafomi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Faanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Rev. C.02, Wallingford CT: Gaussian, 2004.Google Scholar
  7. 7.
    Klopman, G., J. Am. Chem. Soc., 1968, vol. 90, no. 1, p. 223.CrossRefGoogle Scholar
  8. 8.
    Clark, T., A Handbook of Computational Chemistry, New York: Wiley, 1985. Translated under the title Komp’yuternaya khimiya, Moscow: Mir, 1990, p. 171.Google Scholar
  9. 9.
    Hehre, W.J., Shusterman, A.J., and Nelson, J.E., The Molecular Modeling Workbook for Organic Chemistry, Irvine (USA): Wavefunction, 1998, p. 19.Google Scholar
  10. 10.
    Gribov, L.A. and Mushtakova, S.P., Kvantovaya khimiya (Quantum Chemistry), Moscow: Gardariki, 1999.Google Scholar
  11. 11.
    Kryl’skii, D.V., Shikhaliev, Kh.S., Shestakov, A.S., and Liberman, M.M., Russ. J. Gen. Chem., 2005, vol. 75, no. 2, p. 303.CrossRefGoogle Scholar
  12. 12.
    Filimonov, D.A. and Poroikov, V.V., Ross. Khim. Zh., 2006, vol. 50, no. 2, p. 66.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2007

Authors and Affiliations

  • A. S. Shestakov
    • 1
  • O. E. Sidorenko
    • 1
  • Kh. S. Shikhaliev
    • 1
  • A. A. Pavlenko
    • 1
  1. 1.Voronezh State UniversityVoronezhRussia

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