Chemistry of Natural Compounds

, Volume 45, Issue 3, pp 338–345 | Cite as

Plant coumarins. 4.* Synthesis of N-containing derivatives of oreoselone

  • A. V. Lipeeva
  • E. E. Shul’ts
  • M. M. Shakirov
  • G. A. Tolstikov

Bromination of peucedanin by various reagents was studied. Conditions for forming 2-(1,3-dibromopropan-2-ylidene)-2H-furo[3,2-g][1]benzopyran-3,7-dione were found. Several 2-aminofuranocoumarins were synthesized by reaction of 2-bromoreoselone with derivatives of pyrrolidine, piperidine, and piperazine. The new compounds were interesting as potential biologically active compounds.

Key words

furanocoumarins bromoreoselone 2-(1-methylethylidene)-7H-furo[3,2-g][1]benzopyran-3,7-dione 



The work was supported financially by the Russian Foundation for Basic Research (Project No. 08-03-90200-Mong_a).


  1. 1.
    Zh. Ganbaatar, B. Gantumur, S. A. Osadchii, E. E. Shul'ts, M. M. Shakirov, and G. A. Tolstikov, Khim. Prir. Soedin., 468 (2008).Google Scholar
  2. 2.
    R. D. H. Murray, Nat. Prod. Rep., 12, 477 (1995).CrossRefGoogle Scholar
  3. 3.
    B. M. Malikov and A. I. Saidkhodzhaev, Khim. Prir. Soedin., 250 (1998); 384 (1998); 560 (1998).Google Scholar
  4. 4.
    F. Borges, F. Roleira, N. Mihazes, L. Santana, and E. Uriarte, Curr. Med. Chem., 12, 887 (2005).PubMedCrossRefGoogle Scholar
  5. 5.
    O. Thastrup, B. Fjalland, and J. Lemmich, Acta Pharmacol. Toxicol., 52, 246 (1983).Google Scholar
  6. 6.
    S. Y. Kang, K. J. Lee, S. H. Sung, M. J. Park, and J. C. Kim, J. Nat. Prod., 64, 683 (2001).PubMedCrossRefGoogle Scholar
  7. 7.
    R. Tovar-Miranda, R. Cortes-Garcia, N. F. Santos-Sanchez, and P. Joseph-Nathan, J. Nat. Prod., 61, 1216 (1998).PubMedCrossRefGoogle Scholar
  8. 8.
    L. Santana, H. Gonzalez-Diaz, E. Quezada, E. Uriarte, M. Yanez, D. Vina, and F. Orallo, J. Med. Chem., 51, 6740 (2008).PubMedCrossRefGoogle Scholar
  9. 9.
    E. E. Shul'ts, T. N. Petrova, M. M. Shakirov, E. I. Chernyak, L. M. Pokrovskii, S. A. Nekhoroshev, and G. A. Tolstikov, Khim. Interesakh Ustoich. Razvit., 11, 683 (2003).Google Scholar
  10. 10.
    S. A. Osadchii, E. E. Shul'ts, M. M. Shakirov, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., No. 2, 362 (2006).Google Scholar
  11. 11.
    I. A. Bagryanskaya, Yu. V. Gatilov, S. A. Osadchii, A. A. Martynov, M. M. Shakirov, E. E. Shul'ts, and G. A. Tolstikov, Khim. Prir. Soedin., 541 (2005).Google Scholar
  12. 12.
    F. Bruchhausen and H. Hoffman, Ber. Dtsch. Chem. Ges. B, 74, 1584 (1941).CrossRefGoogle Scholar
  13. 13.
    C. A. Contogiorgis and D. J. Hadjipavlou-Latina, J. Med. Chem., 48, 6400 (2005).CrossRefGoogle Scholar
  14. 14.
    W. P. Weber and G. W. Goekel, Phase Transfer Catalysis in Organic Synthesis, Springer-Verlag, Berlin and New York, 1977.Google Scholar
  15. 15.
    H. A. Muathen, Synthesis, 169 (2002).Google Scholar
  16. 16.
    A. Orechov and G. Menschikoff, Ber. Dtsch. Chem. Ges., 64, 266 (1931).CrossRefGoogle Scholar
  17. 17.
    A. S. Sadykov, Chemistry of Alkaloids from Anabasis aphylla [in Russian], Izd. Akad. Nauk Uzb. SSR, Tashkent, 1956.Google Scholar
  18. 18.
    R. A. Konovalova, S. Yunusov, and A. P. Orekhov, Zh. Obshch. Khim., 9, No. 15, 1356 (1939).Google Scholar
  19. 19.
    V. G. Zakharov, N. I. Libizov, and Kh. A. Aslanov, Drugs from Plants and Their Production Methods [in Russian], Izd. Fan, Uzb. SSR, Tashkent, 1980.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • A. V. Lipeeva
    • 1
  • E. E. Shul’ts
    • 1
  • M. M. Shakirov
    • 1
  • G. A. Tolstikov
    • 1
  1. 1.N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian BranchRussian Academy of SciencesNovosibirskRussia

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