Chemistry of Natural Compounds

, Volume 52, Issue 3, pp 555–557 | Cite as

Synthesis of Ursolic Acid Conjugates Containing a Furoxan Moiety

  • S. A. PopovEmail author
  • L. M. Kornaukhova
  • A. V. Shpatov
  • I. A. Grigor’ev

Recently, nonsteroidal anti-inflammatory drugs (NSAIDs) combined with NO donors (NO-NSAIDs) are attracting attention and are considered promising anti-cancer chemotherapy agents [1]. Compared with ordinary NSAIDs, NO-NSAIDs have low toxicity and fewer side effects, in particular, damage to the gastrointestinal tract and kidneys [2]. The use of NO donors in hybrids with NSAIDs can lead to synergism and increased anti-inflammatory activity [3]. Derivatives of 1,2,5-oxadiazole-2-oxide (furoxan) can be used as the NO donor. The synthesis of the conjugate of diclofenac and a furoxan derivative that exhibited high anti-inflammatory activity was reported [4]. Furoxan derivatives have been reported to have also antithrombotic [5], vasodilating [6], and bactericidal [7] activities.

According to the literature, slightly toxic ursolic acid (UA) and several of its derivatives also had noticeable antiinflammatory activity [8]. Ursane-type compounds are being actively studied as potential...


CDCl3 CH2Cl2 Succinic Acid Diester Ursolic Acid 
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The work was performed under the auspices of Project No. 12 of collaborative basic research between the Belarus NAS and the SB RAS.


  1. 1.
    M. Chattopadhyaya, R. Kodela, K. R. Olson, and K. Kashfi, Biochem. Biophys. Res. Commun., 419, 523 (2012).CrossRefGoogle Scholar
  2. 2.
    P. del Soldato, R. Sorrentino, and A. Pinto, Trends Pharmacol. Sci., 20, 319 (1999).CrossRefPubMedGoogle Scholar
  3. 3.
    S. Fiorucci, L. Santucci, E. Antonelli, E. Distrutti, G. Del Sero, O. Morelli, L. Romani, B. Federici, P. Del Soldato, and A. Morelli, Gasteroenterology, 118, 404 (2000); S. Fiorucci, L. Santucci, G. Cirino, A. Mencarelli, L. Familiari, P. Del Soldato, and A. Morelli, J. Immunol., 165, 5245 (2000); Y. M. Kim, R. V. Talanian, J. Li, and T. R. Billiar, J. Immunol., 161, 4122 (1998); J. J. Kerwin and M. Heller, Med. Res. Rev., 14 (1), 23 (1994).Google Scholar
  4. 4.
    J. Pedrazzoli, A. Gambero, and P. S. De Carvalho, USA Pat. Appl. 20080114038 A1, May 15, 2008.Google Scholar
  5. 5.
    C. Cena, S. Visentin, A. Gasco, P. A. Martorana, R. Fruttero, and A. Gasco, Farmaco, 57 (5), 417 (2002).CrossRefPubMedGoogle Scholar
  6. 6.
    K. Chegaev, B. Rolando, S. Guglielmo, R. Fruttero, and A. Gasco, J. Heterocycl. Chem., 46 (5), 866 (2009).CrossRefGoogle Scholar
  7. 7.
    M. B. Gravestock, D. G. Acton, M. J. Betts, M. Dennis, G. Hatter, A. S. M. L. McGregor, R. G. Wilson, L. Woods, and A. Wookey, Bioorg. Med. Chem. Lett., 13 (23), 4179 (2003).CrossRefPubMedGoogle Scholar
  8. 8.
    Y. Ikeda, A. Murakami, and H. Ohigashi, Mol. Nutr. Food Res., 52, 26 (2008); M. C. Aguirre, C. Delporte, N. Backhouse, S. Erazo, M. E. Letelier, B. K. Cassels, X. Silva, S. Alegria, and R. Negrete, Bioorg. Med. Chem., 14 (16), 5673 (2006).Google Scholar
  9. 9.
    L. Chen, W. Qui, J. Tang, Z. F. Wang, and S. Y. He, Chin. Chem. Lett., 22 (4), 413 (2011). 10. A. M. Gasco, D. Boschi, and A. Gasco, J. Heterocycl. Chem., 32, 811 (1995).Google Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • S. A. Popov
    • 1
    Email author
  • L. M. Kornaukhova
    • 1
  • A. V. Shpatov
    • 1
  • I. A. Grigor’ev
    • 1
  1. 1.Novosibirsk Institute of Organic ChemistryNovosibirskRussia

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