Synthesis of Ursolic Acid Conjugates Containing a Furoxan Moiety
- 91 Downloads
Recently, nonsteroidal anti-inflammatory drugs (NSAIDs) combined with NO donors (NO-NSAIDs) are attracting attention and are considered promising anti-cancer chemotherapy agents . Compared with ordinary NSAIDs, NO-NSAIDs have low toxicity and fewer side effects, in particular, damage to the gastrointestinal tract and kidneys . The use of NO donors in hybrids with NSAIDs can lead to synergism and increased anti-inflammatory activity . 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 . Furoxan derivatives have been reported to have also antithrombotic , vasodilating , and bactericidal  activities.
According to the literature, slightly toxic ursolic acid (UA) and several of its derivatives also had noticeable antiinflammatory activity . Ursane-type compounds are being actively studied as potential...
KeywordsCDCl3 CH2Cl2 Succinic Acid Diester Ursolic Acid
The work was performed under the auspices of Project No. 12 of collaborative basic research between the Belarus NAS and the SB RAS.
- 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.J. Pedrazzoli, A. Gambero, and P. S. De Carvalho, USA Pat. Appl. 20080114038 A1, May 15, 2008.Google Scholar
- 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.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