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The synthesis and anti-inflammatory activity of quinopimaric acid derivatives


Under the action of PCl5, the Beckman rearrangement of a 3: 1 mixture of Z- and E-isomeres of 18β-hydro-xydihydroquinopimaric acid resulted in 5′-caprolactam and isomeric caprolactams containing fragments of cyclic ether. Z- and E-ketoximes were separated as acetates. Using a carrageenan inflammation model, we demonstrated that the anti-inflammatory activity of quinopimaric acid derivatives was comparable with that of diclofenac.

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Correspondence to O. B. Kazakova.

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Original Russian Text © O.B. Kazakova, E.V. Tret’yakova, I.E. Smirnova, L.V. Spirikhin, G.A. Tolstikov, I.V. Chudov, G.V. Bazekin, A.F. Ismagilova, 2010, published in Bioorganicheskaya Khimiya, 2010, Vol. 36, No. 2, pp. 277–282.

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Kazakova, O.B., Tret’yakova, E.V., Smirnova, I.E. et al. The synthesis and anti-inflammatory activity of quinopimaric acid derivatives. Russ J Bioorg Chem 36, 257–262 (2010).

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Key words

  • anti-inflammatory activity
  • Beckman rearrangement
  • diene adducts
  • lactams
  • levopimaric acid
  • oximes
  • quinopimaric acid
  • toxicity