Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Isolation and Structural Elucidation of Related Impurities in Canrenone

  • Yang, Ya-Xi (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology) ;
  • Chen, Guo-Rong (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology)
  • Published : 2009.10.20
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Abstract

Ten steroidal compounds as impurities in canrenone were isolated from the enriched mother liquor by using various chromatographic methods. Their structures were elucidated by spectrometric analysis, among which three new compounds were characterized as 3-(3-oxo-7$\alpha$-(ethoxycarbonyl)methyl-17$\beta$-hydroxy-4-androsten-17$\alpha$-yl) propionic acid $\gamma$-lactone (1), 3-(3-oxo-7$\alpha$-ethoxy-17$\beta$-hydroxy-4-androsten-17$\alpha$-yl) propionic acid $\gamma$-lactone (2) and 3-(3-oxo- 5$\beta$-propionic acid-$\gamma$-lactone-6$\beta$,17$\beta$-hydroxy-4-androstan-17$\alpha$-yl) propionic acid $\gamma$-lactone (3).

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References

  1. Sadee, W.; Dagcioglu, M.; Schroder, R. J. Pharmacol. Exp. Ther. 1973, 185, 686.
  2. Jackson, E. K. Goodman and Gilman's The Pharmacological Basis of Therapeutics; McGraw-Hill: New York, U. S. A., 2006; Vol. 11, p 737.
  3. Spark, R. F.; Melby, J. C. Ann. Intern. Med. 1971, 75, 831. https://doi.org/10.7326/0003-4819-75-6-831
  4. Brest, A. N. Clin. Ther. 1986, 8, 568.
  5. de Gasparo, M. J. Pharmacol. Exp. Ther. 1987, 240, 650.
  6. McMahon, E. G. Curr. Opin. Pharmacol. 2001, 1, 190. https://doi.org/10.1016/S1471-4892(01)00022-4
  7. Wuts, P. G. M.; Ritter, A. R. J. Org. Chem. 1989, 54, 5180. https://doi.org/10.1021/jo00282a041
  8. Zhang, Y. H.; Xiong, Z. G. Chinese Journal of Medicinal Chemistry 2005, 15, 241.
  9. David, L.; Raginald, L. WO 9428904, 1994.
  10. Karim, A.; Brown, E. A. Steroids 1972, 20, 41. https://doi.org/10.1016/0039-128X(72)90117-1
  11. James, R. H.; Michael, S. J. Chem. Soc. (Perkin І) 1975, 1956.
  12. Daniel, M. T. Steroids 1989, 54, 113. https://doi.org/10.1016/0039-128X(89)90078-0
  13. Sam, K. M.; Serge, A.; Van, L. T.; Donald, P. J. Med. Chem. 1995, 38, 4518. https://doi.org/10.1021/jm00022a018
  14. Palem-Vliers, M.; Genard, P.; Hacha, R. Archives Internationales de Physiologie et de Biochimi 1987, 95, 373. https://doi.org/10.3109/13813458709113149
  15. Fieser, L.; Fieser, M. Steroids; Reinhold Publishing Corp: New York, U. S. A., 1959; p 530.