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DOI: 10.1039/A904410H (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1999, 2089-2092

NMR and conformational studies of the antimalarial drug arte-ether

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Anthony R. Butler, Laura Conforti, Philippa Hulme, Louise M. Renton and Trevor J. Rutherford

Abstract

The 1H and 13C NMR spectra of the antimalarial drug arte-ether (a derivative of qinghaosu) have been obtained and stereospecific assignments made using standard one- and two-dimensional techniques. Proton homonuclear spin-coupling constants were quantified from J-resolved and E.COSY experiments and confirmed that the solution conformation of arte-ether is similar to that of the reported crystal structure of artmether. A conformational model was generated using AM1 semi-empirical energy calculations, and was consistent with both the measured spin-coupling constants and experimental NOE data.

References

  1. D. L. Klayman, Science, 1985, 228, 1049 CrossRef CAS.
  2. Qinghao Antimalarial Coordinating Research Group, Chin. Med., 1979, 92, 811 Search PubMed.
  3. A. R. Butler and Y.-L. Wu, Chem. Soc. Rev., 1992, 85 RSC.
  4. G. Blaskó, G. A. Cordell and D. C. Lankin, J. Nat. Prod., 1988, 51, 1273 CrossRef.
  5. A. R. Butler, L. Conforti, B. C. Gilbert and A. C. Whitwood, unpublished data.
  6. A. Brossi, B. Venugolplan, L. Dominguez Gerpe, H. J. C. Yeh, J. L. Flippen-Anderson, P. Bucks, X. D. Luo, W. Milhous and W. Peters, J. Med. Chem., 1988, 31, 645 CrossRef CAS.
  7. M. Jung, X. Li, D. A. Bustros, H. N. El-Sohly, J. D. McChesney and W. K. Milhous, J. Med. Chem., 1990, 33, 1516 CrossRef CAS.
  8. W. M. Wu, Z. L. Yao, Y. L. Wu, K. Jiang, Y. F. Wang, H. B. Chen, F. Shan and Y. Li, Chem. Commun., 1996, 2213 RSC.
  9. A. R. Butler, B. C. Gilbert, P. Hulme, L. R. Irvine, L. Renton and A. C. Whitwood, Free Radical Res., 1998, 28, 471 Search PubMed.
  10. N. Acton and D. L. Klayman, Planta Med., 1985, 441 CAS.
  11. F. S. El-Feraly, M. M. El-Sherei, C. D. Hufford, E. M. Croom and T. J. Mashier, Spectrosc. Lett., 1985, 18, 843 CAS.
  12. W. Zhongshan, T. T. Nakashima, K. R. Kopecky and J. Molina, Can. J. Chem., 1985, 63, 3070.
  13. J.-J. Huang, K. M. Nicholls, C.-H. Chang and Y. Wang, Acta Chem. Sin., 1987, 45, 305 Search PubMed.
  14. O. Prakash, R. Roy, R. S. Kapil and R. A. Vishwakarma, Ind. J. Chem., 1990, 29B, 103 Search PubMed.
  15. L. N. Misra, A. Ahmad, R. S. Thakur, H. Lotter and H. Wagner, J. Nat. Prod., 1993, 56, 215 CrossRef CAS.
  16. X.-d. Luo, H. J. C. Yeh, A. Brossi, J. L. Flippen-Anderson and R. Gilardi, Helv. Chim. Acta, 1984, 67, 1515 CrossRef CAS.
  17. C. A. G. Haasnoot, F. A. A. M. de-Leeuw and C. Altona, Bull. Soc. Chim. Belg., 1980, 89, 125 CAS.
  18. C. Griesinger, O. W. Sθrensen and R. R. Ernst, J. Am. Chem. Soc., 1985, 107, 6394 CrossRef CAS.
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