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Study by NMR Spectroscopy of Particular Spatial Structure of B,19-Bisnortestosterone 9,10-Isoanalogs

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Abstract

For two isoanalogs of B,19-bisnortestosterone was carried out a complete assignment of signals in the 1H and 13C NMR spectra with the help of homonuclear and heteronuclear correlation NMR spectroscopy. The predominant conformations of the substances in solutions were derived from the values of coupling constants and nuclear Overhauser effect data.

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REFERENCES

  1. Falkenstein, E., Tillmann, H., Christ, M., Feuring, M., and Wehling, M., Pharmacol. Rev. 2000, vol. 52, pp. 513-555.

    Google Scholar 

  2. Levin, E.R., Trends in Endocrinology and Metabolism 1999, vol. 10, no. 9, pp. 374-377.

    Google Scholar 

  3. Chen, H.C. and Farese, Jr. R.V., Current Biology 1999, vol. 9, no. 13, pp. 478-481.

    Google Scholar 

  4. RCT Int. Appl., WO 99 46.279. Chem. Abstr. 1999, vol. 131, R228876kh.

  5. Romer, W., Oettel, M., and Schwarz, S., Can. J. Physiol. Chem. 1998, vol. 76, pp. 99-109.

    Google Scholar 

  6. RCT Int. Appl. WO 00 07.576, Chem. Abstr. 2000 vol. 132, 152024t.

  7. RCT Int. Appl. WO 99 58550, Chem. Abstr. 1999, vol. 131, 351534r.

  8. Katsapova, O.F., Krylova, E.B., Martynov, V.F., and Shavva, A.G., Zh. Obshch. Khim. 1981, vol. 51, no. 12, pp. 2797-2799.

    Google Scholar 

  9. US Patent 3354183, 1967. Ref. Zh. Khim. 1969, 11N426P.

  10. Sorokina, I.B., Barkova, T.I., Zakharychev, A.A., Chigir', R.N, Ananchenko, C.N., and Torgov, I.V., Izv. Akad. Nauk SSSR Ser. Biol., 1973, no. 5, pp. 664-670.

  11. Egorov, M.C., Grinenko, E.V., Zorina, A.D., Balykina, L.V., Celivanov, C.I., and Shavva, A.G., Zh. Org. Khim. 2001, vol. 37, no. 6, pp. 849-857.

    Google Scholar 

  12. Burckhalter, J.H. and Sciavolino, F.C., J. Org. Chem. 1967, vol. 32, no. 12, pp. 3968-3973.

    Google Scholar 

  13. Heidepriem, H., Rufer, C., Kosmol, H., Schroder, E., and Kieslich K., Ann. Chem. 1968, vol. 712, pp. 155-167.

    Google Scholar 

  14. Karplus, M., J. Am. Chem. Soc. 1963, vol. 85, p. 2870.

    Google Scholar 

  15. Derome, A.E., Modern NMR Techniques for Chemistry Research New York: Pergamon Books Ltd., 1987.

    Google Scholar 

  16. Neuhaus, D. and Williamson, M.P., The Nuclear Overhauser Effect in Structural and Conformational Analysis New York: VCH Publishers, Inc., 1989.

    Google Scholar 

  17. Piantini, U., Sorensen, O.W., and Ernst, R.R., J. Am. Chem. Soc. 1982, vol. 104, pp. 6800-6801.

    Google Scholar 

  18. Bodenhausen, G. and Ruben, D.J., Chem. Phys. Lett. 1980, vol. 69, pp. 185-189.

    Google Scholar 

  19. Reynolds, W.F., McLean, S., Tay, L.-L., Enriquez, Yu.R., Estwick, D.M., and Pascoe, K.O., Magn. Res. Chem. 1997, vol. 35, pp. 455-462.

    Google Scholar 

  20. Macura, S. and Ernst, R.R., Mol. Phys. 1980, vol. 41, pp. 95-117.

    Google Scholar 

  21. Schroder, H. and Haslinger, E., Magn. Res. Chem. 1994, vol. 32, pp. 12-15.

    Google Scholar 

  22. Keeler, J., Neuhaus, D., and Williamson, M.P., J. Magn. Res. 1987, vol. 73, pp. 45-68.

    Google Scholar 

  23. Simova, S., Magn. Res. Chem. 1998, vol. 36, pp. 505-510.

    Google Scholar 

  24. Imai, K. and Osawa, E., Tetrahedron Lett. 1989, vol. 30, no. 32, pp. 4251-4254.

    Google Scholar 

  25. Landy, S.B. and Rao, B.D.N., J. Magn. Res. 1989, vol. 83, pp. 29-43.

    Google Scholar 

  26. Andersen, N.H., Eaton, H.L., and Lai, X., Magn. Res. Chem. 1989, vol. 27, pp. 515-528.

    Google Scholar 

  27. Lane, A.N., J. Magn. Res. 1988, vol. 78, pp. 425-429; Borgias, B.A., Gochin, M., Kerwood, D.J., and James, T.L., Prog. NMR Spectrosc. 1990, vol. 22, pp. 83-100.

    Google Scholar 

  28. Lai, X., Reid, B., and Andersen, N.H., J. Magn. Res. 1993, Ser. B, vol. 101, pp. 289-293.

    Google Scholar 

  29. Selivanov, S.I., Tsogoeva, S.B., Starova, G.L., and Shavva, A.G., Proceedings of 30th Congress AMPEREMagnetic Resonance and Related Phenomena,” Lisbon, 2000, p. 120.

  30. Woessner, D.E., J. Chem. Phys. 1962, vol. 17, no. 3, pp. 647-654.

    Google Scholar 

  31. Withka, J.M., Swaminathan, S., and Bolton, P.H., J. Magn. Res. 1990, vol. 89, pp. 386-390.

    Google Scholar 

  32. Maes, D., Cauteran, M.V., Wyns, L., Lisgarten, J., Palmer, R., Lisgarten, D., Willem, R., Biesemans, M., and Kayser, F., J. Chem. Soc., Perkin Trans. 1992, no. 2, pp. 2179-2185.

  33. Kayzer, F., Maes, D., Wyns, l., Lisgarten, J., Palmer, R., Lisgarten, D., Willem, R., Martins, J.C., Verheyden, P., and Biesemans, M., Steroids 1995, vol. 60, pp. 713-719.

    Google Scholar 

  34. Peterson, P.E. and Chevli, D.M., J. Org. Chem. 1974, vol. 39, no. 25, pp. 3684-3691.

    Google Scholar 

  35. Egorova, V.V., Zakharychev, A.V., and Ananchenko, S.N., Tetrahedron 1973, vol. 29, pp. 301-307.

    Google Scholar 

  36. Rao, G.S.R. Subba and Sundar, N.Sh., Indian J. Chem. 1988, vol. 15B, no. 7, pp. 585-588.

    Google Scholar 

  37. Lindon, J.C. and Ferrige, A.G., Prog. NMRSpectrosc. 1982, vol. 14, p. 27.

    Google Scholar 

  38. Shaka, A.J., Keeler, J., and Freeman, R., J. Magn. Res. 1983, vol. 53, no. 2, pp. 313-340.

    Google Scholar 

  39. Shaka, A.J. and Keeler, J., Prog. NMR Spectrosc. 1987, vol. 19, no. 1, pp. 47-129

    Google Scholar 

  40. Bodenhausen, G., Vold, R.L., and Vold, R.R., J. Magn. Res. 1980, vol. 37, p. 93.

    Google Scholar 

  41. Reynolds, W.F., Yu, M., Enriquez, R.G., and Leon, I., Magn. Res. Chem. 1997, vol. 35, pp. 505-519.

    Google Scholar 

  42. Geppert, T., Kock, M., Reggelin, M., and Griesinger, C., J. Magn. Res. 1995, Ser. B, vol. 107, pp. 91-93.

    Google Scholar 

  43. Wang, K.Y., Borer, P.N., Levy, G.C., and Pelczer, I., J Magn. Res. 1992, vol. 96, pp. 165-170.

    Google Scholar 

  44. Rzheznikov, V.M., Ananchenko, C.N., and Torgov, I.V., Khim. Polimer. Soed. 1965, no. 2, pp. 90-100.

  45. Krylova, E.B., Martynov, V.F., and Shavva, A.G., Zh. Org. Khim. 1978, vol. 14, no. 12, pp. 2518-2523.

    Google Scholar 

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Egorov, M.S., Selivanov, S.I. & Shavva, A.G. Study by NMR Spectroscopy of Particular Spatial Structure of B,19-Bisnortestosterone 9,10-Isoanalogs. Russian Journal of Organic Chemistry 38, 200–209 (2002). https://doi.org/10.1023/A:1015557431599

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