Pecularities of 16-nitro- and 16-amino-14,17-ethanosteroids preparation in the estrane series

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

The hydrogenation of 16-nitro-14,17-ethenosteroids over various catalysts was studied, chemoselectivity criteria have been established, new bridged estradiol analogs bearing nitro, amino and hydroxylamino groups in the D ring have been prepared. A complete assignment of signals in the NMR spectra of the synthesized products was fulfilled

About the authors

A. V Baranovsky

Institute of bioorganic chemistry of the National Academy of Sciences

Email: baranovsky@iboch.by

A. S Ladyko

Institute of bioorganic chemistry of the National Academy of Sciences

S. N Sokolov

Institute of bioorganic chemistry of the National Academy of Sciences

References

  1. Kirsch G., Neef G., Laurent H., Wiechert R., Beier S., Elger W., Bull J.R. Пат. DE 3838779 A1 (1990). ФРГ. C.A. 1990, 113, 231776.
  2. Laurent H., Esperling P., Krattenmacher R., Elger W. Пат. DE 4114635 A1 (1992). ФРГ. C.A. 1993, 118, 124872
  3. Kirsch G., Neef G., Laurent H., Wiechert R., Bull J.R., Elger W., Beier S. Пат. DE 3939894 (1991). ФРГ. C.A. 1991, 115, 136493.
  4. Bull J.R., Elger W., Fritzemeier K.-H., Krattenmacher R. Пат. EP 511727 A1 (1992). Евр. C.A. 1993, 118, 124871.
  5. Bohlmann R., Kuenzer H., Wiechert R., Henderson D., Schneider M., Nishino Y. Пат. US 5145847 (1992). США. C.A. 1991, 115, 29717.
  6. Leysen D., Cals J.M.G.B. Пат. WO 03053993 A1 (2003). Межд. C.A. 2003, 139, 69427.
  7. Schoellkopf K., Halfbrodt W., Kuhnke J., Schwede W., Fritzemeier K.-H, Drattenmacher R., Muhn H.-P. Пат. DE 4447401 A1 (1996). ФРГ. C.A. 1996, 125, 143131.
  8. Baranovsky A.V., Bolibrukh D.A., Bull J.R. Eur. J. Org. Chem. 2007, 445-454. doi: 10.1002/ejoc.200600629.
  9. Baranovsky A.V., Bolibrukh D.A., Schneider B. Steroids. 2015, 104, 37-48. doi: 10.1016/j.steroids.2015.08.009.
  10. Барановский А.В., Бильдюкевич В.Н., Голубева М.Б., Кузьмицкий Б.Б., Мамчиц Ю.Ю. Биоорг. хим. 2016, 42, 94-103.
  11. Baranovsky A.V., Bil'dyukevich V.N., Golubeva M.B., Kuzmitsky B.B., Mamchits Yu.Yu. Russ. J. Bioorg. Chem. 2016, 42, 83-92. doi: 10.1134/S1068162015060023
  12. Kirsch G., Neef G., Lauren, H., Wiechert R., Bull J R., Esperling P., Elger W., Beier S. Пат. EP 430386 A1 (1991), Евр. C.A. 1991, 115, 136493.
  13. Pataki J., Siade G. J. Org. Chem. 1972, 37, 2127-2131. doi: 10.1021/jo00978a014
  14. Dayal B., Ertel N.H., Rapole KR., Asgaonkar A., Salen G. Steroids. 1997, 62, 451-454. doi: 10.1016/S0039-128X(97)00010-X
  15. Ram S., Ehrenkaufer R.E. Tetrahedron Lett. 1984, 25, 3415-3418. doi: 10.1016/S0040- 4039(01)91034-2
  16. Buchanan J.G., Flinn A., Mundill P.H.C., Wightman R.H. Nucleosides Nucleotides. 1986, 5, 313-323. doi: 10.1080/07328318608069980
  17. Armarego W.L.F., Chai C.L.L Purification of Laboratory Chemicals. 5th Ed. Oxford: Butterworth- Heinemann. 2003.
  18. Барановский А.В., Ладыко А.С., Шатская В.А., Щербаков А.М. ЖОрХ. 2019, 55, 252-265
  19. Russ. J. Org. Chem. 2019, 55, 202-214. doi: 10.1134/S107042801902012X

Supplementary files

Supplementary Files
Action
1. JATS XML

Copyright (c) 2023 Russian Academy of Sciences