Skip to main content
SpringerLink
Log in

Synthesis of Several 5α-Androstano[17,16-d]Pyrazolines from Tigogenin

  • Published:
Chemistry of Natural Compounds Aims and scope

New androstanopyrazolines and hydrazones were synthesized via acid-catalyzed condensation of the tigogenin transformation product 5α-pregnenolone with several hydrazines. Their structures were proved using IR and NMR spectroscopy and mass spectrometry. An x-ray crystal structure analysis was performed for pregnenolone p-nitrophenylhydrazone acetate.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. I. V. Zavarzin, A. V. Kamernitsky, V. V. Chertkova, E. I. Chernoburova, V. N. Yarovenko, M. M. Kraushkin, and V. V. Kachala, ARKIVOC, IV, 62 (2008).

    Article  Google Scholar 

  2. Shamsuzzaman, H. Khanam, A. Mashrai, A. Sherwani, M. Owais, and N. Siddiqui, Steroids, 78, 1263 (2013).

    Article  CAS  PubMed  Google Scholar 

  3. Shamsuzzaman, M. S. Khan, and M. Alam, J. Chil. Chem. Soc., 54 (4), 372 (2009).

    Article  CAS  Google Scholar 

  4. A. H. Banday, B. P. Mir, I. H. Lone, K. A. Suri, and H. M. S. Kumar, Steroids, 75, 805 (2010).

    Article  CAS  PubMed  Google Scholar 

  5. A. V. Kamernitskii, E. I. Chernoburova, V. V. Chertkova, I. V. Zavarzin, V. N. Yarovenko, and M. M. Krayushkin, Bioorg. Khim., 33 (3), 337 (2007).

    CAS  PubMed  Google Scholar 

  6. M. I. Merlani, E. P. Kemertelidze, K. Papadopulos, and N. I. Men’shova, Bioorg. Khim., 30 (5), 552 (2004).

    CAS  PubMed  Google Scholar 

  7. A. E. Amr, N. A. Abdel-latif, and M. M. Abdalla, Bioorg. Med. Chem., 14, 373 (2006).

    Article  CAS  Google Scholar 

  8. M. I. Sikharulidze, N. Sh. Nadaraia, M. L. Kakhabrishvili, N. N. Barbakadze, and K. G. Mulkidzhanyan, Chem. Nat. Compd., 46, 493 (2010).

    Article  CAS  Google Scholar 

  9. M. I. Sikharulidze, N. Sh. Nadaraia, and M. L. Kakhabrishvili, Chem. Nat. Compd., 48, 423 (2012).

    Article  CAS  Google Scholar 

  10. N. I. Men’shova, N. A. Korzinkina, E. P. Kemertelidze, N. Sh. Nadaraia, M. G. Davitishvili, L. I. Lishcheta, and V. S. Grosheva, Sb. Nauchn. Tr. VNIFKhI, 10, 83b (1982).

    Google Scholar 

  11. J. B. Cazaux, R. Jacquier, and G. Maury, Tetrahedron Lett., 1, 41 (1971).

    Article  Google Scholar 

  12. A. V. Kamernitsky, E. I. Chernoburova, V. V. Chertkova, V. N. Yarovenko, I. V. Zavarzin, and M. M. Krayushkin, Russ. Chem. Bull., 55 (11), 2117 (2006).

    Article  Google Scholar 

  13. Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow, 1974, 191 pp.

    Google Scholar 

  14. Oxford Diffraction, CrysAlisPro, Oxford Diffraction Ltd., Yarnton, England, 2009.

  15. G. M. Sheldrick, Program for Empirical Absorption Correction of Area Detector Data, University of Goettingen, Goettingen, 1996.

    Google Scholar 

  16. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 64, 112 (2008).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. I. Kutateladze Institute of Pharmaceutical Chemistry, Tbilisi State Medical University, Tbilisi, 0159, Georgia

    N. Sh. Nadaraia, M. L. Kakhabrishvili, E. O. Onashvili, N. N. Barbakadze, M. Z. Getia & M. I. Sikharulidze

  2. LASEVE, Universite Quebec a Chicoutimi, Chicoutimi, QC, Canada, G7H 2B1

    M. Z. Getia & A. Pichette

  3. S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences, Republic of Uzbekistan, Tashkent

    U. S. Makhmudov

Authors
  1. N. Sh. Nadaraia
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. L. Kakhabrishvili
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. O. Onashvili
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. N. Barbakadze
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. Z. Getia
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. Pichette
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. M. I. Sikharulidze
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. U. S. Makhmudov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. Sh. Nadaraia.

Additional information

M. I. Sikharulidze is deceased.

Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2014, pp. 890–894.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nadaraia, N.S., Kakhabrishvili, M.L., Onashvili, E.O. et al. Synthesis of Several 5α-Androstano[17,16-d]Pyrazolines from Tigogenin. Chem Nat Compd 50, 1024–1028 (2014). https://doi.org/10.1007/s10600-014-1151-1

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-014-1151-1

Keywords

Search

Navigation