Skip to main content
SpringerLink
Log in

New variants in the total synthesis of 14β-hydroxy-17α,R-8α,9β-estradiol derivatives

  • Chemistry of Natural Compounds and Bioorganic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Two procedures were developed for the synthesis of 17α-alkyl-8α,9β-estra-1,3,5(10)-triene-3,14β,17β-triols from 3-methoxy-estra-1,3,5(10),8(9),14(15)-pentaene-17-one (1) using photosensitized oxidation by atmospheric oxygen or ionic hydrogenation in the presence of oxygen. It was shown that 17α-hexynyl-8α,9β-estra-1,3,5(10)-triene-3,14β,17β-triol (23) and its 3-methoxy derivative (26) inhibit K+,Na+-ATPase, with inhibition degree increasing on introduction of an oxygen-containing substituent into position 17. For the first time steroids were found with α2-adrenoblocking action.

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

Similar content being viewed by others

References

  1. A.V.Platonova, A.O.Layliev, S.N.Ananchenko, and I.V.Torgov,Bioorg.Khim, 1982,8, 542 [Sov.J.Bioorg.Chem.].

    Google Scholar 

  2. V.I.Zaretsky, inMass Spectrometry of Steroids, Israel University Press, New York, Toronto, 1976, 81.

    Google Scholar 

  3. T.R.Kasturi and J.Parvathis,J.Chem.Soc. Perkin Trans.1, 1980, 448.

    Google Scholar 

  4. W.A.Ayer, J.M.Browne, and S.Fung,Can.J.Chem., 1976,54, 3276; K.Gollnik and J.Schade,Tetrahedron Lett., 1966, 2335; A.R.Bell, R.E.Ireland, and L.N.Mandec,J.Org.Chem., 1966,31, 2536.

    Google Scholar 

  5. M.V.Dodonov, N.S.Pestovsky, and S.N.Ananchenko,Proc. VII Indo-Soviet Symposium on the Chemistry of Natural Products, 8–12 December, 1986, 48.

  6. G.A.Serebryakova, A.V.Zakharychev, S.N.Ananchenko, Z.N.Parnes, and I.V.Torgov,Izv.Akad. Nauk SSSR. Ser.Khim., 1969, 725 [Bull.Acad.Sci USSR. Div.Chem.Sci., 1969].

  7. N.S.Wulfson, V.I.Zaretskii, V.Z.Sadovskaya, A.V.Zakharychev, S.N.Ananchenko, and I.V.Torgov,Tetrahedron, 1967,23, 3667.

    Google Scholar 

  8. V.I.Zaretskii, N.S.Wulfson, V.G.Zaikin, S.N.Ananchenko, V.Leonov, and I.V.Torgov,Tetrahedron, 1965,21, 2469.

    Google Scholar 

  9. M.Kh.Dzhafarov and T.V.Timofeeva,5th All-Union Meeting on Organic Crystallochemistry, 1991, Kiev, p.73.

  10. G.G.Vasiyarov and S.N.Ananchenko,Izv.Akad. Nauk SSSR. Ser.Khim, 1975, 196 [Bull.Acad.Sci USSR. Div.Chem.Sci., 1975, No. 1].

Download references

Author information

Authors and Affiliations

  1. M.M.Shemyakin Institute of Bioorganic Chemistry, Russian Academy of Sciences, 117871, Moscow, Russian Federation

    S. Kh. Karamyan, S. N. Ananchenko & M. Kh. Dzhafarov

Authors
  1. S. Kh. Karamyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. N. Ananchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Kh. Dzhafarov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 207–212, January, 1993.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Karamyan, S.K., Ananchenko, S.N. & Dzhafarov, M.K. New variants in the total synthesis of 14β-hydroxy-17α,R-8α,9β-estradiol derivatives. Russ Chem Bull 42, 189–193 (1993). https://doi.org/10.1007/BF00700007

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00700007

Key words

Search

Navigation