Chemistry of Natural Compounds

, Volume 15, Issue 4, pp 435–441 | Cite as

Synthesis and study of hydrazones of 17α-hydroxyprogesterone and 17α-hydroxypregna-4,6-diene-3,20-dione and their 17α-acylated derivatives

  • L. N. Volovel'skii
  • I. B. Skachek
  • A. G. Selichenko
  • I. I. Kuz'menko
Article
  • 32 Downloads

Abstract

It has been shown that under mild conditions the reactions of 17α-hydroxy 3,20-diones of the pregnane series with acid hydrazides lead to the formation of 3-monohydrazones, while under severe conditions 3,20-dihydrazones are formed regardless of whether a C4–C5 ethylenic bond or a chain of conjugation of C4–C5 and C6–C7 ethylenic bonds is present in the steroid molecule. The reaction of 17α-acetoxy 3,20-diketones of the pregnane series with acid hydrazides takes place only with the formation of 3-monohydrazones. An investigation of the gestagenic action of some of the compounds synthesized has shown that the presence of a 3-keto group in the steroids of the pregnane series is not necessary for the retention of this effect. The replacement of the keto group at carbon atom 3 by an azomethine group does not abolish the gestagenic action.

Keywords

Pregnane Acid Hydrazide Isonicotinic Acid Azomethine Group Ethylenic Bond 

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Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • L. N. Volovel'skii
  • I. B. Skachek
  • A. G. Selichenko
  • I. I. Kuz'menko

There are no affiliations available

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