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

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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.

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Authors
  1. L. N. Volovel'skii
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  2. I. B. Skachek
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  3. A. G. Selichenko
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  4. I. I. Kuz'menko
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Additional information

Kharkov Scientific-Research Institute of Endocrinology and Hormone Chemistry. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 501–509, July–August, 1979.

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Volovel'skii, L.N., Skachek, I.B., Selichenko, A.G. et al. Synthesis and study of hydrazones of 17α-hydroxyprogesterone and 17α-hydroxypregna-4,6-diene-3,20-dione and their 17α-acylated derivatives. Chem Nat Compd 15, 435–441 (1979). https://doi.org/10.1007/BF00565041

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  • DOI: https://doi.org/10.1007/BF00565041

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