Synthesis and study of hydrazones of 17α-hydroxyprogesterone and 17α-hydroxypregna-4,6-diene-3,20-dione and their 17α-acylated derivatives
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.
KeywordsPregnane Acid Hydrazide Isonicotinic Acid Azomethine Group Ethylenic Bond
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- 1.L. Fieser and M. Fieser, Steroids, Reinhold, New York (1959).Google Scholar
- 2.P. de Ruggieri, C. Landofi, and D. Chiaramonti, Bull. Soc. Ital. Biol. Sperim.,38, 985 (1962).Google Scholar
- 4.G. Stevens, US Patent No. 3,169,979 of Feb. 16, 1965.Google Scholar
- 5.L. M. Makarevich-Gal'perin, S. N. Ushenko, and L. N. Volovel'skii, Proceedings of the Kharkov Scientific-Research Institute of Endocrinology and Hormone Chemistry [in Russian] (1965), p. 291.Google Scholar
- 6.L. M. Makarevich-Gal'perin and S. N. Ushenko, Pharmacology and Toxicology. Republican Interdepartmental Symposium [in Russian], No. 10 (1975), pp. 73–76.Google Scholar
- 7.L. N. Volovel'skii, Ukr. Khim. Zh.,23, 72 (1957).Google Scholar
- 8.L. N. Volovel'skii, Zh. Obshch. Khim.,37, 590 (1967).Google Scholar
- 10.L. Bellamy, Infrared Spectra of Complex Molecules, 2nd ed., Methuen, London/Wiley, New York (1958).Google Scholar