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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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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