INFLUENCE OF MOLECULAR UNSATURATION ON HORMONAL ACTIVITY PATTERN OF CERTAIN HETEROCYCLIC STEROIDS

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Abstract
The pattern of hormonal activity in rats of [3,2-c] pyrazole derivatives of steroids was profoundly altered by minor changes in the degree of unsaturation of the steroidal moiety. 17α-Hydroxy-17α-methylandrostano [3,2-c] pyrazole induced marked retention of nitrogen, was myotrophic and weakly androgenic. The singly unsaturated steroid derivative, 17β-hydroxy-17α-methylandrost-4- eno [3,2-c] pyrazole, did not promote nitrogen retention, although it was myotrophic, weakly androgenic and estrogenic. The doubly unsaturated steroid derivative, 17β-hydroxy-17α-methylandrosta-4,6-dieno [3,2-c] pyrazole, was typically estrogenic without anabolic or androgenic activities. The activity patterns of these heterocyclic steroids were compared with those of the corresponding parent steroids: 17α-methylandrostane-17β-ol-3-one, 17a-methylandrost- 4-ene-17β-ol-3-one and 17α-methylandrosta-4,6-diene-17β-ol-3-one. The degree of unsaturation of the parent steroids was observed to alter the magnitude but not the kind of hormonal activity. These structure-activity relationships are discussed with reference to known physical chemical features of the various steroids.

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