Abstract
D-Homo derivatives in the androstane and estrane series, 12-19, were synthesized by a fragmentation-cyclization reaction of 16-oximino-17-hydroxy-17-substituted derivatives 3-9, or by cyclization of the corresponding D-seco derivatives 20-26. The structures were confirmed by X-ray analysis of compounds 12 and 16. Preliminary assessment of inhibitory effects of D-homo derivatives from androstane series towards aromatase, 3 beta-hydroxysteroid dehydrogenase (3 beta-HSD), 17 alpha-hydroxylase/C17-20 lyase (P450c17) and 17 beta-HSD indicated much lower inhibitory potential compared to previously tested activity of another type of D-modified steroids, namely D-seco derivatives. Also, assessment of potential antiestrogenic activity of derivatives from estrane series showed absence of such an activity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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17-Hydroxysteroid Dehydrogenases / antagonists & inhibitors
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3-Hydroxysteroid Dehydrogenases / antagonists & inhibitors
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Androstenes / chemistry
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Androstenes / pharmacology
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Animals
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Aromatase Inhibitors
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Crystallography, X-Ray*
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / pharmacology
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Estranes / chemistry
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Estranes / pharmacology
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Estrogen Receptor Modulators / chemical synthesis
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Estrogen Receptor Modulators / chemistry
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Estrogen Receptor Modulators / pharmacology
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Homosteroids / chemical synthesis*
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Homosteroids / chemistry
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Homosteroids / pharmacology
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Leydig Cells / enzymology
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Male
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Molecular Structure
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Rats
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Steroid 17-alpha-Hydroxylase / antagonists & inhibitors
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Structure-Activity Relationship
Substances
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Androstenes
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Aromatase Inhibitors
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Enzyme Inhibitors
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Estranes
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Estrogen Receptor Modulators
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Homosteroids
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17-Hydroxysteroid Dehydrogenases
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3-Hydroxysteroid Dehydrogenases
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Steroid 17-alpha-Hydroxylase