Antihormonal properties of some new A-homo-B, 19-dinor steroids of the androstane series.
On solvolysis of Westphalen-type steroids with a leaving group in the position 6 beta (e.g., 2), products of elimination (followed by rearrangement and fragmentation of the steroid skeleton) were prepared (e.g., 4 and 5). These products were subsequently converted to suitable analogs of the compound, which has been reported to promote hair growth (1). Compounds 11 to 13 exhibited strong antiandrogenic activity in vivo; however, this activity could not be interpreted either in terms of inhibition of 5 alpha-reductase or by strong binding to an androgen receptor.
Kasal
A
A
Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, Prague.
Hampl
R
R
Bicíková
M
M
Stárka
L
L
D000726:Androgen Antagonists / Q000378:metabolism / Q000494:pharmacology*; D059002:Androgen Receptor Antagonists; D015114:Androstenediol / Q000031:analogs & derivatives*; D000734:Androstenediols / Q000378:metabolism / Q000494:pharmacology*; D000736:Androstenes / Q000378:metabolism / Q000494:pharmacology*; D000818:Animals; D001681:Biological Assay; D042944:Cholestenone 5 alpha-Reductase; D008297:Male; D051379:Mice; D015394:Molecular Structure; D010088:Oxidoreductases / Q000378:metabolism; D011944:Receptors, Androgen / Q000378:metabolism; D012632:Secosteroids
D000726:Androgen Antagonists; D059002:Androgen Receptor Antagonists; D000734:Androstenediols; D000736:Androstenes; D011944:Receptors, Androgen; D012632:Secosteroids; C078541:3-acetoxy-4a-methyl-A-homo-B,19-dinor-3,4-secoandrost-9-en-17-one; C078543:4a-methylene-17-methyl-A-homo-B,19-dinorandrost-9-ene-3,17-diol; C078542:4a,17-dimethyl-A-homo-B,19-dinor-3,4-secoandrost-9-ene-3,17-diol; D015114:Androstenediol; D010088:Oxidoreductases; D042944:Cholestenone 5 alpha-Reductase