7 alpha-Alkyltestosterone derivatives: synthesis and activity as androgens and as aromatase inhibitors.
The 7 alpha-ethyl,propyl,butyl,3'-t-butoxypropyl,allyl,3'-hydroxypropyl 17-acetate, and 3'-chloropropyl 17-acetate derivatives of testosterone and the 7 alpha-3'-t-butoxypropyl, 3'-hydroxypropyl,3'-acetoxypropyl,3'-bromoacetoxypropyl, 3'-chloropropyl, and 2'-oxo-3'-bromopropyl derivatives of 4-androstene-3,17-dione were synthesized. The testosterone derivatives were found to lose androgenic and anabolic activity rapidly as the size of the group at the 7 position increased. Many of the compounds were tested as inhibitors of aromatase. The 17-keto compounds were more active than the corresponding alcohols and the enzyme was found to tolerate at least the bulk of a hydroxypropyl group at the C-7 alpha position.
D000728:Androgens / Q000138:chemical synthesis*; D000818:Animals; D047072:Aromatase Inhibitors; D001681:Biological Assay; D002369:Castration; D007202:Indicators and Reagents; D008297:Male; D009929:Organ Size / Q000187:drug effects; D010088:Oxidoreductases / Q000037:antagonists & inhibitors*; D011467:Prostate / Q000187:drug effects; D051381:Rats; D012669:Seminal Vesicles / Q000187:drug effects; D013329:Structure-Activity Relationship; D013739:Testosterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000728:Androgens; D047072:Aromatase Inhibitors; D007202:Indicators and Reagents; D013739:Testosterone; D010088:Oxidoreductases