Synthesis and anabolic/androgenic evaluation of novel 9alpha-fluorosteroids.
3Beta,11beta-dihydroxy-9alpha-fluor-5alpha-androstane-17-one (2), 3beta-acetoxy-9alpha-fluor-11beta-hydroxy-5alpha-androstane-17-one (3), 3beta-acetoxy-9alpha-fluor-11beta,17beta-dihydroxy-5alpha-androstane (4), 3beta,17beta-diacetoxy-9alpha-fluor-11beta-hydroxy-5alpha-androstane (5), 3beta-acetoxy-9alpha-fluor-11beta-hydroxy-5alpha-androstane 17beta-propionate (6), 3beta-acetoxy-9alpha-fluor-11beta-hydroxy-5alpha-androstane 17beta-enanthate (7), 3beta-acetoxy-9alpha-fluor-11beta-hydroxy-5alpha-androstane 17beta-isobutyrate (8) were synthesized in the present study. Compounds 2 and 8 exhibited higher anabolic activity than the rest of the synthesized compounds. The structure of all these newly synthesized compounds was confirmed by analytic spectral data (mass, (1)H NMR and (13)C NMR).
Reyes-Moreno
M
M
Centro de Química Farmacéutica, Apartado Postal 16042, Ciudad Habana, Cuba.
Ruiz-García
J A
JA
Ibarra-Reyes
Y
Y
Fuente-Hernández
A
A
Vélez-Castro
H
H
Hernández-Balmaseda
I
I
Martínez-Hormaza
I
I
Rodeiro-Guerra
I
I
Ramírez
J Sandoval
JS
Reyes
S Meza
SM
Montiel-Smith
S
S
D045930:Anabolic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000728:Androgens / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000731:Androstanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D005461:Fluorine / Q000737:chemistry / Q000494:pharmacology; D008297:Male; D009132:Muscles / Q000187:drug effects; D009929:Organ Size / Q000187:drug effects; D011467:Prostate / Q000187:drug effects; D051381:Rats; D017208:Rats, Wistar; D012669:Seminal Vesicles / Q000187:drug effects
D045930:Anabolic Agents; D000728:Androgens; D000731:Androstanes; D005461:Fluorine