Synthesis and anabolic/androgenic evaluation of novel 9alpha-fluorosteroids.

Authors :: Reyes-Moreno M
Ruiz-García JA
Ibarra-Reyes Y
Fuente-Hernández A
Vélez-Castro H
Hernández-Balmaseda I
Martínez-Hormaza I
Rodeiro-Guerra I
Ramírez JS
Reyes SM
Montiel-Smith S
Source :: European journal of medicinal chemistry [Eur J Med Chem] 2009 Nov; Vol. 44 (11), pp. 4567-71. Date of Electronic Publication: 2009 Jul 01.
Publication Year :: 2009
Abstract: 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).