Eur J Med Chem. 2009 Nov;44(11):4567-71. Epub 2009 Jul 1.

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

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.

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Centro de Química Farmacéutica, Apartado Postal 16042, Ciudad Habana, Cuba.

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).

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