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Starting from 3-acetoxy-15-cyano-17-oxo-16,17-seco-5-androstene (2) and 3-ace- toxy-15-cyano-17-hydroxy-17-methyl-16,17-seco-5-androstene (11), new 17-halo-derivatives (5-10 and13) were obtained. The fluoro derivative5 was obtained from 17-tosylate4 in reaction with tetrabutylammonium fluoride. The structure of the 17-iodo-devitive10 was unambiguously proved by the appropriate X-ray structural analysis. Compounds5-10, as well as12 and13, were tested for possible anti-aromatase activity, whereby only compound 9, with bromine as the C-17 substituent, induced 19.4 % inhibition of aromatase activity compared to the control.

Synthesis, crystal structure and antiaromatase activity of 17-halo-16,17-seco-5-androstene derivatives