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3‐(Cyclohexenonyl)‐4‐(4‐hydroxyphenyl)‐hexanes: Antiandrogenes Derived from the Estrogen Hexestrol
Author(s) -
Schiller ClausD.,
Schneider Martin R.,
Angerer Erwin Von
Publication year - 1990
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19903230708
Subject(s) - hexestrol , chemistry , estrogen , diethylstilbestrol , biochemistry , biology , endocrinology , hormone
Selective Birch ‐reduction of one of the phenolic rings of meso ‐ or d , l ‐HES led to compounds 6a and 6b which exert a higher binding affinity to the androgen receptor as the respective parent HES. In vivo testing of 6a and 6b shows that 6a has the same potency in reducing accessory sex organ weights and testosterone levels in the intact mouse as has meso ‐HES, but strongly decreased estrogenic activity. Syntheses and testing of 7 having no ethyl side chains revealed the necessity of these groups for biological activity.