title: 3-(Cyclohexenonyl)-4-(4-hydroxyphenyl)-hexanes: antiandrogenes derived from the estrogen hexestrol.
abstract: 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.
authors.affiliation: Sonderforschungsbereich 234, Institut für Pharmazie, Lehrstuhl Pharmazeutische Chemie II, Universität Regensburg.
authors.forename: C D
authors.initials: CD
authors.lastname: Schiller
authors.forename: M R
authors.initials: MR
authors.lastname: Schneider
authors.forename: E
authors.initials: E
authors.lastname: von Angerer
mesh_terms: D000726:Androgen Antagonists / Q000138:chemical synthesis*; D000818:Animals; D005260:Female; D006589:Hexestrol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D008297:Male; D051379:Mice; D009929:Organ Size / Q000187:drug effects; D011817:Rabbits; D013739:Testosterone / Q000097:blood; D014599:Uterus / Q000187:drug effects
chemical_list: D000726:Androgen Antagonists; D006589:Hexestrol; C066434:3-(cyclohex-3-en-1-on-4-yl)-4-(4-hydroxyphenyl)hexane; D013739:Testosterone