title: Synthesis of 10 beta-(1'-azirinyl)estr-4-en-3,17-dione as an aromatase inhibitor.
abstract: The novel 10 beta-(1'-azirinyl)estr-4-en-3,17-dione (10) has been synthesized from 19-methyl-19-methiodide salt intermediates 15 and 16 by a modified Neber reaction. Four other hitherto undescribed 10 beta-1'-azirinyl steroids 9, 12, 17, and 18 were also synthesized. Compound 10 inhibited human placental aromatase in vitro (IC50 value = 5.5 microM) but was not as potent as the related (19R)-10 beta-aziridine (1).
authors.affiliation: Pharmazeutische Chemie, Universität des Saarlandes, Saarbrücken, Germany.
authors.forename: V C
authors.initials: VC
authors.lastname: Njar
authors.forename: J
authors.initials: J
authors.lastname: Düerkop
authors.forename: R W
authors.initials: RW
authors.lastname: Hartmann
mesh_terms: D047072:Aromatase Inhibitors; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004963:Estrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy
chemical_list: C099511:10-(1-azirinyl)estr-4-en-3,17-dione; D047072:Aromatase Inhibitors; D004791:Enzyme Inhibitors; D004963:Estrenes