Synthesis of 10 beta-(1'-azirinyl)estr-4-en-3,17-dione as an aromatase inhibitor.
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).
Njar
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Pharmazeutische Chemie, Universität des Saarlandes, Saarbrücken, Germany.
Düerkop
J
J
Hartmann
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RW
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
C099511:10-(1-azirinyl)estr-4-en-3,17-dione; D047072:Aromatase Inhibitors; D004791:Enzyme Inhibitors; D004963:Estrenes