Azastene
Chemical compound
From Wikipedia, the free encyclopedia
Azastene (INN, USAN) (developmental code name WIN-17625) is a steroidogenesis inhibitor described as a contraceptive, luteolytic, and abortifacient which was never marketed.[1][2] It acts as a competitive inhibitor of 3β-hydroxysteroid dehydrogenase (IC50 = 1 μM), and thereby inhibiting the formation of progesterone, corticosteroids, androgens, and estrogens.[3][4] Due to inhibition of corticosteroid synthesis, azastene is immunosuppressive.[2]
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| Other names | WIN-17625; 4,4,17α-Trimethylandrosta-2,5-dieno(2,3-d)isoxazol-17β-ol |
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| Formula | C23H33NO2 |
| Molar mass | 355.522 g·mol−1 |
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Synthesis
One synthesis of this compound involves initial alkylation of methyl testosterone by means of strong base and methyl iodide to afford the 4,4-dimethyl derivative. Formylation with alkoxide and methyl formate leads to the 2-hydroxymethyl derivative. Reaction of this last with hydroxylamine leads to formation of an isoxazole ring. There is then obtained azastene.
