Azastene

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Azastene
Azastene.svg
Identifiers
CAS number 13074-00-5
PubChem 11725766
ChemSpider 9900482
ChEMBL CHEMBL2103987
Jmol-3D images Image 1
Properties
Molecular formula C23H33NO2
Molar mass 355.51 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Azastene is a chemical that modulates 3β-hydroxysteroid dehydrogenase activity.[1]

Synthesis[edit]

Azastene synthesis:[2]

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.

References[edit]

  1. ^ Liu, CG; Dai, MZ; Li, WK; Liu, GM; Lin, ZM; Ma, RH (1987). "Interceptive action of azastene and its effects on plasma progesterone in pregnant rats and rabbits". Zhongguo yao li xue bao = Acta pharmacologica Sinica 8 (6): 540–3. PMID 3451668. 
  2. ^ Gordon O. Potts, Sterling Drug Inc. U.S. Patent 3,966,926 (1976).