Topterone

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Topterone
Topterone.svg
Identifiers
CAS number 60607-35-4
PubChem 9797605
Jmol-3D images Image 1
Properties
Molecular formula C22H34O2
Molar mass 330.50 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

Topterone, WIN 17,665 (17 alpha-propyltestosterone) is an antiandrogen.[1]

Synthesis[edit]

Reaction of the tetrahydropyranyl ether of dehydroepiandrosterone with propyl magnesium bromide gives after removal of the protecting group the corresponding 17α-propyl derivative. Oppenauer oxidation leads to the corresponding conjugated ketone. There is thus obtained topterone.[2]

References[edit]

  1. ^ Ferrari, RA; Chakrabarty, K; Creange, JE; Beyler, AL; Potts, OG; Schane, HP (1980). "Endocrine profile of topterone, a topical antiandrogen, in three species of laboratory animals". Methods and findings in experimental and clinical pharmacology 2 (2): 65–9. PMID 7339330. 
  2. ^ A. L. Beyler and R. A. Ferrari, DE 2633925  (1977).