Lipase-catalyzed preparation of corticosteroid 17α-esters endowed with antiandrogenic activity

Tetrahedron Letters

Volumn 49, Issue 31, 2008, Pages 4610-4612

  Ferraboschi, Patrizia ^a   Mieri, Maria De ^a   Ragonesi, Laura ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b COSMO Pharmaceutical SpA ^*  (Italy)

Author keywords

Antiandrogen; Chemoselective alcoholysis; Corticosteroid; Lipase

Indexed keywords

CORTEXOLONE 17ALPHA PROPIONATE; CORTICOSTEROID; CORTODOXONE; DELTA9 CORTEXOLONE 17ALPHA BUTYRATE; TRIACYLGLYCEROL LIPASE;

ALCOHOLYSIS; ARTICLE; DRUG ACTIVITY; DRUG SYNTHESIS; ENZYME MECHANISM; HYDROLYSIS;

EID: 45049087020     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.086     Document Type: Article

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12. 3).
13. 3).
14. 3).
15. 3).
16. 3).
17. 9-derivative was prepared according a reported procedure starting from cortisol:. Chamberlin E.M., Tristram E.W., Utne T., and Chemerda J.M. J. Org. Chem. 25 (1960) 295
18. 3/AcOEt) until starting material disappearance (24 h). The enzyme was removed by filtration on a Celite pad. After evaporation of solvent at reduced pressure pure cortexolone, 17α-propionate 3b was recovered (0.420 g, 96%). Crystallization from isopropylether afforded 3b with the required purity for biological test (>99% by HPLC).
19. 3-18). Mp 133 °C (t-butylmethylether).
20. 3-18). Mp 195 °C (acetone/diethylether).
21. 3-18). Mp 135 °C (isopropylether).
22. 3-18). Mp 114 °C (isopropylether).
23. 3-18). Mp 136 °C (acetone/hexane).