SYNTHESIS OF 20-HYDROXY-17,21-CYCLOPREGNANE DERIVATIVES - POTENTIAL C-20 OXO STEROID OXIDOREDUCTASE INHIBITORS

Authors
ORR JC TEMPLETON JF MAJGIERBARANOWSKA H MARAT K
Citation
Jc. Orr et al., SYNTHESIS OF 20-HYDROXY-17,21-CYCLOPREGNANE DERIVATIVES - POTENTIAL C-20 OXO STEROID OXIDOREDUCTASE INHIBITORS, Journal of the Chemical Society. Perkin transactions. I, (18), 1994, pp. 2667-2670
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
18
Year of publication
1994
Pages
2667 - 2670
Database
ISI
SICI code
0300-922X(1994):18<2667:SO2D-P>2.0.ZU;2-U
Abstract
20 alpha- and 20 beta-Hydroxy-17 alpha,21 alpha-cyclopregnane derivati ves, potential mechanism-based-inhibitors fo 20 alpha-, and 2-beta-ste roid oxidoreductases, have been synthesized by conversion of the stero id 17 beta-aldehyde into the 20-tert-butyldimethylsilyl enol ether fol lowed by addition of methylene prepared from the Simmons-Smith reagent . Enzyme inhibition studies show that neither 20 alpha- nor 20 beta-hy droxy-17 alpha,21 alpha-cyclopregn-4-en-3-one were inhibitors of the r espective enzymes from streptomyces hydrogenans.