A concise method for the preparation of deuterium-labeled cortisone: synthesis of [6,7-2H]cortisone.
A method is described for the synthesis of isotopically labeled cortisone from commercially available cortisone acetate through a Delta(4,6)-dieneone. Direct deuteration of the dienone acetate with various catalysts in different solvent systems failed to give an isolable product. Initial hydrolysis of the side-chain ester of the Delta(4,6)-dieneone and subsequent derivatization gave the key intermediate, 17alpha,20;20,21-bismethylenedioxy-pregna-4,6-diene-3,11-dione, which could be satisfactorily deuterated to the desired product. The availability of [6,7-(2)H]cortisone will provide a tool for the future study of the metabolism of cortisone in human tissues.
Sulima
Agnieszka
A
Laboratory of Medicinal Chemistry, Building 8, Room B1-23, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, 8 Center Drive MSC 0815, Bethesda, MD 20892, USA.
Prisinzano
Thomas E
TE
Spande
Thomas
T
Deschamps
Jeffrey R
JR
Whittaker
Noel
N
Hochberg
Zeev
Z
Jacobson
Arthur E
AE
Rice
Kenner C
KC
D003348:Cortisone / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003903:Deuterium; D008401:Gas Chromatography-Mass Spectrometry; D007553:Isotope Labeling / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular
D003903:Deuterium; D003348:Cortisone