Synthesis of multi-labeled cortisols and cortisones with (2)H and (13)C for study of cortisol metabolism in humans.
A method is described for the preparation of multi-labeled cortisol and cortisone with (13)C and (2)H via the indan synthon method, starting from chiral 11-oxoindanylpropionic acid. [1, 3-(13)C(2)]Acetone was used for the syntheses of [1,2,4, 19-(13)C(4)]cortisol (cortisol-(13)C(4)) and [1,2,4, 19-(13)C(4)]cortisone (cortisone-(13)C(4)), and [1,3-(13)C(2),1,1,1, 3,3,3-(2)H(6)]acetone was for [1,2,4,19-(13)C(4),1,1,19,19, 19-(2)H(5)]cortisol (cortisol-(13)C(4),(2)H(5)) and [1,2,4, 19-(13)C(4),1,1,19,19,19-(2)H(5)]cortisone (cortisone-(13)C(4), (2)H(5)). The chemical shifts for the (13)C and (1)H NMR spectra of cortisol and cortisone were fully assigned.
Furuta
T
T
Department of Medicinal Chemistry, School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo, Japan.
Eguchi
N
N
Yokokawa
A
A
Shibasaki
H
H
Kasuya
Y
Y
D002247:Carbon Isotopes; D003348:Cortisone / Q000138:chemical synthesis*; D003903:Deuterium; D008401:Gas Chromatography-Mass Spectrometry / Q000592:standards; D006854:Hydrocortisone / Q000138:chemical synthesis* / Q000378:metabolism; D007553:Isotope Labeling / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy
D002247:Carbon Isotopes; D003903:Deuterium; D003348:Cortisone; D006854:Hydrocortisone