Synthesis of two new haptens of 16alpha-hydroxydehydroepiandrosterone (3beta,16alpha-dihydroxyandrost-5-en-17-one).
Synthetic routes leading to 19E and 7Z O-(carboxymethyl)oximes derived from 16alpha-hydroxydehydroepiandrosterone were developed using two independent methods for introduction of the 16alpha-hydroxy group. Firstly, the oxime moiety was built, and then, either epoxidation of the enol acetate followed by the boron trifluoride mediated rearrangement or alkaline hydrolysis of the corresponding alpha-bromide in aqueous N,N-dimethylformamide were employed. The last step in both methods was removal of the protecting groups, which consisted of acid deprotection of the acetates and gentle alkaline hydrolysis of the methyl ester. Final haptens were designed as components for immunoanalytical kits.
Pouzar
Vladimír
V
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic. pouzar@uochb.cas.cz
Cerný
Ivan
I
Lapcík
Oldrich
O
Hill
Martin
M
Hampl
Richard
R
D003687:Dehydroepiandrosterone / Q000031:analogs & derivatives / Q000737:chemistry*; D006241:Haptens / Q000737:chemistry*; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D006241:Haptens; C011277:16-hydroxydehydroepiandrosterone; D003687:Dehydroepiandrosterone