Addition of Azoimide to Unsaturated Ketones in the Steroid Series. Synthesis of N-(17β-Hydroxy-3-oxo-5α-androstan-15β-yl)succinamoic Acid and Its Evaluation as Hapten for Dihydrotestosterone Immunoanalysis

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Title:Addition of Azoimide to Unsaturated Ketones in the Steroid Series. Synthesis of N-(17β-Hydroxy-3-oxo-5α-androstan-15β-yl)succinamoic Acid and Its Evaluation as Hapten for Dihydrotestosterone Immunoanalysis
Creators:
Černý, Ivan
Pouzar, Vladimír
Lapčík, Oldřich
Hampl, Richard
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 12, pp. 1931-1939
Uncontrolled Keywords:DHT, Haptens, Steroids, Azoimide

Abstract

Addition of azoimide to 17-oxoandrosta-5,15-dien-3β-yl acetate or 17-oxo-5α-androst-15-en-3β-yl acetate gave in both cases corresponding 15β-azido derivatives. 15β-Azido-17-oxo-5α-androstan-3β-yl acetate was selectively reduced to 17β-hydroxy derivative and protected as methoxymethyl ether. Subsequent reduction of azide group and condensation with methyl hydrogen succinate gave a protected succinylamino derivative. Deacetylation and oxidation then led to dihydrotestosterone (DHT) series. Successive removal of protecting groups gave <i>N</i>-(17β-hydroxy-3-oxo-5α-androstan-15β-yl)succinamoic acid, an experimental hapten for DHT. Its conjugate with bovine serum albumin was used for immunization of rabbits and corresponding antisera were evaluated in RIA using [<sup>3</sup>H]-DHT as a tracer. The results are comparable with standard kits based on antisera generated using DHT derivatives with connecting bridge in position 7.

Title:Addition of Azoimide to Unsaturated Ketones in the Steroid Series. Synthesis of N-(17β-Hydroxy-3-oxo-5α-androstan-15β-yl)succinamoic Acid and Its Evaluation as Hapten for Dihydrotestosterone Immunoanalysis
Creators:
Černý, Ivan
Pouzar, Vladimír
Lapčík, Oldřich
Hampl, Richard
Uncontrolled Keywords:DHT, Haptens, Steroids, Azoimide
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:62
Number:12
Page Range:pp. 1931-1939
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19971931UNSPECIFIED
ID Code:1266
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Černý, Ivan; Pouzar, Vladimír; Lapčík, Oldřich; Hampl, Richard (1997) Addition of Azoimide to Unsaturated Ketones in the Steroid Series. Synthesis of N-(17β-Hydroxy-3-oxo-5α-androstan-15β-yl)succinamoic Acid and Its Evaluation as Hapten for Dihydrotestosterone Immunoanalysis. Collection of Czechoslovak Chemical Communications, 62 (12). pp. 1931-1939. ISSN 0010-0765

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