Preparation and properties of 3-( O-(2-carboxyethyl))oxime derivatives of steroid hormones

Mixtures of 3E and 3Z isomers of 3-( O-(2-carboxyethyl))oxime (CEO) derivatives of testosterone and 17α-methyltestosterone were prepared by reaction with ( O-(2-carboxyethyl))hydroxylamine. These isomers were separated after conversion into methyl esters, and mild alkaline hydrolysis recovered pure...

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Bibliographic Details
Published in:Steroids 1996-02, Vol.61 (2), p.89-93
Main Authors: Pouzar, Vladimír, Černý, Ivan
Format: Article
Language:English
Subjects:
Acrylates
Hydroxylamine
Hydroxylamines
Magnetic Resonance Spectroscopy
Methyltestosterone - analogs & derivatives
Molecular Structure
Oximes - chemical synthesis
Oximes - chemistry
Progesterone - analogs & derivatives
proton NMR spectra
separation of isomers
Stereoisomerism
steroid 3-( O-(2-carboxyethyl))oxime
synthesis
Testosterone - analogs & derivatives
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Summary:Mixtures of 3E and 3Z isomers of 3-( O-(2-carboxyethyl))oxime (CEO) derivatives of testosterone and 17α-methyltestosterone were prepared by reaction with ( O-(2-carboxyethyl))hydroxylamine. These isomers were separated after conversion into methyl esters, and mild alkaline hydrolysis recovered pure E Z - isomers of 3-CEO derivatives of testosterone and 17α-methyltestosterone. By the same method, after oximation, methylation, and separation, (20 R)-20-hydroxypregn-4-en-3-one gave (3 E,20 R)-20-hydroxypregn-4-en-3-one 3( O-(2-carboxyethyl))oxime and (3 Z,20 R)-20-hydroxypregn-4-en-3-one 3-( O-(2-carboxyethyl))oxime methyl esters. The oxidation and subsequent hydrolysis of these compounds produced 3E and 3Z isomers of the 3-CEO derivative of progesterone. Pure E Z - isomers of 3-CEO derivatives are designed for the development of immunoanalytical systems, which make use of the bridge heterology based on the geometric isomerism.
ISSN:0039-128X
1878-5867
DOI:10.1016/0039-128X(95)00198-Y