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 17 alpha-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 17 alpha-methyltestosterone. By the same method, after oximation, methylation, and separation, (20R)-20-hydroxypregn-4-en-3-one gave (3E,2OR)-20-hydroxypregn-4-en-3-one 3(O-(2-carboxyethyl)oxime and (3Z,20R)-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.
Pouzar
V
V
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague.
Cerný
I
I
D000179:Acrylates; D019811:Hydroxylamine; D006898:Hydroxylamines; D009682:Magnetic Resonance Spectroscopy; D008777:Methyltestosterone / Q000031:analogs & derivatives*; D015394:Molecular Structure; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry; D011374:Progesterone / Q000031:analogs & derivatives*; D013237:Stereoisomerism; D013739:Testosterone / Q000031:analogs & derivatives*
D000179:Acrylates; D006898:Hydroxylamines; D010091:Oximes; D019811:Hydroxylamine; D013739:Testosterone; D011374:Progesterone; D008777:Methyltestosterone