Abstract
The oxime formation reaction of therapeutical progestogen (levonorgestrel, levonorgestrel acetate, norethisterone), androgen (methyltestosterone, testosterone phenylpropionate) and anabolic (nortestosterone phenylpropionate) Delta 4-3-ketosteroids has been investigated. The ketosteroid-hydroxylamine reaction was monitored by reversed phase HPLC system. It was established, that under the experimental conditions applied the oxime formation was complete within 2 h. The reaction leads to the formation of Z and E oxime isomers. The isomers of norgestimate (levonorgestrel 17-acetate oxime) and other Delta 4-3-ketosteroid oximes have been separated by a new normal phase HPLC method. The identification (elution order assignation) and determination of the formation ratio of the isomers have been performed by 1H NMR spectroscopy on the basis of the chemical shift differences of 4-H signals. The on-line CD and UV spectra of the pure oxime isomers were recorded and then molar ellipticities and absorbances of the isomers were calculated in the wavelength range of 200-300 nm via parameter estimation method.
Keywords: circular dichroism, norgestimate, ketosteroid oxime, levonorgestrel, levonorgestrel acetate norethisterone, methylestosterone, testosterone phenylpropionate, ketsteroids
Current Medicinal Chemistry
Title: Determination of Circular Dichroism and Ultraviolet Spectral Parameters of Norgestimate- and Other Delta4-3-Ketosteroid Oxime Isomers Via Normal Phase HPLC Method
Volume: 8 Issue: 11
Author(s): A. Szentesi, A. Gergely, P. Horvath, S. Maho, P. Matyus and Gy. Szasz
Affiliation:
Keywords: circular dichroism, norgestimate, ketosteroid oxime, levonorgestrel, levonorgestrel acetate norethisterone, methylestosterone, testosterone phenylpropionate, ketsteroids
Abstract: The oxime formation reaction of therapeutical progestogen (levonorgestrel, levonorgestrel acetate, norethisterone), androgen (methyltestosterone, testosterone phenylpropionate) and anabolic (nortestosterone phenylpropionate) Delta 4-3-ketosteroids has been investigated. The ketosteroid-hydroxylamine reaction was monitored by reversed phase HPLC system. It was established, that under the experimental conditions applied the oxime formation was complete within 2 h. The reaction leads to the formation of Z and E oxime isomers. The isomers of norgestimate (levonorgestrel 17-acetate oxime) and other Delta 4-3-ketosteroid oximes have been separated by a new normal phase HPLC method. The identification (elution order assignation) and determination of the formation ratio of the isomers have been performed by 1H NMR spectroscopy on the basis of the chemical shift differences of 4-H signals. The on-line CD and UV spectra of the pure oxime isomers were recorded and then molar ellipticities and absorbances of the isomers were calculated in the wavelength range of 200-300 nm via parameter estimation method.
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Cite this article as:
Szentesi A., Gergely A., Horvath P., Maho S., Matyus P. and Szasz Gy., Determination of Circular Dichroism and Ultraviolet Spectral Parameters of Norgestimate- and Other Delta4-3-Ketosteroid Oxime Isomers Via Normal Phase HPLC Method, Current Medicinal Chemistry 2001; 8 (11) . https://dx.doi.org/10.2174/0929867013372238
DOI https://dx.doi.org/10.2174/0929867013372238 |
Print ISSN 0929-8673 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-533X |
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