Syntheses of 19-[O-(carboxymethyl)oxime] haptens of epipregnanolone and pregnanolone

Steroids

Volumn 71, Issue 2, 2006, Pages 120-128

  Černý, Ivan ^a   Pouzar, Vladimír ^a   Hill, Martin ^b   Havlíková, Helena ^b   Hampl, Richard ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b INSTITUTE OF ENDOCRINOLOGY   (Czech Republic)

Author keywords

O (Carboxymethyl)oxime; Pregnanolone; Synthesis

Indexed keywords

3BETA HYDROXY 5BETA PREGNAN 20 ONE; 5BETA PREGNANOLONE DERIVATIVE; ELTANOLONE; HAPTEN; UNCLASSIFIED DRUG;

ARTICLE; DEACETYLATION; ESTERIFICATION; OXIDATION; SYNTHESIS;

HAPTENS; MOLECULAR CONFORMATION; OXIMES; PREGNANOLONE; STEREOISOMERISM;

EID: 30644464551     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2005.09.002     Document Type: Article

References (25)

1. A.D. Barbosa, and G.S. Morato Effect of epipregnanolone and pregnenolone sulfate on chronic tolerance to ethanol Pharmacol Biochem Behav 67 2000 459 464
2. I.M. Johansson, V. Birzniece, C. Lindblad, T. Olsson, and T. Backstrom Allopregnanolone inhibits learning in the Morris water maze Brain Res 934 2002 125 131
3. F. van Broekhoven, and R.J. Verkes Neurosteroids in depression: a review Psychopharmacology 165 2003 97 110
4. J. Klak, M. Hill, A. Pařízek, H. Havlíková, M. Bičíková, and R. Hampl Pregnanolone isomers, pregnenolone and their polar conjugates around parturition Physiol Res 52 2003 211 221
5. B.E.P. Murphy, F.V. Abbott, C.M. Allison, C. Watts, and A.M. Ghadirian Elevated levels of some neuroactive progesterone metabolites, particularly isopregnanolone, in women with chronic fatigue syndrome Psychoneuroendocrinology 29 2004 245 268
6. D. Belelli, and K.W. Gee 5α-Pregnan-3α,20α-diol behaves like a partial agonist in the modulation of GABA-stimulated chloride ion uptake by synaptoneurosomes Eur J Pharmacol 167 1989 173 176
7. A receptors Neuropharmacology 32 1993 59 63
8. A receptor Eur J Pharmacol 269 1994 157 163
9. ++ responses: structure-activity studies J Pharmacol Exp Ther 271 1994 677 682
10. A receptor antagonists J Neurosci 22 2002 3366 3375
11. K.D.W. Morris, and J. Amin Insight into the mechanism of action of neuroactive steroids Mol Pharmacol 66 2004 56 69
12. P. Carl, S. Hogskilde, T. Lang-Jensen, V. Bach, J. Jacobsen, and M.B. Sorensen Pharmacokinetics and pharmacodynamics of eltanolone (pregnanolone), a new steroid intravenous anaesthetic, in humans Acta Anaesthesiol Scand 38 1994 734 741
13. A. Pařízek, M. Hill, R. Kancheva, H. Havlí ková, L. Kancheva, and J. Cindr Neuroactive pregnanolone isomers during pregnancy J Clin Endocrinol Metab 90 2005 395 403
14. M. Hill, A. Pařízek, M. Bičíková, H. Havlíková, J. Klak, and T. Fajt Neuroactive steroids, their precursors, and polar conjugates during parturition and postpartum in maternal and umbilical blood. Part 1: identification and simultaneous determination of pregnanolone isomers J Steroid Biochem Mol Biol 75 2000 237 244
15. B.E.P. Murphy, and C.M. Allison Determination of progesterone and some of its neuroactive ring A-reduced metabolites in human serum J Steroid Biochem Mol Biol 74 2000 137 142
16. S.Y. Liu, J. Sjovall, and W.J. Griffiths Neurosteroids in rat brain: extraction, isolation, and analysis by nanoscale liquid chromatography- electrospray mass spectrometry Anal Chem 75 2003 5835 5846
17. B. Cook, and G.H. Beastall Measurement of steroid hormone concentration in blood, urine and tissues B. Green R.E. Leake Steroid hormones: a practical approach 1987 IRL Press Oxford and Washington, DC 13 15
18. O. Lapčík, R. Hampl, M. Hill, M. Bičí ková, and L. Stárka Immunoassay of 7-hydroxysteroids. Part 1: radioimmunoassay of 7β-hydroxy dehydroepiandrosterone J Steroid Biochem Mol Biol 67 1998 439 445
19. O. Lapčík, R. Hampl, M. Hill, and L. Stárka Immunoassay of 7-hydroxysteroids. Part 2: radioimmunoassay of 7α-hydroxy-dehydroepiandrosterone J Steroid Biochem Mol Biol 71 1999 231 237
20. A. Bowers, R. Villotti, J.A. Edwards, E. Desot, and O. Halpern Steroids CCII: a new route to 19-nor steroids J Am Chem Soc 84 1962 3204 3205
21. J. Kalvoda, K. Heusler, H. Ueberwasser, G. Anner, and A. Wettstein 19-Norsteroide IV: about the reductive cleavage of 5α-halogeno-6β,19- oxido-steroids (Über die reduktive Ätherspaltung bei 5α-Halogen-6β,19-oxido-steroiden) Helv Chim Acta 46 1963 1361 1369
22. D. Hauser, K. Heusler, J. Kalvoda, K. Schaffner, and O. Jeger Fragmentation and intramolecular abstraction of tertiary hydrogen atom induced by primary oxyradicals with fixed reaction centers (Fragmentieren und intramolekulare Abstraktionen tertiärer Wasserstoffatome ausgehend von primären Oxyradikalen mit fixierten Reaktionzentren) Helv Chim Acta 47 1964 1961 1979
23. G. Bach, J. Capitaine, and C.R. Engel Steroids and related products. XXV. Cardiotonic steroids. Part II: the synthesis of 17β-substituted 14(15)-unsaturated steroids of the A/B-cis series. Part I Can J Chem 46 1968 733 749
24. I. Černý, H. Havlíková, M. Hill, R. Hampl, and V. Pouzar Synthetic approach to 5α-pregnanolone 19-[O-(carboxymethyl) oxime] derivatives Collect Czech Chem Commun 69 2004 1805 1817
25. M. Joselevich, A.A. Ghini, and G. Burton 6,19-Carbon-bridged steroids: synthesis of 6,19-methanoprogesterone Org Biomol Chem 1 2003 939 943