1173-26-8Relevant articles and documents
Synthesis and characterization of the 6α- and 6β-hydroxylated derivatives of corticosterone, 11-dehydrocorticosterone, and 11-deoxycortisol
Kraan, Gijsbert P. B.,Wee, Kees T. van,Wolthers, Bert G.,Molen, Jan C. van der,Nagel, Gijs T.,et al.
, p. 495 - 503 (1993)
This report describes the synthesis of 6α,17,21- and 6β,17,21-trihydroxypregn-4-ene-3,20-dione, 6α,7,21- and 6β,11β,21-trihydroxypregn-4-ene-3,20-dione, and - for the first time - that of 6α,21- and 6β,21-dihydroxypregn-4-ene-3,11,20-trione. The former four compounds were prepared by 6-hydroxylation of 17,21-dihydroxypregn-4-ene-3,20-dione and 11β,21-dihydroxypregn-4-ene-3,20-dione, respectively. This was achieved by autoxidation or by oxidation with 3-chloroperbenzoic acid, of the 3-methoxypregna-3,5-dienes of the latter two steroids. The yield of the 6β-hydroxylated steroids, but not of their corresponding 6α-epimers, was higher using autoxidation than the peracid. The two 6-hydroxylated pregnenetriones were prepared from 6α,21-diacetoxy-11β-hydroxypregn-4-ene-3,20-dione and 6β,21-diacetoxy-11β-hydroxypregn-4-ene-3,20-dione, respectively, by oxidation with pyridinium chlorochromate. The above-mentioned six steroids were identified and characterized by nuclear magnetic resonance, infrared, ultraviolet, high performance liquid chromatography, gas chromatography, and mass spectrometry. Keywords: synthesis; corticosteroids; 6-hydroxylation; NMR; HPLC; GC/MS.
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v.Euw,Lardon,Reichstein
, p. 1287,1292 (1944)
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NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
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Page/Page column 87; 88, (2014/01/08)
Described herein are neuroactive steroids of the Formula (I) or a pharmaceutically acceptable salt, solvate, stereoisomer, tautomer, and/or isotopic variant thereof; wherein ----, X, Z1, Z2, R1, R2, R3, and R4 are as defined herein, provided at least one of R1, R2, R3, and X a group of the formula -OC(=O)RE1. Such compounds are envisioned, in certain embodiments, to behave as soft drugs and, in certain embodiments, as GABA modulators. The present invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.
Process for preparing 3-enol ethers of 11β-hydroxy-Δ4 -pregnene-3-ones and derivatives thereof
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, (2008/06/13)
3-enol ethers of 11β-hydroxy-Δ4 -pregnene-3-ones are prepared by reacting triethylorthoacetate with an 11β-hydroxy-Δ4 -pregnene-3-one in a solvent which is at least 40% by weight or more ethanol and 60% by weight or less of a compatible oxygenated hydrocarbon liquid in the presence of an acid catalyst. This reaction forms a basis of a process for forming 6-halo-derivatives, particularly 6-chloro-Δ1,4,6 -pregnatrien -11β,17α,21-triol-3,20-dione.
