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.
NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
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, (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.
Determination of saikosaponin derivatives in Radix bupleuri and in pharmaceuticals of the Chinese multiherb remedy Xiaochaihu-tang using liquid chromatographic tandem mass spectrometry
Bao, Yuanwu,Li, Chuan,Shen, Heongwu,Nan, Fajun
, p. 4208 - 4216 (2007/10/03)
Saikosaponins are bioactive oleanane saponins derived from the Chinese medicinal herb Radix bupleuri ("chaihu" in Chinese). An LC-MS/MS-hased method has been developed for characterization and quantification of 15 saikosaponin derivatives (saikosaponin a, saikosaponin b1, saikosaponin g, saikogenin A, saikogenin H, saikosaponin C2, saikosaponin B2, saikosaponin i, prosaikogenin C2, prosaikogenin B2, saikogenin C, saikogenin B, saikosaponin d, saikosaponin b2, and saikogenin D) in one chromatographic run. Optimization of the ionization process was performed with electrospray and atmospheric pressure chemical ionization techniques in both positive and negative ion modes. Negative ion ESI was adopted for generation of the precursor deprotonated molecules to achieve the best ionization sensitivity for the analytes. In addition, the most abundant fragment ion was chosen for each analyte to give the best CID sensitivity. Because some of the saponin derivatives are isomeric, complete resolution for the whole analytes was achieved both chromatographically and mass spectroscopically. Furthermore, optimal internal standard was successfully discovered for determination of the analytes by making use of a combinatorial chemistry approach. Good linearity over the range ～1.65 or 4.98 to 1200 ng/mL for the analytes was observed. The intraday accuracy and precision at nominal low, intermediate, and high concentration varied between 0.8 and 11.8% and between 80 and 116%, respectively, whereas those for interday assay were between 1.1 and 15.5% and between 86 and 119%, respectively. The lower limits of quantitation for the test compounds were ～16.5 to 49.4 pg on-column. The new method offered higher sensitivity and greater specificity than previously reported LC methods. After the validation, the applicability of the method for determination of these chemicals present in a variety of crude chaihu roots and in different brands of the Chinese multiherb remedy Xiaochaihu-tang (or Shosaiko-to) extract granules has been demonstrated. The sensitivity and specificity of the technique will be the basis of a method for the accurate quantification of the saikosaponin derivatives in biomatrixes.
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.
