4472-02-0Relevant articles and documents
Chemical synthesis of uncommon natural bile acids: The 9α-hydroxy derivatives of chenodeoxycholic and lithocholic acids
Iida, Takashi,Namegawa, Kazunari,Nakane, Naoya,Iida, Kyoko,Hofmann, Alan Frederick,Omura, Kaoru
, p. 1397 - 1402 (2016/10/03)
The chemical synthesis of the 9α-hydroxy derivatives of chenodeoxycholic and lithocholic acids is reported. For initiating the synthesis of the 9α-hydroxy derivative of chenodeoxycholic acid, cholic acid was used; for the synthesis of the 9α-hydroxy derivative of lithocholic acid, deoxycholic acid was used. The principal reactions involved were (1) decarbonylation of conjugated 12-oxo-Δ9(11)-derivatives using in situ generated monochloroalane (AlH2Cl) prepared from LiAlH4 and AlCl3, (2) epoxidation of the deoxygenated Δ9(11)-enes using m-chloroperbenzoic acid catalyzed by 4,4'-thiobis-(6-tert-butyl-3-methylphenol), (3) subsequent Markovnikov 9a-hydroxylation of the Δ9(11)-enes with AlH2Cl, and (4) selective oxidation of the primary hydroxyl group at C-24 in the resulting 3α,9α,24-triol and 3α,7α,9α,24-tetrol to the corresponding C-24 carboxylic acids using sodium chlorite (NaClO2) in the presence of a catalytic amount of 2,2,6,6-tetramethylpiperidine 1-oxyl free radical (TEMPO) and sodium hypochlorite (NaOCl). The 1H- and 13C-NMR spectra are reported. The 3α,7α,9α-trihydroxy-5β-cholan-24-oic acid has been reported to be present in the bile of the Asian bear, and its 7-deoxy derivative is likely to be a bacterial metabolite. These bile acids are now available as authentic reference standards, permitting their identification in vertebrate bile acids.
Synthesis and biological activity of novel deoxycholic acid derivatives
Popadyuk, Irina I.,Markov, Andrey V.,Salomatina, Oksana V.,Logashenko, Evgeniya B.,Shernyukov, Andrey V.,Zenkova, Marina A.,Salakhutdinov, Nariman F.
, p. 5022 - 5034 (2015/08/03)
We report the synthesis and biological activity of new semi-synthetic derivatives of naturally occurring deoxycholic acid (DCA) bearing 2-cyano-3-oxo-1-ene, 3-oxo-1(2)-ene or 3-oxo-4(5)-ene moieties in ring A and 12-oxo or 12-oxo-9(11)-ene moieties in ring C. Bioassays using murine macrophage-like cells and tumour cells show that the presence of the 9(11)-double bond associated with the increased polarity of ring A or with isoxazole ring joined to ring A, improves the ability of the compounds to inhibit cancer cell growth.
synthetic bile acid preparation
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Paragraph 0107, (2015/09/28)
no abstract published
METHODS FOR THE PURIFICATION OF DEOXYCHOLIC ACID
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, (2013/06/05)
Synthetic methods for preparing deoxycholic acid and intermediates thereof, high purity synthetic deoxycholic acid, compositions and methods of use are provided. Also, provided are processes for the synthesis of 12-keto or 12-α-hydroxy-steroids from Δ-9,11-ene, 11-keto or 11-hydroxy-β-steroids. This invention is also directed to novel compounds prepared during the synthesis. This invention is also directed to the synthesis of deoxycholic acid starting from hydrocortisone.
SYNTHETIC BILE ACID COMPOSITIONS AND METHODS
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Paragraph 0125, (2013/10/07)
Bile acids and related compositions and methods of synthesis and use. More specifically, deoxycholic acid and related compositions, said compositions being free of all moieties of animal origin and free of pyrogenic moieties.
SYNTHETIC BILE ACID COMPOSITIONS AND METHODS
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Page/Page column 47, (2012/03/09)
Bile acids and related compositions and methods of synthesis and use. More specifically, deoxycholic acid and related compositions, said compositions being free of all moieties of animal origin and free of pyrogenic moieties.
METHODS FOR THE PURIFICATION OF DEOXYCHOLIC ACID
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, (2011/07/07)
Synthetic methods for preparing deoxycholic acid and intermediates thereof, high purity synthetic deoxycholic acid, compositions and methods of use are provided. Also, provided are processes for the synthesis of 12-keto or 12-α-hydroxysteroids from Δ-9,11-ene, 11-keto or 11-hydroxy-β-steroids. This invention is also directed to novel compounds prepared during the synthesis. This invention is also directed to the synthesis of deoxycholic acid starting from hydrocortisone.
A Practical Catalytic Method for the Preparation of Steroidal 1,4-Dien-3-ones by Oxygen Atom Transfer from Iodoxybenzene to Diphenyl Diselenide
Barton, Derek H. R.,Godfrey, Christopher R. A.,Morzycki, Jacek W.,Motherwell, William B.,Ley, Steven V.
, p. 1947 - 1952 (2007/10/02)
The dehydrogenation of steroidal 3-ketones can be accomplished in high yield using benzeneseleninic anhydride generated in situ by efficient oxygen atom transfer from iodoxybenzene to catalytic amounts of diphenyl diselenide.An experimentally convenient and economical development of this catalytic cycle is the use of meta-iodoxybenzoic acid which both avoids chromatography and allows recovery of meta-iodobenzoic acid and diphenyl diselenide. 12-Hydroxy- and 12-keto-steroids are also dehydrogenerated very efficiently using this catalytic process.
