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Query: UMLS:C0338671 (Steroids)
 9,479 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

3alpha, 7alpha-Dihydroxy-5beta-cholan-24-oic acid in acetic acid was treated with concentrated hydrochloric acid at room temperature. Two of the dehydration products thus obtained proved to correspond to the beta- and gamma-acids reported (5). One (gamma-acid) of these was identified as 3alpha-hydroxy-5beta, 14beta-chol-8-en-24-oic acid (IIa) by means of several spectral measurements of itself and its OsO4 oxidation products. Chemical structure of the other (beta-acid) remains undetermined.
Steroids 1977 Sep
PMID:3alpha-Hydroxy-5beta,14beta-chol-8-en-24-oic acid and its isomer, dehydration products of chenodeoxycholic acid obtained by treatment with concentrated HC1. 59 37

1. Thirty-eight steroids were tested as substrates for a 7 alpha-hydroxy steroid dehydrogenase preparation from a strain of Escherichia coli; an improved method of making the crude enzyme is described. 2. Steroids having a 7 alpha-hydroxyl group in the molecule were substrates except (a) when the 5 beta-cholan-24-oic acid side chain was shortened to less than four carbon atoms and (b) in certain cases when sulphate ester groups were present in the molecule. 3. For testing with the enzyme, a new specimen of 7 alpha-hydroxy-3,12-dioxo-5 beta-cholan-24-oic acid was made, which had properties different from those previously described.
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PMID:The specificity of a 7 alpha-hydroxy steroid dehydrogenase from Escherichia coli. 78 79

Chemical synthesis of 3 alpha,6 beta,7 alpha,12 beta- and 3 alpha,6 beta,7 beta,12 beta-tetrahydroxy-5 beta-cholan-24-oic acids is described. 3 alpha,12 beta-Dihydroxy-5 beta-chol-6-en-24-oic acid used as the starting material in the synthesis was prepared via oxidation of 3 alpha,12 alpha-dihydroxy-5 beta-chol-6-en-24-oic acid 3-hemisuccinate at C-12 followed by reduction with potassium/tertiary amyl alcohol. alpha-Epoxidation of the ester diacetate of 3 alpha,12 beta-dihydroxy-5 beta-chol-6-en-24-oic acid with m-chloroperbenzoic acid followed by cleavage of the epoxide with acetic acid and alkaline hydrolysis yielded 3 alpha,6 beta,7 alpha,12 beta-tetrahydroxy-5 beta-cholan-24-oic acid (overall yield 25%). N-Methylmorpholine-N-oxide-catalyzed osmium tetroxide oxidation of the ester diacetate of 3 alpha,12 beta-dihydroxy-5 beta-chol-6-en-24-oic acid followed by alkaline hydrolysis yielded 3 alpha,6 beta,7 beta,12 beta-tetrahydroxy-5 beta-cholan-24-oic acid (overall yield 33%). The structures of the synthesized bile acids were confirmed from their proto nuclear magnetic resonance and mass spectral fragmentation patterns.
Steroids 1992 Mar
PMID:Synthesis of 3 alpha,6 beta,7 alpha,12 beta- and 3 alpha,6 beta,7 beta,12 beta-tetrahydroxy-5 beta-cholanoic acids. 162 Dec 64

By-products were formed on analysis of beta-muricholic acid (3 alpha, 6 beta, 7 beta-trihydroxy-5 beta-cholan-24-oic acid) in biological samples by a method involving acid-catalyzed solvolysis of sulfate esters in acetone-methanol, followed by perchloric acid-catalyzed acetylation with acetic anhydride-acetic acid. These products have been identified by mass spectrometry and nuclear magnetic resonance as methyl 3-0,6-0-diacetyl-7-0-(1-methyl-3-oxo-1-butenyl)- and methyl 3-0,7-0-diacetyl-6-0-(1-methyl-3-oxo-1-butenyl)-beta-muricholate, methyl 3-0, 6-0-diacetyl- and methyl 3-0, 7-0-diacetyl-beta-muricholate, and a methyl diacetoxy-cholen-24-oate.
Steroids 1989 Jun
PMID:By-products in the analysis of beta-muricholic acid in biological samples as methyl ester triacetate. 281 49

Homoursodeoxycholic acid and [11,12-3H]homoursodeoxycholic acid were synthesized from ursodeoxycholic acid and homocholic acid, respectively. Ursodeoxycholic acid (Ia) was converted to 3 alpha, 7 beta-diformoxy-5 beta-cholan-24-oic acid (Ib) using formic acid. Reaction of the diformoxy derivative (Ib) with thionyl chloride yielded the acid chloride (II) which was treated with diazomethane to produce 3 alpha, 7 beta-diformoxy-25-diazo-25-homo-5 beta-cholan-24-one (III). Homoursodeoxycholic acid (IV) was formed from the diazoketone (III) by means of the Wolff rearrangement of the Arndt-Eistert synthesis. N-Bromosuccinimide oxidation of homocholic acid (V), which was prepared from cholic acid by the same procedure described above, afforded 3 alpha, 12 alpha-dihydroxy-7-oxo-25-homo-5 beta-cholan-25-oic acid (VI). Reduction of the 7-ketohomodeoxycholic acid (VI) with sodium in 1-propanol gave 3 alpha, 7 beta, 12 alpha-trihydroxy-25-homo-5 beta-cholan-25-oic acid (VII). The methyl ester of 7-epihomocholic acid (VII) was partially acetylated to give methyl 3 alpha, 7 beta-diacetoxy-12 alpha-hydroxy-25-homo-5 beta-cholan-25-oate (VIII) using a mixture of acetic anhydride, pyridine and benzene. Dehydration of the diacetoxy derivative (VIII) with phosphorus oxychloride yielded methyl 3 alpha, 7 beta-diacetoxy-25-homo-5 beta-chol-11-en-25-oate (IX). Reduction of the unsaturated ester (IX) with tritium gas in the presence of platinum oxide catalyst followed by alkaline hydrolysis gave [11,12-3H]homoursodeoxycholic acid.
Steroids 1984 Dec
PMID:Synthesis of homoursodeoxycholic acid and [11,12-3H]homoursodeoxycholic acid. 640 Jan 51

7 beta-Methyl-chenodeoxycholic acid (7-MeCDC, 3 alpha, 7 alpha-dihydroxy-7 beta-methyl-5 beta-cholan-24-oic acid), 7 alpha-methyl-ursodeoxycholic acid (7-MeUDC, 3 alpha, 7 beta-dihydroxy-7 alpha-methyl-5 beta-cholan-24-oic acid), 7 xi-methyl-lithocholic acid (7-MeLC, 3 alpha-hydroxy-7 xi-methyl-5 beta-cholan-24-oic acid) and ursodeoxycholylsarcosine (UDCS) were tested as inhibitors of bacterial bile acid 7 alpha-dehydroxylase activity. At a concentration of 50 microM, 7-MeCDC and 7-MeUDC inhibited enzyme activity by 66% and 12%, respectively. 7 alpha-Dehydroxylase activity was not inhibited in the presence of 7-MeLC and UDCS. None of the four bile acid analogs tested inhibited the growth of Eubacterium sp. V.P.I. 12708 at concentrations up to 100 microM.
Steroids 1984 Oct
PMID:Effect of bile acid analogs on 7 alpha-dehydroxylase activity in Eubacterium sp. V.P.I. 12708. 654 70

This article reports the synthesis of the esters of norethisterone (17 alpha-ethynl-17beta-hydroxyestr-4-en-3-one) with 3 bile acids and of the cholesteryl carbonate of norethisterone. The compounds were prepared by reacting the thallium salt of norethisterone with an acid chloride in an organic solvent. Compounds prepared included: t-butyl dimethylsilyl ether of 3alpha-formyloxy-5beta-cholan-24oic acid; 3alpha-formyloxy-5beta-cholan-24-oic acid chloride; norethisterone ester of 3alpha-formyloxy-5beta-cholan-24-oic acid; norethisterone ester of 3alpha-formyloxy-5 beta-cholan-24-oic acid; norethisterone ester of 3alpha, 12alpha-diformyloxy-5beta-cholan-24-oic acid; norethisterone ester of 3 alpha, 7alpha, 12alpha-triformyloxy-5 beta-cholan-24-oic acid; norethisterone ester of 3 beta-acetoxypregn-5-en-20alpha-carboxylic acid; and norethisterone cholesteryl carbonate. This experimentation was part of a program initated by the World Health Organization for the synthesis and screening of new compounds that might be useful as long-acting, injectable contraceptives.
Steroids 1983 Mar
PMID:Long-acting contraceptive agents: bile acid esters of norethisterone. 665 80

In order to find an artificial internal standard compound for quantitative determination of bile acids by gas chromatography, 7 alpha,12 alpha-, 7 alpha, 12 beta-, 7 beta, 12 alpha- and 7 beta,12 beta-dihydroxy-5 beta-cholan-24-oic acids were chemically synthesized with cholic acid (1) as the first starting material. The gas chromatographic retention time of 7 beta,12 beta-dihydroxy-5 beta-cholan-24-oic acid (beta beta-isomer) was more different from that of natural bile acids than the other isomers. Moreover, beta beta-isomer was extracted in the same fraction as the bile acids from urine, and no urinary substance had the same retention time as beta beta-isomer. No artifact was produced from beta beta-isomer during the analysis procedure. It was concluded that the beta beta-isomer is an internal standard compound with certain advantages for the quantitative determination of bile acids in urine by gas chromatography, irrespective of the recovery rate during the analysis procedure.
Steroids 1982 Jun
PMID:7 beta,12 beta-Dihydroxy-5 beta-cholan-24-oic acid as an internal standard for quantitative determination of bile acids by gas chromatography. 715 35

This paper describes three simple and short methods for the conversion of cholic acid into cholylaldehyde with protected hydroxyl groups. The first method involves lithium aluminum hydride reduction of the tetrahydropyranyl ether of methyl cholate and oxidation of the resulting primary alcohol with pyridinium chlorochromate. The second method employs diborane for the reduction of the -COOH group to the -CH2OH group, while the third method involves the reduction of 3 alpha, 7 alpha, 12 alpha-triformyloxy-5 beta-cholan-24-oic acid (as the acid chloride) directly into 3 alpha, 7 alpha, 12 alpha-triformyloxy-5 beta-cholan-24-al with TMA-ferride (tetramethylammonium hydridoirontetracarbonyl). The aldehyde obtained by any of the above methods underwent smooth Reformatsky reaction with ethyl alpha-bromopropionate to yield 3 alpha, 7 alpha, 12 alpha, 24 xi-tetrahydroxy-5 beta-cholestan-26-oic acid.
Steroids 1982 Jun
PMID:Improved synthesis of 3 alpha, 7 alpha, 12 alpha, 24 = xi-tetrahydroxy-5 beta-cholestan-26-oic acid. 715 40

An efficient and convenient procedure for the esterification, deformylation, and deacetylation of bile acids is described. This is achieved by the addition of a catalytic amount of methanesulfonic acid or para-toluene sulfonic acid to a solution of bile acid in methanol in the domestic microwave oven. All these reactions were completed in the microwave oven within 1-3 min at 60% power (390 W) and the desired bile acids, namely trihydroxy-5 beta-cholestanoic acid, (23R)-3 alpha,7 alpha,23-trihydroxy-5 beta-cholan-24-oic acid, ursocholic acid and 7-ketolithocholic acid were isolated in 86-94% yield.
Steroids 1995 Jun
PMID:Microwave-induced organic reactions of bile acids: esterification, deformylation and deacetylation using mild reagents. 767 78


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