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

Four possible monoglucuronides of estetrol (estra-1,3,5(10)-triene-3,15 alpha, 16 alpha, 17 beta-tetraol) have been prepared from appropriately protected estetrol by the Koenigs-Knorr reaction employing cadmium carbonate as a catalyst. Condensation of methyl acetobromoglucuronate with estetrol 15,16,17-triacetate provided the 3-glucuronide acetate-methyl ester in a satisfactory yield. Introduction of the glucuronyl residue into C-17 was similarly attained by the use of estetrol 3-benzoate 15,16-acetonide. When estetrol 3,17-diacetate and acetobromosugar were stirred in anhydrous toluene in the presence of cadmium salt, the reaction occurred at C-16 and C-15 yielding two isomeric monoglucuronide derivatives in a ratio of ca. 5 to 2. Removal of the protecting groups in the four glucuronide acetate-methyl esters gave the desired estetrol glucuronides, respectively. These synthetic substrates underwent readily enzymatic hydrolysis with beef-liver beta-glucuronidase to afford estetrol.
Steroids 1976 Jan
PMID:Syntheses of estetrol monoglucuronides. 126 89

3-N-Acetylglucosaminides of unconjugated, glycine- and taurine-conjugated bile acids have been synthesized. Bile acids appropriately protected were condensed with acetochloroglucosamine through the 3 alpha-hydroxyl group by means of the Koenigs-Knorr reaction using cadmium carbonate as a catalyst. Subsequent borohydride reduction and/or alkaline hydrolysis provided desired 3-N-acetylglucosaminides of unconjugated bile acids. Glycine-conjugates were obtained from N-acetylglucosaminides of unconjugated bile acids and ethyl glycinate by the carbodiimide method. The preparation of N-acetylglucosaminides of taurine-conjugates was attained by the Koenigs-Knorr reaction of bile acid p-nitrophenyl esters followed by condensation with taurine. 7-N-Acetylglucosaminides of ursodeoxycholates were prepared in a similar fashion. The convenient synthesis of 3-N-acetylglucosaminides of unconjugated bile acids is also described.
Steroids 1992 Nov
PMID:Synthesis of N-acetylglucosaminides of unconjugated and conjugated bile acids. 144 11

The crystal and molecular structures of the title compounds were determined by x-ray diffractometric analysis. Torsion angles and puckering parameters are reported for both compounds. In 1 the 5 alpha-cyano group influences the A-ring conformation. The carbonate ester 3 crystallizes in the monoclinic P2(1) space group with two molecules (I and II) in the asymmetric unit. The D-ring conformation is to some extent different between I and II.
Steroids 1992 Oct
PMID:X-ray structure analysis of 3,11,17-trioxoandrostane-5 alpha-carbonitrile and of 17 alpha-ethoxycarbonyloxy-3-oxoandrost-4-ene-17-carbonitrile. 145 58

A procedure to detect and quantify nanogram amounts of the contraceptive steroid norethisterone (17alpha-ethinyl-17beta-hydroxy-4-estren-3-one) in human plasma is described. Norgestrel (racemic 13beta-ethyl-17alpha-ethinyl-17beta-hydroxy-4-gonen-3-one) was added to the plasma as an internal reference compound. Norethisterone and norgestrel were isolated from the plasma using a benzene and ammonium carbonate extraction procedure and were treated with trimethylsilylimidazole and potassium acetate to form TMS-enol TMS derivatives. Analyses of norethisterone and norgestrel were done by selective ion detection of the molecular ions using a combination of gas chromatography, mass spectrometry, and a computer.
Steroids Lipids Res 1974
PMID:Analysis of nanogram quantities of norethisterone in plasma using a GC-MS-COM selective ion detection procedure. 442 92

The hydrolysis of 108 esters of norethisterone (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one) was studied in vitro using a rabbit liver preparation. Introduction of a double or triple bond into a straight-chain ester did not inhibit hydrolysis but a marked reduction in hydrolysis was produced on replacement of a methylene group by an oxygen atom. Hydrolysis was inhibited by substituents at C2 of the ester chain except in short chain esters. Cyclopropylcarboxylate and cyclobutylcarboxylate were readily hydrolysed and introduction of a furan ring into the side-chain did not affect hydrolysis. No hydrolysis occurred with a cholesteryl carbonate ester or with a pentamethyldisilyloxy ether. Forty-nine esters of levonorgestrel (13 beta-ethyl-17 alpha-ethynyl-17 beta-hydroxygon-4-en-3-one) were also studied. In general, the pattern of hydrolysis for these esters was similar to that of the norethisterone esters. However, with few exceptions the levonorgestrel esters were hydrolyzed more slowly. For those esters for which information regarding the biological activity was available, there was no correlation between the potency of the esters and their rate of hydrolysis in vitro.
Steroids 1983 Mar
PMID:Long-acting contraceptive agents: in vitro hydrolysis of esters of norethisterone and levonorgestrel. 641 10

Analogs of 7 alpha-hydroxy-4-cholesten-3-one were prepared to ascertain structural features necessary for maximal activity of hepatic microsomal 12 alpha-steroid hydroxylase. Methyl 3 alpha,7 alpha-dihydroxy-5 beta-cholane-24-carboxylate derived from chenodeoxycholic acid was oxidized at C-3 with silver carbonate/Celite. The product was hydrolyzed and dehydrogenated with SeO2 to provide 3-oxo-7 alpha-hydroxy-4-cholene-24-carboxylic acid. 5 beta-Cholestane-3 alpha,7 alpha,25-triol and 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol were similarly oxidized at C-3 and dehydrogenated to provide 7 alpha,25-dihydroxy-4-cholesten-3-one and 7 alpha,12 alpha,25-trihydroxy-4-cholesten-3-one, respectively. The products were characterized by thin-layer and gas chromatography, ultraviolet, infrared, proton resonance and mass spectrometry.
Steroids 1984 Jul
PMID:Bile acids. LXXIII. Synthesis of analogs of 7 alpha-hydroxy-4-cholesten-3-one as substrates for hepatic steroid 12 alpha-hydroxylase. 644 66

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

Controlled alkaline hydrolysis of 16 alpha-bromo-17-keto steroids 1, 5 and 7 with potassium carbonate and tetra-n-butylammonium hydroxide (n-Bu4NOH) and synthesis of 2 alpha-hydroxy-3-ones 11, 13 and 16 by the controlled hydrolysis of the corresponding 2 alpha-bromo-3-ones 9, 12 and 15 are described. Treatment of the bromoketones 1,5 and 7 with potassium carbonate in aqueous acetone or with n-Bu4NOH in aqueous dimethylformamide (DMF) gave 16 alpha-hydroxy-17-ones 3m 6 and 8 in 85-90% yield, respectively. 2 alpha-Hydroxy-3-ones 11, 13 and 16 were obtained by hydrolysis of the corresponding bromoketones 9, 12 and 15 in high yields using the above conditions or sodium hydroxide in pyridine or DMF, respectively. Deuterium labeling experiments suggested that equilibration between the 2 alpha-bromoketone 9 and the 2 beta-bromo isomer 10 precedes the formation of the ketol 11 in which the true intermediate might be the 2 beta-isomer 10. However, rearranged androstane derivatives, 3 beta-hydroxy-2-one 18 and 20, were stereoselectively obtained by treatment of the bromoketones 12 and 15 with an excess amount of sodium hydroxide.
Steroids 1982 Mar
PMID:Controlled alkaline hydrolysis of steroidal alpha-bromoketones: new conditions and synthesis of 2 alpha-hydroxy-3-ones. 709 29

On treatment with methyl 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-alpha-D-glucuronate and silver carbonate, tetrahydrocortisone 21-acetate gave the corresponding 3-glucosiduronate triacetyl methyl ester. This product was converted into the 20-semicarbazone which, by treatment with alkali to hydrolyze the ester functions and acid to hydrolyze the semicarbazone moiety, gave tetrahydrocortisone 3-glucosiduronic acid. The acid was converted into the crystalline barium salt and into the methyl ester. An analogous series of reactions was carried out on tetrahydrocortexolone 21-acetate. Treatment of the 20-semicarbazone of tetrahydrocortisone 3-glucosiduronic acid with potassium borohydride reduced the 11-oxo function to an 11 beta hydroxyl group; acid-catalyzed removal of the semicarbazone group produced tetrahydrocortisol 3-glucosiduronic acid which also was obtained as the barium salt and the methyl ester.
Steroids 1982 Jul
PMID:C-3 glucosiduronates of metabolites of adrenal steroids. 715 44

The synthesis of 15-N-acetylglucosaminides of 15 alpha-hydroxyesterone, 15 alpha-hydroxyestradiol, and 15 alpha-hydroxyestriol (estetrol) is described. The latter two were prepared by condensation of 2-acetamido-1 alpha-chloro-1,2-dideoxy-3,4,6-trio-O-acetyl-D-glucopyranose with appropriately protected 15 alpha-hydroxyestrogens by the Koenigs-Knorr reaction employing cadmium carbonate as a catalyst. Subsequent removal of protecting groups with methanolic potassium hydroxide provided the desired conjugates. 15 alpha-Hydroxyestrone 15-N-acetylglucosaminide was synthesized from the corresponding 15 alpha-hydroxyestradiol derivative by Jones oxidation followed by brief alkaline hydrolysis. These conjugates underwent enzymatic hydrolysis with beta-N-acetylglucosaminidase from Jack beans to produce 15 alpha-hydroxyestrogens.
Steroids 1995 Mar
PMID:Synthesis of 15 alpha-hydroxyestrogen 15-N-acetylglucosaminides. 779 32


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