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

Reaction of estradiol-17 beta with triethylamine-sulfur trioxide in pyridine gives exclusively monosulfation at the C17-hydroxyl group with the preparation of 17 beta-sulfooxyestra-1,3,5(10)-trien-3-ol triethylammonium salt (V). The structural assignment suggested by spectroscopic measurements was confirmed by synthetic studies. (Formula: see text) A synthesis of 3-sulfooxyestra-1,3,5(10)-trien-17 beta-ol triethylammonium salt (II) has been accomplished based on the preparation of 17 beta-formyloxyestra-1,3,5(10)-trien-3-ol (XIII). Fusion of the 3-sulfate triethylammonium salt II gives rise to the 17-sulfate triethylamine salt V. The preparation of estradiol-17 beta disulfate has also been achieved.
Steroids
PMID:The preparation of estradiol-17 beta sulfates with triethylamine-sulfur trioxide. 383 54

Synthetic vitamin D3 sulfate was prepared by reacting cholecalciferol with sulfamic acid in pyridine. Vitamin D3 sulfate ammonium salt was purified by crystallisation and transformed in sulfate sodium salt. Homogeneity was controlled by reverse phase high pressure liquid chromatography (HPLC). Purified synthetic vitamin D3 sulfate sodium salt was used as a reference. Milk whey was obtained after protein precipitation by adding ethanol. Vitamin D3 sulfoconjugate was identified in supernatant (lyophylized) after purification by Sephadex LH 20 and HPLC. Milk whey purified fraction obtained exhibited the same ultra-violet absorption (UV) as synthetic vitamin D3 sulfate; after solvolysis, cholecalciferol was liberated from natural and synthetic sulfoconjugate. The results confirmed that vitamin D3 sulfate was present in human milk.
Steroids 1982 Apr
PMID:Cholecalciferol sulfate identification in human milk by HPLC. 629 30

Fast atom bombardment (FAB) mass spectra of 13 intact, underivatized glucuronides and/or sulfate salts are reported. Spectra are characterized by abundant ions formed by attachment of a proton, [M+H]+, or of an alkali ion, [M+alkali]+, to the glucuronide or sulfate salt. Fragment ions were of low intensity. FAB spectra can be used to obtain the molecular weight of a sample, to assess its purity and to identify the nature of the alkali of the glucuronide or sulfate salt.
Steroids 1982 Jun
PMID:Fast atom bombardment mass spectrometry of estrogen glucuronides and sulfates. 629 26

This paper describes the synthesis of esters of levonorgestrel (13 beta-ethyl-17 beta-ethynyl-17 beta-hydroxygon-4-en-3-one) with a variety of unsaturated carboxylic acids for evaluation as potential longacting injectable contraceptive agents. 1-Cyclohexenylacetic acid was prepared by the hydrolysis of 1-cyclohexenylacetonitrile. The synthesis of E-penta-2,4-dienoic acid was achieved by the condensation of acrolein with malonic acid. Reformatsky reaction between crotonaldehyde and ethyl 2-bromopropionate followed by dehydration of the condensation product was used for the synthesis of E,E-2-methylhexa-2,4-dienoic acid. In the preparation of 5-methyl-2-furylacetic acid, 5-methylfurfural was subjected to condensation reaction with rhodanine followed by hydrolysis. The levonorgestrel esters were synthesized by reaction of the appropriate acid chloride with the thallim salt of levonorgestrel, which was obtained by use of thallous ethoxide. The esters prepared were levonorgestrel 1-cyclohexenylacetate; levonorgestrel 1-cyclopentenylacetate; levonorgestrel E-penta-2,4-dienoate; levonorgestrel E,E-2methylhexa-2,4-dienoate; levonorgestrel 5-methyl-2-furylethaoate; levonorgestrel 3-(5'-methyl-2'-furyl)propanoate; levonorgestrel 3-(5'-ethyl-2'-furyl)propanoate; leveonorgestrel 4-(5'-methyl-2'-furyl)butanoate; levonorgestrel E-non-2-en-4-ynoate; 1-cyclohexenylacetic acid; 1-cyclopentenylacetic acid; E-penta-2,4-dienoic acid; E,E-2-methylhexa-2,4-dienoic acid; 5-methyl-2-furylacetic acid; and E-non-2-en-4-ynoic acid.
Steroids 1983 Mar
PMID:Long-acting contraceptive agents: levonorgestrel esters of unsaturated acids. 641 7

Nuclear binding of corticosteroids in fish tissues was investigated in two target organs of the trout Salmo gairdnerii irideus: the liver and the intestinal mucosa. Incubation of intact nuclei with [3H]-cortisol or [3H]-dexamethasone failed to demonstrate high-affinity binding of these steroids to proteins. Exchange assay of [3H]-cortisol in high-salt nuclear extracts indicated an association constant Ka = 1.9 X 10(4) M-1 for intestinal mucosa and 2.1 X 10(4) M-1 for liver. In sea water-adapted trout, the association constant remained the same as in fresh water. These results extend previous observations obtained on the cytosol which showed that no high-affinity receptors could be disclosed in fish tissues using these two corticosteroids.
Steroids 1984 Apr
PMID:Nuclear binding of cortisol in intestinal mucosa and liver of a teleost fish (Salmo gairdnerii irideus). 652 51

For the study of hepatic bile acid transport in vivo, a series of modified bile salts were synthesized. The N-cholyl derivatives of L-leucine, L-alanine, D-alanine, beta-alanine, L-proline, and gamma-amino-butyric acid were prepared from cholic acid, ethyl chloroformate and the corresponding amino acid. Structural analysis of products was carried out mainly by electron impact mass spectrometry (20 eV) of the methyl ester/acetate derivatives. In all EI spectra, fragments in the lower mass region included McLafferty rearrangement ions (beta-cleavage) and product ions of gamma-cleavage in the vicinity of the amide linkage. In the upper mass region, fragmentation was characterized by consecutive eliminations of ketene and/or acetic acid from low intensity molecular ions. The purity of the products and their molecular weights were checked by a novel ionization technique in mass spectrometry, fast atom bombardment (FAB) mass spectrometry. FAB spectra were obtained from underivatized bile salts. The spectra were characterized by ions formed by attachment of a proton or an alkali ion to the bile salt to give intense M+H, M+Na, or M+K ions, which then showed little fragmentation.
Steroids 1983 Feb
PMID:Synthesis and spectroscopic analysis of modified bile salts. 665 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

Rat skeletal muscle cytosol proteins bound 3H-diethylstilbestrol (3H-DES). More than 90% of this binding was high capacity and low affinity. Serum albumin accounted for roughly 50-60% of the binding, as evidenced by its precipitation with anti-rat albumin IgG. About half of the binding was distinguishable from albumin and other serum proteins by its precipitation in 40% saturated ammonium sulfate. This material sedimented at 4-5S in high-salt sucrose gradients, and resolved into two components (8S and 4-5S) in low-salt. Following incubation at 23-27 degree C for one hour, 2% of the bound 3H-DES in whole cytosol (approximately 2 fmole/Mg cytosol protein) was retained by DNA cellulose, and was eluted with 0.6 M KCl. This small fraction of the total binding was inhibited by estrogens and DES analogues: estradiol-17 beta, DES, dienestrol, and hexestrol were strong inhibitors; isodienestrol, dimethylstilbestrol, estradiol-17 alpha, estrone, tamoxifen, MER-25, CI-628, and nafoxidine were weak inhibitors; dihydrotestosterone, testosterone, and prednisone did not compete. These observations indicate that specific estrogen-binding sites exist in rat skeletal muscle.
Steroids 1982 May
PMID:Specific cytosol binding of diethylstilbestrol in rat skeletal muscle. 675 12

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

A novel synthesis of 16 alpha-hydroxy-4-androstene-3,17-dione (3), 16 alpha-hydroxy-4-androstene-3,6,17-trione (4), 17 beta-amino-5-androsten-3 beta-o1 (10) and 17 beta-amino-4-androsten-3-one (14) is described. 16 alpha-Bromoacetoxy-4-androstene-3,17-dione (5), 16 alpha-bromoacetoxy-4-androstene-3,6,17-trione (6) and 17 beta-bromoacetylamino-4-androsten-3-one (15) were synthesized as potentially selective irreversible inhibitors of androgen aromatases. 16 alpha-Bromo-4-androstene-3,17-dione (1) and 16 alpha-bromo-4-androstene-3,6,17-trione (2) were converted to compounds 3 and 4 in 80-90% yield by controlled stereospecific hydrolysis using sodium hydroxide in aqueous pyridine. Reductive amination of 3 beta-hydroxy-5-androsten-17-one and 3-methoxy-3,5-androstadien-17-one (11) using ammonium acetate and sodium cyanohydridoborate (NaBH3CN) and a subsequent treatment with acid gave the amines 10 and 14 respectively, as a salt. The corresponding 17-imino compounds 9 and 13 were also isolated from the reaction mixtures when methanol was used as a solvent for the reaction. The 16 alpha-hydroxyl compounds 3 and 4 and the 17 beta-amino compound 14 were converted to the corresponding bromoacetyl derivatives, 5, 6, and 15, with bromoacetic acid and N,N'-dicyclohexylcarbodiimide.
Steroids 1981 Aug
PMID:Synthesis of 16 alpha-bromoacetoxy androgens and 17 beta-bromoacetylamino-4-androsten-3-one: potential affinity labels of human placental aromatase. 730 27


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