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Results for “Estranes”

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At least 19 recordsLinked to original sources
PubMed1989

11 beta-nitrate estrane analogues: potent estrogens.

Various estrane derivatives 1 reacted with cerium ammonium nitrate (CAN) selectively and efficiently to provide 9 alpha,11 beta-defunctionalized derivatives 2, which were subsequently deoxygenated at C-9 with triethylsilane/boron trifluoride etherate to the desired target 11 beta-nitratoestranes 3a, 3b, and 5. When examined for estrogenic and postcoital antifertility activity, 11 beta-nitrates 2c, 2d, and 3b most notably displayed more potent oral activity than did ethynylestradiol.

Animals↗
PubMed2006

4-(3'alpha15'beta-dihydroxy-5'beta-estran-17'beta-yl)furan-2-methyl alcohol: an anti-digoxin agent with a novel mechanism of action.

The synthesis and some pharmacological properties of 4-(3'alpha-15'beta-dihydroxy-5beta-estran-17'beta-yl)furan-2-methyl alcohol (16) have been described. The compound was synthesized by reacting a synthetic 3alpha- benzyloxy-5beta-estr-15-en-17-one with the ethylene acetal of 4-bromo-2-furancarboxyaldehyde, followed by hydrolysis of the ethylene acetal and reduction of the aldehyde. Despite its resemblance to the structure of cardiac steroids (CS), 16 does not bind to the CS receptor on Na(+),K(+)-ATPase and does not increase the force of contraction of heart muscle. However, 16 inhibited the digoxin-induced increase in the force of contraction and arrhythmias in guinea pig papillary muscle and human atrial appendages. The steroid also inhibited digoxin-induced alteration in endocytosed membrane traffic, indicating a novel mechanism of action.

Animals↗
PubMedDate not supplied

Correlation between retention and 1-octanol-water partition coefficients of some estrane derivatives in reversed-phase thin-layer chromatography.

The retention constants (RM) of a series of estrane and secoestrane derivatives are experimentally determined on C18-modified silica gel layers with methanol-water mobile phases of various concentrations. The slopes (m) and intercepts (RMW) of the linear relationships between RM and the volume fraction of methanol are calculated. Both constants increase when the retention of compounds increases, and there is a linear dependence between them indicating their additivity; they represent the sums of particular retention contributions of skeleton and substituents. The contributions, particularly the retention fragmental constants, are calculated by combining the linear relationships RM/log P, RM/m, and RMW/log P. The log P values of the compounds and skeleton were calculated using Rekker's fragmental constants.

1-Octanol↗
PubMed1983

HPLC-RIA of a metabolite of norethindrone in human plasma, 17 alpha-ethinyl-5 beta-estrane-3 alpha, 17 beta-diol, following conjugate hydrolysis.

An HPLC-RIA method for the assay of a reduced metabolite of norethindrone, 17 alpha-ethinyl-5 beta-estrane-3 alpha, 17 beta-diol, is described. Conjugated metabolites were extracted from human plasma and subjected to hydrolysis prior to analysis. With a daily dose of 2 mg of norethindrone, the mean plasma level of the metabolite was 24.8 ng/ml with a range of 22.8 ng/ml to 33.9 ng/ml.

Chromatography, High Pressure Liquid↗
PubMed1983

Substituted derivatives of A-nor-5 alpha-androstane and A-nor-5 alpha-estrane--structure and affinity for hormonal receptors.

The interactions of A-nor-5 alpha-androstane and A-nor-5 alpha-estrane derivatives with the estrogen and androgen receptors, have been evaluated by measuring their relative binding affinities (RBAs), under two sets of incubation conditions in order to discriminate between potent agonists from weak agonists with potential antagonist activities. Surprisingly some of these compounds which do not possess a phenolic hydroxyl group interact somewhat markedly with the estrogen receptor. This interaction is characteristic of weak estrogens, with potential anti-estrogenic activity (RBA values decreasing when increasing time and temperature of incubation). Results are in good agreement with data obtained in vivo. Moreover, some of these compounds interact also to some extent with the androgen receptor. Results will be discussed in order to outline some structure-activity relationships in these series.

Animals↗
PubMed1999

17alpha-ethyl-5beta-estrane-3alpha, 17beta-diol, a biological marker for the abuse of norethandrolone and ethylestrenol in slaughter cattle.

The metabolism of the illegal growth promoter ethylestrenol (EES) was evaluated in bovine liver cells and subcellular fractions of bovine liver preparations. Incubations with bovine microsomal preparations revealed that EES is extensively biotransformed into norethandrolone (NE), another illegal growth promoter. Furthermore, incubations of monolayer cultures of hepatocytes with NE indicated that NE itself is rapidly reduced to 17alpha-ethyl-5beta-estrane-3alpha, 17beta-diol (EED). In vivo tests confirmed that, after administration of either EES or NE, EED is excreted as a major metabolite. Therefore, it was concluded that, both in urine and faeces samples, EED can be used as a biological marker for the illegal use of EES and/or NE. Moreover, by monitoring EED in urine or faeces samples, the detection period after NE administration is significantly prolonged. These findings were further confirmed by three cases of norethandrolone abuse in a routine screening program for forbidden growth promoters.

Animal Husbandry↗
PubMed2006

Letter: steric effects in electrospray-tandem mass spectrometry of 11betanitrates of estrane series.

The fragmentation of [M+Na](+) ions produced from steroid 11beta-nitrates during electrospray/ionization (ESI) was studied by using ion trap MS/MS technique. The [M+Na](+) ions eliminate NO(2) and HNO(3) for epimers bearing 9beta and 9alpha substituents, respectively. As the main fragmentation pathways are determined mainly by the configuration at C-9 and alternative fragmentation does not practically occur, this offers the possibility for the determination of the configuration at chiral C-9 centre in the estrane 11beta-nitrate series by ESI mass spectrometry.

Letter↗
PubMed2005

Benzothieno and benzofurano annelated estranes.

The preparation of estrone derived benzothieno- and benzofurano fused steroids is described. Keystep is an intramolecular thienyl(/furyl)-ene-yne cyclization of 16-ethynyl-17-heterarylestra-1,3,5(10),16-tetraenes. The cyclization was carried out under Pt as well as under Ru catalysis.

Azo Compounds↗