Steroid dimer formation: metal reduction of methyl androst-4-ene-3, 17-dion-19-oate.

Abstract:

:Two isomeric dimeric steroids, 3,3'-bis(methyl 3-hydroxyandrost-4-en-17-on-19-oate-3-yl), with symmetrical (alpha, alpha') and unsymmetrical structures (alpha,beta'), have been obtained by reduction of methyl androst-4-ene-3,17-dion-19-oate with zinc in aqueous acetic acid together with the major products, the isomeric methyl 5alpha- and 5beta-androst-3-en-17-on-19-oates. The structures of the dimers and unsaturated products are supported by spectroscopic methods. The symmetrical dimer was also obtained from treatment of the 4-en-3-on-19-oate ester with lithium in ammonia.

journal_name

Steroids

journal_title

Steroids

authors

Templeton JF,Majgier-Baranowska H,Marat K

doi

10.1016/s0039-128x(99)00108-7

subject

Has Abstract

pub_date

2000-04-01 00:00:00

pages

219-23

issue

4

eissn

0039-128X

issn

1878-5867

pii

S0039-128X(99)00108-7

journal_volume

65

pub_type

杂志文章

相关文献

STEROIDS文献大全
  • Effect of bile acids and estradiol on thymidine incorporation into DNA in MCF-7 and MCF-10A breast cell lines.

    abstract::Bile acid conjugates are found in human breast cyst fluid in average concentrations about 50-fold greater than those in blood. Because epidemiologic studies have linked colon and breast cancer and aberrant bile acid profiles are associated with colon cancer risk, we decided to study the influence of bile acid conjugat...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(97)00050-0

    authors: Raju U,Katz J,Levitz M

    更新日期:1997-10-01 00:00:00

  • Interleukin 2 up-regulates glucocorticoid receptor number in human peripheral blood mononuclear cells and the osteosarcoma cell line Saos-2 in vitro.

    abstract::Glucocorticoids are well-recognized modulators of immunocytes and osteoblasts via specific receptor-mediated mechanisms. We have evaluated the in vitro effect of interleukin 2 (IL-2) on the expression of glucocorticoid receptors (GRs) in peripheral blood mononuclear cells (PBMCs) obtained from healthy donors and osteo...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(98)00023-3

    authors: Sartori ML,Masera RG,Staurenghi A,Racca S,Angeli A

    更新日期:1998-05-01 00:00:00

  • Sex steroid-binding protein interacts with a specific receptor on human premenopausal endometrium membrane: modulating effect of estradiol.

    abstract::Sex steroid-binding protein receptor was detected on membranes prepared from human premenopausal endometrium. The binding of sex steroid-binding protein to membranes was specific, saturable, and high affinity. Scatchard analysis showed the presence of two binding sites at different affinities. The addition of estradio...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(91)90058-4

    authors: Fortunati N,Fissore F,Fazzari A,Berta L,Giudici M,Frairia R

    更新日期:1991-06-01 00:00:00

  • The role of calcium ions in the mechanism of ACTH stimulation of cortisol synthesis.

    abstract::Removal of free calcium ions from the incubation medium of isolated bovine adrenocortical cells with EGTA reduced basal cortisol synthesis and blocked the effects of ACTH; additional calcium restored normal steroid synthesis. Calcium channel blockers, verapamil and nitrendipine and the calmodulin antagonist, trifluope...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(85)90019-4

    authors: Davies E,Kenyon CJ,Fraser R

    更新日期:1985-06-01 00:00:00

  • Analysis of derivatised steroids by matrix-assisted laser desorption/ionisation and post-source decay mass spectrometry.

    abstract::Neutral steroids are difficult to analyse using desorption ionisation methods coupled with mass spectrometry (MS). However, steroids with an unhindered ketone group can readily be derivatised with the Girard P (GP) reagent to give GP hydrazones. Steroid GP hydrazones contain a quaternary nitrogen atom and are readily ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2005.08.002

    authors: Khan MA,Wang Y,Heidelberger S,Alvelius G,Liu S,Sjövall J,Griffiths WJ

    更新日期:2006-01-01 00:00:00

  • Prostaglandin inhibitors and the development of mung bean seedlings.

    abstract::The effect of cortisol and prostaglandin inhibitors on the growth and development of germinating mung bean, Vigna radiata L. Wilzek, cv. Jumbo was investigated. Cortisol, indomethacin, and a mixture of cortisol with aspirin, or benoxaprofen significantly increased radicle length and the number of lateral roots as comp...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(85)90052-2

    authors: Gawienowski AM,Csernus KM,Simon JE,Craker LE

    更新日期:1985-08-01 00:00:00

  • NFκB pathway is down-regulated by 1α,25(OH)(2)-vitamin D(3) in endothelial cells transformed by Kaposi sarcoma-associated herpes virus G protein coupled receptor.

    abstract::We have previously demonstrated that 1α,25 dihydroxy-vitamin D(3) (1α,25(OH)(2)D(3)) has antiproliferative effects on the growth of endothelial cells transformed by the viral G protein-coupled receptor associated to Kaposi sarcoma (vGPCR). In this work, we have investigated whether 1α,25(OH)(2)D(3) exerts its growth i...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2012.05.006

    authors: Gonzalez-Pardo V,D'Elia N,Verstuyf A,Boland R,Russo de Boland A

    更新日期:2012-09-01 00:00:00

  • Uptake and metabolism of androgens by bovine spermatozoa.

    abstract::Spermatozoa from bovine ejaculates and cauda epiditymidis were incubated with either tritiated 17 beta-hydroxy-5 alpha-androstane-3-one (DHT) or 5 alpha-androstane-3 alpha, 17 beta-diol (3 alpha-diol). Examination of the medium incubations demonstrated metabolic conversion of both DHT and 3 alpha-diol when these steri...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(78)90045-4

    authors: Djöseland O,Høglo S,Nyberg K,Hastings CD,Attramadal A

    更新日期:1978-03-01 00:00:00

  • Expression of membrane progesterone receptors (mPRs) in rat peripheral glial cell membranes and their potential role in the modulation of cell migration and protein expression.

    abstract::The role played by progestogens in modulating Schwann cell pathophysiology is well established. Progestogens exert their effects in these cells through both classical genomic and non-genomic mechanisms, the latter mediated by the GABA-A receptor. However, there is evidence that other receptors may be involved. Membran...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2017.09.009

    authors: Castelnovo LF,Magnaghi V,Thomas P

    更新日期:2019-02-01 00:00:00

  • 17 Beta-hydroxysteroid dehydrogenase in human breast cancer: analysis of kinetic and clinical parameters.

    abstract::In this study, we assessed the rate of estradiol degradation via the 17 beta-hydroxysteroid dehydrogenase (HSD) enzyme in breast tumors from postmenopausal women. We initially studied the effects of time, level of enzyme activity, amount of tissue assayed, and substrate concentration on the linearity of conversion of ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(88)90020-7

    authors: Leszczynski D,Santner SJ,Feil PD,Santen RJ

    更新日期:1988-03-01 00:00:00

  • Progesterone and 17 alpha-OH-progesterone in concentrations similar to that of preovulatory follicular fluid is without effect on resumption of meiosis in mouse cumulus enclosed oocytes cultured in the presence of hypoxanthine.

    abstract::Some intermediates in the cholesterol biosynthesis between lanosterol and cholesterol are capable of inducing resumption of meiosis in cultured mouse oocytes without the presence of gonadotropins. The mechanism by which these so-called Meiosis Activating Sterols (MAS) activate the meiotic process is unknown, and it is...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(02)00041-7

    authors: Yding Andersen C,Byskov AG

    更新日期:2002-11-01 00:00:00

  • Mechanistic aspects of rearrangement of 16alpha-hydroxy-17-keto steroids to the 17beta-hydroxy-16-keto isomers.

    abstract::The mechanistic aspects of the alkali-catalyzed rearrangement of 16alpha-hydroxy-17-keto steroid 1 to 17beta-hydroxy-16-keto steroid 2 are elucidated by use of (18)O- and deuterium-labeling experiments. The (18)O-labeling experiments refute the gem-hydration-quasi-diaxial dehydration mechanism for the rearrangement pr...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2008.03.001

    authors: Numazawa M,Nagaoka M,Matsuzaki H,Yamashita K,Komatsu S,Osawa Y

    更新日期:2008-09-01 00:00:00

  • Catalytic cyclometallation in steroid chemistry IV: Efficient method for the synthesis of tetrahydrothiophene, tetrahydroselenophen and cyclopentanone derivatives of (5α)-cholestane.

    abstract::Catalytic cycloalumination of (3β,5α)-3-vinylcholestane and (3α,5α)-3-allylcholestane with Et3Al catalyzed by Cp2ZrCl2 was performed for the first time to give previously unknown aluminacyclopentanes in ∼90% yield; these products were converted in situ to carbo- and heterocyclic (5α)-cholestane derivatives. ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2016.01.015

    authors: D'yakonov VA,Tuktarova RA,Islamov II,Khalilov LM,Dzhemilev UM

    更新日期:2016-04-01 00:00:00

  • Prostate cancer cell type-specific involvement of the VDR and RXR in regulation of the human PTHrP gene via a negative VDRE.

    abstract::Parathyroid hormone-related protein (PTHrP) increases the growth and osteolytic potential of prostate cancer cells, making it important to control PTHrP expression in these cells. We show that 1,25-dihydroxyvitamin D3 (1,25(OH)2D3) and its non-hypercalcemic analog, EB1089, decrease PTHrP mRNA and cellular protein leve...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2005.08.009

    authors: Sepulveda VA,Weigel NL,Falzon M

    更新日期:2006-02-01 00:00:00

  • Investigation of pH and substituent effects on the distribution ratio of novel steroidal ring D- and A-fused arylpyrazole regioisomers and evaluation of their cell-growth inhibitory effects in vitro.

    abstract::Novel androstanopyrazoles have been efficiently synthesized from steroidal β-ketoaldehydes with different arylhydrazine hydrochlorides both under acidic and basic conditions. Knorr-type transformations of 16-hydroxymethylene-dehydroepiandrosterone containing its 1,3-dicarbonyl moiety on ring D, proved to be regioselec...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2017.08.003

    authors: Baji Á,Kovács F,Mótyán G,Schneider G,Wölfling J,Sinka I,Zupkó I,Ocsovszki I,Frank É

    更新日期:2017-10-01 00:00:00

  • Bioavailability and structural study of 20-hydroxyecdysone complexes with cyclodextrins.

    abstract::20-Hydroxyecdysterone - (2β,3β,5β,22R)-2,3,14,20,22,25-hexahydroxycholest-7-en-6-one was isolated in satisfactory yield using ethanol extraction from the aerial part of Silene wolgensis (Hornem.) Otth; sometimes Silene wolgensis (Willd.) Bess. ex Spreng. The complexation of the phytoecdysteroid with β-cyclodextrin was...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2018.11.007

    authors: Temirgaziyev BS,Kučáková K,Baizhigit YA,Jurášek M,Džubák P,Hajdúch M,Dolenský B,Drašar PB,Tuleuov BI,Adekenov SM

    更新日期:2019-07-01 00:00:00

  • Caveolin-Na/K-ATPase interactions: role of transmembrane topology in non-genomic steroid signal transduction.

    abstract::Progesterone and its polar metabolite(s) trigger the meiotic divisions in the amphibian oocyte through a non-genomic signaling system at the plasma membrane. Published site-directed mutagenesis studies of ouabain binding and progesterone-ouabain competition studies indicate that progesterone binds to a 23 amino acid e...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2012.04.012

    authors: Morrill GA,Kostellow AB,Askari A

    更新日期:2012-09-01 00:00:00

  • Neuroprotective-neurotrophic effect of endogenous dehydroepiandrosterone sulfate during intense stress exposure.

    abstract::Recent reports demonstrate neurotrophic properties of dehydroepiandrosterone sulfate (DHEAS) in men at rest, as well as profound neurotrophic responses to stress in both men and women. Little is known of neuroprotective-neurotrophic effects of DHEAS during stress exposure, either in men or women. This translational st...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2014.05.011

    authors: Taylor MK,Stone M,Laurent HK,Rauh MJ,Granger DA

    更新日期:2014-09-01 00:00:00

  • An analysis of the metabolites of progesterone produced by isolated Sertoli cells at the onset of gametogenesis.

    abstract::Sertoli cells isolated from 17 day old rats were maintained in culture and incubated with [14C]-progesterone for 20 h. The cells and media were extracted with ether/chloroform and the extracts chromatographed two-dimensionally on TLC and the radioactive metabolites visualized by autoradiography. Nine of the metabolite...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(80)80009-2

    authors: Wiebe JP,Tilbe KS,Buckingham KD

    更新日期:1980-05-01 00:00:00

  • Binding specificity of medroxyprogesterone acetate and proligestone for the progesterone and glucocorticoid receptor in the dog.

    abstract::The use of the synthetic progestin medroxyprogesterone acetate (MPA) for estrus prevention in the dog can result in overproduction of growth hormone, suppression of plasma glucocorticoid levels, and the induction of mammary tumors. Proligestone (PROL) was claimed to be devoid of these unwanted side effects. In the pre...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(95)00216-d

    authors: Selman PJ,Wolfswinkel J,Mol JA

    更新日期:1996-03-01 00:00:00

  • Comparison of plasma corticosterone- and progesterone-binding activity in rat and human.

    abstract::Corticosterone-and progesterone-binding activity were measured by saturation analysis, with dextran-charcoal separation, in plasma obtained from male and female rats, and a normal male and female human. In plasma from normal male and female rats, progesterone was much less effective than corticosterone in displacing 3...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(80)90009-4

    authors: Calvano SE,Reynolds RW,Keith LD

    更新日期:1980-09-01 00:00:00

  • Fungal sterol C22-desaturase is not an antimycotic target as shown by selective inhibitors and testing on clinical isolates.

    abstract::Inhibition of concise enzymes in ergosterol biosynthesis is one of the most prominent strategies for antifungal chemotherapy. Nevertheless, the enzymes sterol C5-desaturase and sterol C22-desaturase, which introduce double bonds into the sterol core and side chain, have not been fully investigated yet for their potent...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2015.05.004

    authors: Müller C,Binder U,Maurer E,Grimm C,Giera M,Bracher F

    更新日期:2015-09-01 00:00:00

  • High concentrations of conjugated bile acids inhibit bacterial growth of Clostridium perfringens and induce its extracellular cholylglycine hydrolase.

    abstract::To investigate the effects of conjugated bile acid on bacterial growth and cholylglycine hydrolase activity, Clostridium perfringens from human feces was exposed to varying concentrations of taurine- or glycine-conjugated chenodeoxycholic acid. Extracellular enzyme activity was determined by deconjugation of radiolabe...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(94)90062-0

    authors: Kishinaka M,Umeda A,Kuroki S

    更新日期:1994-08-01 00:00:00

  • Improved synthesis of 3 alpha, 7 alpha, 12 alpha, 24 = xi-tetrahydroxy-5 beta-cholestan-26-oic acid.

    abstract::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 chloroch...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(82)90140-4

    authors: Batta AK,Tint GS,Dayal B,Shefer S,Salen G

    更新日期:1982-06-01 00:00:00

  • The 11 beta-hydroxysteroid dehydrogenase type II enzyme: biochemical consequences of the congenital R337C mutation.

    abstract::The 11 beta-hydroxysteroid dehydrogenase type II enzyme (11 beta HSD2) converts cortisol to cortisone, allowing the non-selective mineralocorticoid receptor to bind aldosterone. When the activity of this enzyme is compromised, as occurs in licorice intoxication or in the congenital syndrome of apparent mineralocortico...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(96)00013-x

    authors: Ferrari P,Obeyesekere VR,Li K,Andrews RK,Krozowski ZS

    更新日期:1996-04-01 00:00:00

  • Evidence for macromolecular synthesis in stimulation of the estrogen synthesizing system of the immature rat ovary by PMS.

    abstract::Exposure of immature rat ovaries to pregnant mare's serum gonadotropin (PMS) results in a prompt increase in testosterone and progesterone output but synthesis of estradiol (E2) increases only after a lag period of several hours. Actinomycin D (Act-D) given with PMS did not inhibit testosterone or progesterone product...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(77)90004-6

    authors: Soewoto H,Cheng HC,Johnson DC

    更新日期:1977-03-01 00:00:00

  • Mass spectrometry of ring D hydroxylated 3-methoxy-1,3,5(10)-estratrienes.

    abstract::Mass spectra and fragmentation patterns of the epimeric 17-, 16-, 15- and 14-hydroxy derivatives of 3-methoxy-1,3,5(10)-estratriene are compared. The main fragmentation pathways are differently influenced, depending on the position of the hydroxy group. The different configuration of the hydroxy groups is reflected on...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(80)90077-x

    authors: Schade W,Ihn W,Vokoun J,Schönecker B,Schubert G

    更新日期:1980-11-01 00:00:00

  • Preparation and characterization of (24R and 24S)-5beta-cholestane-3alpha,7alpha,24,25-tetrols and (24R and 24S)-5beta-cholestane-3alpha,24,25-triols.

    abstract::(24R and 24S)-5beta-cholestane-3alpha,7alpha,24,25-tetrols were prepared by osmium tetroxide oxidation of 5beta-cholest-24-ene-3alpha,7alpha-diol. The resulting diastereomeric tetrols were separated by thin-layer chromatography, their purity ascertained by melting point, gas-liquid chromatography and mass spectra and ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(78)90022-3

    authors: Batta AK,Dayal B,Tint GS,Shefer S,Toome V,Salen G,Mosbach EH

    更新日期:1978-01-01 00:00:00

  • 17-Hydroxyprogesterone metabolism in the monkey fetal adrenal: C17-20lyase and 21-hydroxylase activities.

    abstract::C17-20Lyase and 21-hydroxylase activities were measured during late gestation in the rhesus monkey (Macaca mulatta) fetal adrenal. Activities were assessed in 10,000 x g supernatants with 17-hydroxyprogesterone and NADPH as substrates. Although conversion of [14C]17-hydroxyprogesterone to [14C]androstenedione was note...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(81)90036-2

    authors: Sholl SA

    更新日期:1981-08-01 00:00:00

  • Estrogen modulation of K(+) channel activity in hypothalamic neurons involved in the control of the reproductive axis.

    abstract::Here we report on the progress we have made in elucidating the mechanisms through which estrogen alters synaptic responses in hypothalamic neurons. We examined the modulation by estrogen of the coupling of various receptor systems to inwardly rectifying and small conductance, Ca(2+)-activated K(+) (SK) channels. We us...

    journal_title:Steroids

    pub_type: 杂志文章,评审

    doi:10.1016/s0039-128x(01)00181-7

    authors: Kelly MJ,Rønnekleiv OK,Ibrahim N,Lagrange AH,Wagner EJ

    更新日期:2002-05-01 00:00:00