Synthesis of metabolic intermediates of diethylstilbestrol.

Abstract:

:This report details the synthesis of 1) 3,4,4'-trihydroxy-alpha, alpha'-diethyl-trans-stilbene; 2) 3,4-bis-(p-hydroxyphenyl)-trans-3-hexenol; 3) 3,4-bis-(p-hydroxyphenyl)-2,4-cis,cis-hexadienol; 4) 3,4-bis-(3'-methoxy-4'-hydrophenyl)-trans-3-hexene; 5) 3,4-bis-(3',4'-dimethoxyphenyl)-trans-3-hexene. These compounds are suspected metabolites of diethylstilbestrol.

journal_name

Steroids

journal_title

Steroids

authors

Hill KA,Peterson DM,Damodaran KM,Rao PN

doi

10.1016/s0039-128x(81)90304-4

subject

Has Abstract

pub_date

1981-03-01 00:00:00

pages

327-43

issue

3

eissn

0039-128X

issn

1878-5867

pii

S0039-128X(81)90304-4

journal_volume

37

pub_type

杂志文章

相关文献

STEROIDS文献大全
  • Interaction between mineralocorticoid receptor and cAMP/CREB signaling.

    abstract::Besides regulating water and electrolyte homeostasis, the mineralocorticoid receptor (MR) elicits pathophysiological effects in the renocardiovascular system. Although the MR's closest relative, the glucocorticoid receptor (GR), acts as a transcription factor at the same hormone-response-element (HRE), activated gluco...

    journal_title:Steroids

    pub_type: 杂志文章,评审

    doi:10.1016/j.steroids.2009.10.006

    authors: Grossmann C,Ruhs S,Seiferth A,Gekle M

    更新日期:2010-08-01 00:00:00

  • Development of a new sensitive and specific time-resolved fluoroimmunoassay (TR-FIA) of chlormadinone acetate in the serum of treated menopausal women.

    abstract::We describe the development of a serum chlormadinone acetate (CMA) time-resolved fluoroimmunoassay (TR-FIA). We prepared haptens (3-CMO-chlormadinone acetate and 6-chloropregna-4,6-dien-17,20-diol-3-one-20-hemisuccinate), biotinylated tracers (3(biotinylaminopropylamido) 3-CMO-chlormadinone acetate and 3-(6-chloropreg...

    journal_title:Steroids

    pub_type: 临床试验,杂志文章

    doi:10.1016/s0039-128x(02)00050-8

    authors: Fiet J,Giton F,Auzerie J,Galons H

    更新日期:2002-12-01 00:00:00

  • LC/ESI-MS/MS analysis of urinary 3β-sulfooxy-7β-N-acetylglucosaminyl-5-cholen-24-oic acid and its amides: new biomarkers for the detection of Niemann-Pick type C disease.

    abstract::We developed a sensitive, reliable, and accurate LC/ESI-MS/MS method for measurement of 3β-sulfooxy-7β-N-acetylglucosaminyl-5-cholen-24-oic acid and its glycine and taurine amides in urine. This atypical C24 bile acid has been reported previously to be present in the urine of patients with Niemann-Pick Type C (NPC) di...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2013.05.017

    authors: Maekawa M,Misawa Y,Sotoura A,Yamaguchi H,Togawa M,Ohno K,Nittono H,Kakiyama G,Iida T,Hofmann AF,Goto J,Shimada M,Mano N

    更新日期:2013-10-01 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

  • Synthesis and biological evaluation of novel sarsasapogenin derivatives as potential anti-tumor agents.

    abstract::Based on the fact that timosaponin A-III (TA-III) exhibits potent cytotoxic effects and has been considered as a potential anti-tumor agent, a range of novel sarsasapogenin derivatives 1, 2a-2g, 3, 4, 5, 6a-6g have been synthesized by a simple and facile synthetic route. The in vitro cytotoxic activity of these synthe...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2014.09.007

    authors: Yin Y,Zhao XC,Wang SJ,Gao PY,Li LZ,Ikejima T,Song SJ

    更新日期:2015-01-01 00:00:00

  • Simultaneous quantification of GABAergic 3alpha,5alpha/3alpha,5beta neuroactive steroids in human and rat serum.

    abstract::The 3alpha,5alpha- and 3alpha,5beta-reduced derivatives of progesterone, deoxycorticosterone, dehydroepiandrosterone and testosterone enhance GABAergic neurotransmission and produce inhibitory neurobehavioral and anti-inflammatory effects. Despite substantial information on the progesterone derivative (3alpha,5alpha)-...

    journal_title:Steroids

    pub_type: 临床试验,杂志文章

    doi:10.1016/j.steroids.2008.12.015

    authors: Porcu P,O'Buckley TK,Alward SE,Marx CE,Shampine LJ,Girdler SS,Morrow AL

    更新日期:2009-04-01 00:00:00

  • Development of potent non-estrogenic estrone sulfatase inhibitors.

    abstract::Estrogen levels in breast tumors of post-menopausal women are as much as 10 times higher than estrogen levels in plasma, presumably due to in situ formation of estrogen. The major source of estrogen in breast cancer cells may be conversion of estrone sulfate to estrone by the enzyme estrone sulfatase. Thus, inhibitors...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(98)00044-0

    authors: Li PK,Chu GH,Guo JP,Peters A,Selcer KW

    更新日期:1998-07-01 00:00:00

  • Hormone mediated changes in monoamine stores and regulation of enzymes of biosynthesis and metabolism in the rat adrenal gland. Influence of progesterone, estradiol, ACTH and testosterone administration.

    abstract::The influence of daily injections, for 7 days, of 17-hydroxyprogesterone caproate (8 mg/100 g body weight pro die), of estradiol-17 beta 17-undecylate (1.2 mg/100 g body weight pro die) of testosterone enanthate (2 mg/100 g body weight pro die) and of ACTH (4 IU/100 g body weight pro die) to male Wistar rats, weighing...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(81)90016-7

    authors: Bukhari AR,Guessab A,Nicol ML

    更新日期:1981-07-01 00:00:00

  • The sulfoconjugation of androstenone and dehydroepiandrosterone by human and porcine sulfotransferase enzymes.

    abstract::Porcine sulfotransferase 2A1 (pSULT2A1) is a key enzyme involved in the testicular and hepatic sulfoconjugation of steroids such as dehydroepiandrosterone (DHEA) and potentially androstenone. This latter steroid is a major cause of boar taint, which is an unpleasant off-odour and off-flavour in pork from male pigs. Su...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2018.05.010

    authors: Laderoute H,Bone C,Squires EJ

    更新日期:2018-08-01 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

  • Urinary free cortisol and androgens in the population-Hormone interactions and the relationship with body composition and bone status.

    abstract:OBJECTIVE:Abnormal secretion of thyroid hormones, growth hormone, cortisol and androgens influences body composition. We hypothesised that higher cortisol excretion, in combination with higher androgen and IGF-I concentrations, had a synergistic, favourable effect on body mass and bone. DESIGN, PATIENTS AND METHODS:Th...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2016.09.006

    authors: Ragnarsson O,Trimpou P,Oleröd G,Landin-Wilhelmsen K

    更新日期:2016-11-01 00:00:00

  • Human mammary tumor cell proliferation: primary role of platelet-derived growth factor and possible synergism with human alpha-fetoprotein.

    abstract::Human mammary medullary carcinoma cells (passages 16 to 21) were cultured for 2 days to allow for attachment, followed by 6 days of culture in either fetal calf serum, human cord blood, human amniotic fluid, or growth factors in the presence or absence of purified human alpha-fetoprotein (AFP). When growth factors wer...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(91)90042-t

    authors: Leal JA,Gangrade BK,Kiser JL,May JV,Keel BA

    更新日期:1991-05-01 00:00:00

  • Diacetoxyiodobenzene-mediated synthesis of unnatural furospirostane sapogenins derived from diosgenin and tigogenin.

    abstract::Two unnatural steroid sapogenins bearing a furospirostane side chain were prepared starting from the readily available spirostane sapogenins, tigogenin and diosgenin following a synthetic protocol that included: (i) introduction of a carbonyl group at position C-23, (ii) diacetoxyiodobenzene-induced F-ring contraction...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2013.05.013

    authors: Sánchez-Flores J,Romero-Ávila M,Rosado-Abón A,Flores-Álamo M,Iglesias-Arteaga MA

    更新日期:2013-09-01 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

  • Effects of acrolein on the production of corticosterone in male rats.

    abstract::Acrolein, an α, β-unsaturated aldehyde, exists in a wide range of sources. Acrolein can be not only generated from all types of smoke but also produced endogenously from the metabolism by lipid peroxidation. The cellular influence of acrolein is due to its electrophilic character via binding to and depleting cellular ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2016.03.009

    authors: Yeh YH,Chou JC,Weng TC,Lieu FK,Lin JY,Yeh CC,Hu S,Wang PS,Idova G,Wang SW

    更新日期:2016-07-01 00:00:00

  • Rat and human embryo and post-natal sera contain a potent endogenous competitor of estrogen-rat alpha-fetoprotein interactions.

    abstract::A highly active inhibitor of the binding of estrone and estradiol-17beta to rat alpha-fetoprotein is demonstrated for the first time in embryo, immature and adult rat sera as well as in fetal and adult human sera. The competitive character and the narrow specificity of this inhibition effect is shown. The major compou...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(77)80023-8

    authors: Benassayag C,Vallette G,Delorme J,Savu L,Nunez EA,Jayle MF

    更新日期:1977-12-01 00:00:00

  • Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults.

    abstract::Two-hydroxyestrone (2OHE-1) and 16alpha-hydroxyestrone (16OHE-1) are two estrogen metabolites that may play important roles in the development or promotion of breast cancer. Our study assessed the reliability of a newly developed kit procedure for measuring 2OHE-1. Although under certain conditions the assay would not...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(00)00139-2

    authors: Spierto FW,Gardner F,Smith SJ

    更新日期:2001-01-01 00:00:00

  • Steroid hormone feedback on LH in prepubertal Holstein heifers.

    abstract::A significant dose-response relationship between gonadotropin-releasing hormone (GnRH) and time to luteinizing hormone (LH) peak, peak serum LH and total serum LH was obtained in prepubertal Holstein heifers (28 weeks of age) (Experiment 1). For the second experiment, the effect of steroid feedback on the anterior pit...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(86)90082-6

    authors: Swanson LV,McCarthy SK

    更新日期:1986-02-01 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

  • Hepatic metabolism of 3-oxoandrost-4-ene-17 beta-carboxylic acid in the adult rat: formation of carboxyl-linked glucuronides both in vivo and in vitro.

    abstract::The hepatic metabolism of 3-oxoandrost-4-ene-17 beta-carboxylic acid (etienic acid), a probable acidic catabolite of deoxycorticosterone, was investigated using rats prepared with an external biliary fistula. Metabolic products were identified by GC-MS after hydrolysis with beta-glucuronidase and by proton nuclear mag...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(92)90052-b

    authors: Radominska A,Little JM,Lester R,St Pyrek J

    更新日期:1992-07-01 00:00:00

  • Highly sensitive determination of estrone and estradiol in human serum by liquid chromatography-electrospray ionization tandem mass spectrometry.

    abstract::A highly sensitive and specific quantification method of estrone and estradiol in human serum was described based upon the use of picolinoyl derivatization and liquid chromatography-electrospray ionization mass spectrometry (LC-ESI-MS) in a positive mode. Estrogens were treated with picolinoyl chloride hydrochloride o...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2007.07.003

    authors: Yamashita K,Okuyama M,Watanabe Y,Honma S,Kobayashi S,Numazawa M

    更新日期:2007-10-01 00:00:00

  • Alterations in the androgen metabolism of the female guinea-pig during pregnancy.

    abstract::The peripheral conversion of testosterone (T) into androstenedione (delta 4) and dihydrotestosterone (DHT) were studied in pregnant (days 32, 48 and 67 post coitum) and non-pregnant anesthetized guinea-pigs by constant intravenous infusion of tritium labeled T. Endogenous levels were measured by radioimmunoassay, and ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(83)90157-5

    authors: Despres G,Rigaudière N

    更新日期:1983-08-01 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

  • The synthesis and biological activity of 22-fluorovitamin D3: a new vitamin D analog.

    abstract::We synthesized 22-fluorovitamin D3 from (22S) cholest-5-ene-3 beta, 22-diol-3 beta-acetate 2. Compound 2 was treated with diethylaminosulfur trifluoride to give 22-fluorocholest-5-en-3 beta-acetate 3 and (E) 22-dehydrocholest-5-en-3 beta-acetate. Compound 3 was treated with N-bromosuccinimide to give a mixture of the ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(86)90044-9

    authors: Gill HS,Londowski JM,Corradino RA,Kumar R

    更新日期:1986-07-01 00:00:00

  • Norethindrone acetate (NA) and ethinyl estradiol (EE) related oxidative transformation products in stability samples of formulated drug product: synthesis of authentic references.

    abstract::Preparative chemical methods for the synthesis of eight oxidative transformation products of ethinyl estradiol (EE) and norethindrone acetate (NA) are described. The prepared materials are useful as reference materials and standards for pharmaceutical analysis of EE and NA as bulk chemical or in formulated product. Al...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(01)00149-0

    authors: Ekhato IV,Hurley T,Lovdahl M,Revitte TJ,Guo L,Huang Y,Clipper S,Colson C

    更新日期:2002-03-01 00:00:00

  • Reduced urinary aldosterone excretion rates with normal plasma concentrations of aldosterone in the very elderly.

    abstract::Although aldosterone production declines with age, so does the aldosterone metabolic clearance rate (MCR), and the net effect of age on the circulating level of aldosterone may be less than can be predicted from production rates alone. The effect of age on aldosterone production and plasma levels was studied in a grou...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(88)90191-2

    authors: Pratt JH,Hawthorne JJ,Debono DJ

    更新日期:1988-01-01 00:00:00

  • Validation of a specific radioimmunoassay to measure plasma cortisol in the fetal sheep.

    abstract::A procedure utilizing co-chromatography and complementary antiserum comparisons was employed to assess the specificity of a cortisol radioimmunoassay for use in the chronically catheterized fetal sheep preparation. Complementary antiserum comparisons is a technique by which two different cortisol antisera, prepared fr...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(79)80005-7

    authors: Magyar DM,Buster JE,Elsner CW,Nathanielsz PW,Oliveros R,Abraham GE

    更新日期:1979-01-01 00:00:00

  • Synthesis and biological activity of brassinosteroids fluorinated at C-2.

    abstract::In this paper we report the synthesis of four fluorinated analogues of brassinosteroids in which fluorine was introduced stereoselectively at C-2. The bioactivity of these new compounds was evaluated using the rice lamina inclination test. The results show that two of these analogues elicit high bioactivity, suggestin...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2008.12.006

    authors: Acebedo SL,Ramírez JA,Galagovsky LR

    更新日期:2009-04-01 00:00:00

  • 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

  • Synthesis of ursodeoxycholic acid from plant-source (20S)-21-hydroxy-20-methylpregn-4-en-3-one.

    abstract::A novel synthetic route of producing ursodeoxycholic acid (UDCA) was developed through multiple reactions from cheap and commercially available bisnoralcohol (BA). The key reaction conditions, including solvents, bases and reaction temperatures of the route were investigated and optimized. In the straightforward route...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2020.108600

    authors: Wang J,Gu XZ,He LM,Li CC,Qiu WW

    更新日期:2020-05-01 00:00:00