Oxysterols: 27-hydroxycholesterol and its radiolabeled analog.

Abstract:

:We describe a convenient and stereoselective route to the synthesis of 27-hydroxycholesterol. Also its radiolabeled analog, 22, 23 di [(3)H]-27-hydroxycholesterol with high specific radioactivity (55 Ci/mmol) was synthesized by this method. Julia condensation of steroidal 22-sulfone with aldehyde, led to the addition of the 23-27 carbon side chain building block to the steroid backbone. Formed in this reaction beta-hydroxysulfone moiety was reduced by sodium amalgam generate 22-23 unsaturated bond. Further reduction either by hydrogen or tritium furnished substrates for the synthesis of title compounds.

journal_name

Steroids

journal_title

Steroids

authors

D'Ambra TE,Javitt NB,Lacy J,Srinivasan P,Warchol T

doi

10.1016/s0039-128x(00)00099-4

subject

Has Abstract

pub_date

2000-07-01 00:00:00

pages

401-7

issue

7

eissn

0039-128X

issn

1878-5867

pii

S0039-128X(00)00099-4

journal_volume

65

pub_type

杂志文章

相关文献

STEROIDS文献大全
  • Steroid dynamics in the rabbit.

    abstract::Male rabbits were infused at a constant rate with 3H-androstenedione/14C-estrone (n = 5) or 3H-testosterone/14C-estradiol-17 beta (n = 3) for 3 1/2 hr and blood samples were obtained over the last hour and analyzed for radioactivity as androstenedione (A), testosterone (T), estrone (E1), estradiol-17 beta (E2 beta) an...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(84)90041-2

    authors: Bourget C,Flood C,Longcope C

    更新日期:1984-02-01 00:00:00

  • Progestin metabolism in the rhesus monkey corpus luteum.

    abstract::For the purpose of describing the pathway by which estrones are synthesized in the rhesus monkey (Macaca mulatta) corpus luteum (CL), CL were obtained during the midluteal phase of the menstrual cycle and fragments incubated with equimolar amounts of [7-3H]pregnenolone plus [4-14C]progesterone. Metabolites including 3...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(80)90019-7

    authors: Sholl SA,Wolf RC

    更新日期:1980-08-01 00:00:00

  • Analysis of the steroid binding domain of rat steroid 5alpha-reductase (isozyme-1): the steroid D-ring binding domain of 5alpha-reductase.

    abstract::We have previously shown that the photoactive 4-azasteroid, [1,2 3H]N-4(benzylbenzoyl)-3-oxo-4-aza-4-methyl-5alpha-androst an-17beta-carboxamide is an effective probe of rat steroid 5alpha-reductase (isozyme-1) (5alphaR-1). In the current investigation, PEG-fractionated (6.5%) detergent-solubilized preparations contai...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(98)00087-7

    authors: Bhattacharyya AK,Wang M,Rajagopalan K,Taylor MF,Hiipakka R,Liao S,Collins DC

    更新日期:1999-03-01 00:00:00

  • Historic reflection on steroids: Lederle and personal aspects.

    abstract::Steroid research at Lederle was initiated in 1946 and continued until about 1971. The areas of research interest involved primarily a study of delta 5,7-steroids, provitamin D3 variants, dehydroepiandrosterone variants, steroidal ketals, corticoids, and steroid conjugates. One of the principal goals was to develop nov...

    journal_title:Steroids

    pub_type: 历史文章,杂志文章

    doi:10.1016/0039-128x(92)90083-l

    authors: Bernstein S

    更新日期:1992-08-01 00:00:00

  • Side-chain modified vitamin D analogs induce rapid accumulation of VDR in the cell nuclei proportionately to their differentiation-inducing potential.

    abstract::1,25-Dihydroxyvitamin D(3) (1,25D) regulates gene transcription through a nuclear vitamin D receptor (VDR) which acts as a ligand-regulated transcription factor. Some structural vitamin D analogs (VDAs) are selective in their biological actions, because they retain cell-differentiating potential, while their calcemic ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2008.06.010

    authors: Gocek E,Kiełbiński M,Wyłób P,Kutner A,Marcinkowska E

    更新日期:2008-12-22 00:00:00

  • 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 isomeri...

    journal_title:Steroids

    pub_type: 杂志文章

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

    authors: Templeton JF,Majgier-Baranowska H,Marat K

    更新日期:2000-04-01 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

  • 21-Hydroxylation of C-11-oxygenated and C-11-deoxysteroids by perfused dog adrenals.

    abstract::The left adrenal of two female dogs were perfused with either 3 muCi [4-14C]cpd. S (2) and 45 muCi [1, 2-3H] 21-deoxycortisone (Dog I), or with 1 muCi [4-14C] 17-hydroxyprogesterone and 65 muCi [1,2-3H] 21-deoxycortisone (Dog II). In Dog I, 40% of the perfused 21-deoxycortisone was converted to cortisone and 23% of cp...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(77)90078-2

    authors: Horn H,Halperin G,Weidenfeld J,Mordohovich D,Maschler I

    更新日期:1977-08-01 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

  • Steroidogenic activity of hACTH and related peptides on the human neocortex and fetal adrenal cortex in organ culture.

    abstract::Explants prepared from the neocortex and the fetal zone of the human fetal adrenal (gestational age 13 to 18weeks) were maintained under conditions of organ culture for 7 to 9 days during which time they were exposed to hACTH and various related peptides. Corticotrophic activity was monitored by the daily release of d...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(78)90037-5

    authors: Branchaud CT,Goodyer CG,Hall CS,Arato JS,Silman RE,Giroud CJ

    更新日期:1978-04-01 00:00:00

  • The requirement for p42/p44 MAPK activity in progesterone receptor-mediated gene regulation is target gene-specific.

    abstract::Recent studies have suggested that progestins play a role in the etiology of breast cancer; however, the mechanisms by which progestins promote tumor formation/progression have not been defined. Progestin action, in target tissues such as the breast, is mediated by the progesterone receptor (PR). PR signaling is compl...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2012.12.014

    authors: Treviño LS,Bingman WE 3rd,Edwards DP,Nl W

    更新日期:2013-06-01 00:00:00

  • Study on steroidal oximinoethers: synthesis and stereostructure by NMR spectroscopy.

    abstract::The condensation of O-substituted hydroxylamines with conjugated 3-oxo-4-en steroids results in a mixture of syn-anti configurations. Syn-anti ratios are influenced by sterical hindrance between the oximino substituents (e.g. O-benzyl) and the steroidal skeleton. Stereostructures and isomeric ratios were proved by det...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(98)00111-1

    authors: Sohár P,Bodor A,Schwartz R

    更新日期:1999-04-01 00:00:00

  • Metabolism of beta-muricholic acid in man.

    abstract::Labeled beta-muricholic acid was obtained from germfree rats given [24-14C]-chenodeoxycholic acid. It was crystallized with the same unlabeled bile acid extracted from germfree rat pooled biles. Five patients fitted with a T-tube after cholecystectomy were given orally 100 mg of the bile acid. Metabolites of beta-muri...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(85)90006-6

    authors: Sacquet E,Parquet M,Riottot M,Raizman A,Nordlinger B,Infante R

    更新日期:1985-05-01 00:00:00

  • Relationship of androgens to body composition, energy and substrate metabolism and aerobic capacity in healthy, young women.

    abstract:OBJECTIVE:To evaluate the role of physiologic levels of androgens and their precursors in the regulation of body composition, energy and substrate metabolism and aerobic capacity in healthy, cycling, premenopausal women. EXPERIMENTAL:We evaluated 30 young (27±1 year) premenopausal, non-obese (23±0.5 kg/m(2)), normally...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2011.06.001

    authors: Keller JL,Casson PR,Toth MJ

    更新日期:2011-11-01 00:00:00

  • Evidence for a glucocorticoid receptor beta splice variant in the rat and its physiological regulation in liver.

    abstract::Glucocorticoids are important regulators of metabolism and immune function. Synthetic glucocorticoids are extensively used for immunosuppression/anti-inflammatory therapy. Since the glucocorticoid receptor (GR) is central to most hormone effects; its in vivo regulation will influence hormone/drug action. An alternativ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2012.11.014

    authors: DuBois DC,Sukumaran S,Jusko WJ,Almon RR

    更新日期:2013-02-01 00:00:00

  • The study of properties of immunoreactive estradiol secreted by adrenals and ovaries of immature female rats.

    abstract::Some properties of immunoreactive estradiol secreted by adrenals and ovaries of immature female rats were studied. It was shown that adrenals and ovaries of 15-day-old animals secrete approximately equal amounts of immunoreactive estradiol, with thin-layer chromatogram of immunoreactive material being identical for bo...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(92)90004-s

    authors: Tinnikov AA,Bazhan NM,Yakovleva TV

    更新日期:1992-04-01 00:00:00

  • Effect of a novel steroid (PM-9) on the inhibition of 5alpha-reductase present in Penicillium crustosum broths.

    abstract::The conversion of testosterone (T) to 5alpha-dihydrotestosterone (DHT) has been demonstrated in Penicillium crustosum broth obtained from fermented pistachios, lemons and corn tortillas. Furthermore, the presence of 5alpha-reductase enzyme, which is responsible for this conversion, has been established by electrophore...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(02)00180-0

    authors: Flores E,Cabeza M,Quiroz A,Bratoeff E,García G,Ramírez E

    更新日期:2003-03-01 00:00:00

  • 1,4-Chirality transfer via the ester enolate Claisen rearrangements in the preparation of (25R)- and (25S)-cholestenoic acids.

    abstract::Two variants of the Claisen rearrangement were evaluated for a stereoselective construction of a C-25 stereogenic center in cholestenoic acids based on 1,4-chirality transfer. Johnson orthoester Claisen rearrangement of (22R)- and (22S)-propargyl enol ethers proceeded in a highly stereoselective manner to give (25R)- ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2013.03.006

    authors: Ermolovich YV,Zhabinskii VN,Khripach VA

    更新日期:2013-07-01 00:00:00

  • Expression of estrogen receptor alpha in developing brain, ovary and shell gland of Gallus gallus domesticus: Impact of stress and estrogen.

    abstract::Estrogen plays a central role in the control of reproductive behaviour and in the regulation of neuroendocrine system. To elucidate the mechanism by which it controls the stress-modulated functions, it is important to understand how estrogenic effects are mediated. The distribution of estrogen receptor alpha (ERα) pro...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2019.03.002

    authors: Niranjan MK,Srivastava R

    更新日期:2019-06-01 00:00:00

  • Progesterone regulation of estrogen receptor in the rat uterus: a primary inhibitory influence on the nuclear fraction.

    abstract::The purpose of this study was to determine the short-term effects of progesterone action on estrogen receptor (Re) levels in the rat uterus. Ovariectomized, adrenalectomized rats were maintained on subcutaneous Silastic implants containing crystalline estradiol. Progesterone treatment with serum estradiol maintenance ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(81)90047-7

    authors: Okulicz WC,Evans RW,Leavitt WW

    更新日期:1981-04-01 00:00:00

  • Counteraction of early circulatory derangement by administration of low dose steroid treatment at the onset of established endotoxemic shock is not directly mediated by TNF-α and IL-6.

    abstract:BACKGROUND:Once a septic condition is progressing, administration of steroids in the pro-inflammatory phase of septic shock ought to yield maximal effect on the subsequent, devastating inflammatory response. Recently, a retrospective study showed that early initiation of corticosteroid therapy improved survival in sept...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2012.06.001

    authors: Söderberg E,Lipcsey M,Sjölin J,Larsson A,Eriksson MB

    更新日期:2012-09-01 00:00:00

  • Simultaneous quantification of progesterone, estrone, estradiol-17 beta and corticosterone in female American kestrel plasma.

    abstract::Progesterone, estrone, estradiol-17 beta and corticosterone were quantified simultaneously for the first time in female American kestrel (Falco sparverius) plasma. A mean level for each hormone was determined for the laying and non-laying periods of the summer (April-September), and for February. Means were comparable...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(84)90012-6

    authors: Rehder NB,Lague PC,Bird DM

    更新日期:1984-04-01 00:00:00

  • Radioimmunoassay of 16 alpha-hydroxyestrone in human urine.

    abstract::A radioimmunoassay for the quantitation of the sum of free, glucuronidated and urine is described. The method is reliable and accurate. Using this method, urinary excretion of 16 alpha-hydroxyestrone was determined in normal men, premenopausal women, and postmenopausal women. The values were compared to the urinary ex...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(89)90144-x

    authors: Naganuma H,Hershcopf RJ,Michnovicz JJ,Miyairi S,Bradlow HL,Fishman J

    更新日期:1989-01-01 00:00:00

  • Clues to the development of mechanism-based inactivators of 3 alpha-hydroxysteroid dehydrogenase: comparison of steroidal and nonsteroidal Michael acceptors and epoxides.

    abstract::A series of steroidal and nonsteroidal Michael acceptors that represent reaction products for 3 alpha-hydroxysteroid dehydrogenase were synthesized and evaluated as potential enzyme-generated inactivators. Introduction of exocyclic olefins either at C-2 or C-6 produced inhibitors with high affinity for the enzyme (0.0...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(91)90030-y

    authors: Penning TM,Thronton R,Ricigliano JW

    更新日期:1991-08-01 00:00:00

  • Unveiling the molecular mechanism of brassinosteroids: Insights from structure-based molecular modeling studies.

    abstract::Brassinosteroid (BR) phytohormones play indispensable roles in plant growth and development. Brassinolide (BL) and 24-epibrassinolide (24-epiBL) are the most active ones among the BRs reported thus far. Unfortunately, the extremely low natural content and intricate synthesis process limit their popularization in agric...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2015.09.002

    authors: Lei B,Liu J,Yao X

    更新日期:2015-12-01 00:00:00

  • Bile acid metabolism in partially hepatectomized rats.

    abstract::The bile flow and the bile acid secretion, calculated on liver weight basis, increased 12 H and 24 H after 60-70% hepatectomy and returned to the initial levels thereafter. The biliary phospholipid secretion much more increased than bile acids, but the cholesterol secretion decreased. Bile acid composition changed wit...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(85)90071-6

    authors: Fukano S,Saitoh Y,Uchida K,Akiyoshi T,Takeda K

    更新日期:1985-03-01 00:00:00

  • Prolonged progesterone treatment of endometrial epithelial cells modifies the effect of estradiol on their sensitivity to oxytocin.

    abstract::Estradiol (E2), progesterone (P4), and oxytocin (OT) are important for the initiation of luteolysis in ruminants but the mechanisms involved are still poorly understood. The objective of this study was to determine if duration of exposure of bovine endometrial epithelial cells to P4 affected the response of the cells ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(03)00094-1

    authors: Kombé A,Sirois J,Goff AK

    更新日期:2003-09-01 00:00:00

  • Cortisol metabolism and excretion in the isolated perfused rat kidney.

    abstract::The isolated perfused rat kidney allows a simultaneous kinetic study of both the renal metabolism and the urinary excretion of cortisol and its metabolites in the rat. In this system, cortisol was completely metabolized within 120 minutes. The main renal metabolites of cortisol (cortisone, 20 reduced cortisol and 20 r...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(77)90052-6

    authors: Reach G,Nakane H,Nakane Y,Auzan C,Corvol P

    更新日期:1977-11-01 00:00:00

  • New synthetic strategy for the synthesis of 24-epibrassinolide.

    abstract::The synthesis of (22E,24R)-5 alpha-ergosta-2,22-dien-6-one (2), a key intermediate to the preparation of 24-epibrassinolide (1), was achieved through the 3,6-diketone 8 in a 40% overall yield in five steps starting from ergosterol (3). ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(96)00087-6

    authors: Brosa C,Puig R,Comas X,Fernández C

    更新日期:1996-09-01 00:00:00

  • Steroidal saponins from Raphia vinifera and their cytotoxic activity.

    abstract::Phytochemical analysis of the fruits of Raphia vinifera led to the isolation of four new steroidal saponins (1-4), along with six known secondary metabolites (6-10). The structures of the isolated compounds were determined based on the analyses of NMR and mass spectrometric data, and chemical degradation reactions. Am...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2020.108724

    authors: Chi GF,Sop RVT,Mbaveng AT,Omollo Ombito J,Fotso GW,Nguenang GS,Kuete V,Efferth T,Ngadjui BT

    更新日期:2020-11-01 00:00:00