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 chlorochromate. The second method employs diborane for the reduction of the -COOH group to the -CH2OH group, while the third method involves the reduction of 3 alpha, 7 alpha, 12 alpha-triformyloxy-5 beta-cholan-24-oic acid (as the acid chloride) directly into 3 alpha, 7 alpha, 12 alpha-triformyloxy-5 beta-cholan-24-al with TMA-ferride (tetramethylammonium hydridoirontetracarbonyl). The aldehyde obtained by any of the above methods underwent smooth Reformatsky reaction with ethyl alpha-bromopropionate to yield 3 alpha, 7 alpha, 12 alpha, 24 xi-tetrahydroxy-5 beta-cholestan-26-oic acid.

journal_name

Steroids

journal_title

Steroids

authors

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

doi

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

subject

Has Abstract

pub_date

1982-06-01 00:00:00

pages

693-702

issue

6

eissn

0039-128X

issn

1878-5867

pii

0039-128X(82)90140-4

journal_volume

39

pub_type

杂志文章

相关文献

STEROIDS文献大全
  • Increased SULT1E1 activity in HepG2 hepatocytes decreases growth hormone stimulation of STAT5b phosphorylation.

    abstract::Mouse models of cystic fibrosis (CF) display increased sulfotransferase 1E1 (SULT1E1) activity in hepatocytes of cystic fibrosis transmembrane receptor (CFTR)-deficient animals. SULT1E1 is responsible for the sulfation and inactivation of beta-estradiol (E2) at physiological concentrations. IGF-1 message levels in CFT...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2008.09.002

    authors: Li L,He D,Wilborn TW,Falany JL,Falany CN

    更新日期:2009-01-01 00:00:00

  • Synthesis of 13C-labeled steroid hormones.

    abstract::The synthesis of 13C-labeled steroid hormones is reviewed. Two general approaches are highlighted: partial synthesis in which part of the steroid nucleus is replaced with 13C-labeled synthons, and total synthesis. Examples from both approaches, leading to (3-(3)C)-, (4-(13)C)-, (3,4-(13)C2)-, and (1,2,3,4-(13)C4)- lab...

    journal_title:Steroids

    pub_type: 杂志文章,评审

    doi:10.1016/0039-128x(90)90012-z

    authors: Zomer G,Stavenuiter JF

    更新日期:1990-10-01 00:00:00

  • Plasma and urinary markers of oral testosterone undecanoate misuse.

    abstract::Orally administered testosterone undecanoate (TU), an anabolic, androgenic steroid, can potentially be abused by athletes. Indirect evidence for detecting oral TU intake could be deduced from the changes in steroid profile post-administration. Direct evidence could be obtained by detection of unchanged TU in plasma. T...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(01)00128-3

    authors: Peng SH,Segura J,Farré M,González JC,de la Torre X

    更新日期:2002-01-01 00:00:00

  • Immunochemical studies on the putative plasmalemmal receptor for 1,25-dihydroxyvitamin D3 II. Chick kidney and brain.

    abstract::Chick kidney and brain were analyzed for the subcellular distribution (if any) of a putative plasma membrane receptor for 1,25-dihydroxyvitamin D3 [1,25(OH)2D3]. Fractionation protocols were found to be based not only on differential centrifugation conditions, but also gentleness of resuspension procedures, and suffic...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(99)00030-6

    authors: Jia Z,Nemere I

    更新日期:1999-08-01 00:00:00

  • Bioassay-guided isolation and identification of anti-ulcer ecdysteroids from the seeds of Sphenocentrum jollyanum Pierre (Menispermaceae).

    abstract::Sphenocentrum jollyanum seeds (MeOH extract and n butanol fraction) exhibited urease inhibitory activity (IC50 40.0 ± 0.92, 28.6 ± 0.41). The Ethyl acetate (EtOAc) fraction gave significant antacid activity with an increase in the baseline pH value of 1.2 to 1.61 ± 0.00 and 1.53 ± 0.00 at 50 and 100 mg, respectively, ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2020.108636

    authors: Akinwumi IA,Sonibare MA,Yeye EO,Khan M

    更新日期:2020-07-01 00:00:00

  • Evidence that the maintenance of early pregnancy in the rabbit requires ""blastocyst estrogen''.

    abstract::It has been shown by others that treatment with only progesterone is sufficient to induce implantation and maintain pregnancy in ovariectomized-adrenalectomized rabbits. Based on these results, it was deduced that induction of implantation in the rabbit does not require estrogen. In making this deduction, "blastocyst ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(76)90017-9

    authors: Dey SK,Dickmann Z,Sen Gupta J

    更新日期:1976-10-01 00:00:00

  • Chromatographic patterns of urinary ethynyl estrogen metabolites in various populations.

    abstract::Radioactive mestranol (ME) and/or ethynylestradiol (EE) were administered to women in Nigeria, Sri Lanka, and the USA, and the types and patterns of radioactive urinary conjugates examined by Sephadex LH-20 chromatography. There are no differences in the total excretion of urinary radioactivity over 3 days. Consistent...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(80)90001-x

    authors: Williams MC,Goldzieher JW

    更新日期:1980-09-01 00:00:00

  • Cholesterol side chain cleavage and aromatase activities in the corpus luteum of the pregnant rhesus monkey.

    abstract::Cholesterol side-chain cleavage (CSCC) and aromatase activities were measured in luteal mitochondria and tissue pieces, respectively, from rhesus monkeys on days 22, 49, 128 and 160 of gestation. CSCC activity did not vary significantly during gestation and thus probably does not respond to chorionic gonadotropin whic...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(77)90042-3

    authors: Sholl SA,Wolf RC,Colás AE

    更新日期:1977-02-01 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

  • Aldosterone: the minority hormone of the adrenal cortex.

    abstract::In comparison with the glucocorticoids cortisol and corticosterone, the mineralocorticoid aldosterone is a minority hormone of the mammalian adrenal cortex, and its proper function is dependent upon protective physiological mechanisms. These include a particular site of aldosterone synthesis in zona glomerulosa cells ...

    journal_title:Steroids

    pub_type: 杂志文章,评审

    doi:10.1016/0039-128x(94)00021-4

    authors: Müller J

    更新日期:1995-01-01 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

  • Is gender difference in postnatal thyroid growth associated with specific expression patterns of androgen and estrogen receptors?

    abstract::Variations in sex steroids bioavailability were linked to the gender difference in the growth of thyroid glands of neonatal rats. In the present study we tested androgen receptor (AR) and estrogen receptor (ER) concentrations by ligand binding assay, and expression of their genes by RT-PCR and Western blot in the thyr...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2010.06.009

    authors: Stanley JA,Aruldhas MM,Yuvaraju PB,Banu SK,Anbalagan J,Neelamohan R,Annapoorna K,Jayaraman G

    更新日期:2010-12-12 00:00:00

  • Between basic and applied research: Ciba's involvement in steroids in the 1950s and 1960s.

    abstract::Through its collaboration with the ETH in Zurich (Ruzicka's group) and later on with the University of Basel (Reichstein's group). Ciba became involved very early in steroid chemistry. The main task of the chemists consisted at that time of the synthesis of natural hormones and their derivatives. Cholesterol served fo...

    journal_title:Steroids

    pub_type: 历史文章,杂志文章

    doi:10.1016/0039-128x(96)00040-2

    authors: Heusler K,Kalvoda J

    更新日期:1996-08-01 00:00:00

  • Development and evolution of therapies targeted to the estrogen receptor for the treatment and prevention of breast cancer.

    abstract::This article describes the origins and evolution of "antiestrogenic" medicines for the treatment and prevention of breast cancer. Developing drugs that target the estrogen receptor (ER) either directly (tamoxifen) or indirectly (aromatase inhibitors) has improved the prognosis of breast cancer and significantly advanc...

    journal_title:Steroids

    pub_type: 杂志文章,评审

    doi:10.1016/j.steroids.2006.10.009

    authors: Jordan VC,Brodie AM

    更新日期:2007-01-01 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

  • Analytical strategies for the direct mass spectrometric analysis of steroid and corticosteroid phase II metabolites.

    abstract::The use of steroid hormones as growth promoters remains illegal in Europe. A classical approach used to control their utilization consists to measure the parent drug in target biological matrices. However, this strategy may fail when the parent drug is submitted to extensive metabolism reactions. For urine and tissue ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2004.11.009

    authors: Antignac JP,Brosseaud A,Gaudin-Hirret I,André F,Bizec BL

    更新日期:2005-03-01 00:00:00

  • The effects of 1alpha,24(S)-dihydroxyvitamin D(2) analog on cancer cell proliferation and cytokine expression.

    abstract::It is well established that 1alpha,25-dihydroxyvitamin D(3) (1alpha,25(OH)(2)D(3)), the active metabolite of vitamin D, plays a role in regulating proliferation and differentiation of cells, in addition to its classic function in mineral homeostasis. Recent studies have also provided evidence for the involvement of 1a...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(00)00154-9

    authors: Shany S,Levy Y,Lahav-Cohen M

    更新日期:2001-03-01 00:00:00

  • New pregnane glycosides from Stelmatocrypton khasianum.

    abstract::Four new pregnane glycosides, stelmatocryptonoside A, B, C, and D (1-4), were isolated from the stems of Stelmatocrypton khasianum. On the basis of chemical and spectral data, the structures of 1-4 were established as 3beta, 16alpha-dihydroxy-pregn-5-en-20-one-16-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(01)00187-8

    authors: Zhang Q,Zhao Y,Wang B,Feng R,Liu X,Cheng T

    更新日期:2002-04-01 00:00:00

  • Distribution of immunoreactive androgen-binding protein/sex hormone-binding globulin in tissues of the fetal rat.

    abstract::Androgen-binding protein/sex hormone-binding globulin (ABP/SHBG) is an extracellular carrier protein that binds androgens and estrogens with high affinity. In the adult, ABP/SHBG is thought to function in the male reproductive system and the general circulation in both sexes to modulate the actions of sex steroids. Th...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(96)00049-9

    authors: Becchis M,Sullivan PM,Ordronneau P,Petrusz P,Joseph DR

    更新日期:1996-07-01 00:00:00

  • Evidence for a new biologic pathway of androstenedione synthesis from 11-deoxycortisol.

    abstract::17-Hydroxyprogesterone is a well-known precursor of androstenedione in adrenal biosynthesis. This study using sheep adrenal incubations demonstrates that 11-deoxycortisol, the precursor of cortisol synthesis, also can be a precursor of androstenedione. Indeed, our data show that androstenedione synthesis is negatively...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(91)90112-9

    authors: Auzéby A,Bogdan A,Touitou Y

    更新日期:1991-01-01 00:00:00

  • Profiling of urinary formestane and confirmation by isotope ratio mass spectrometry.

    abstract::Formestane (F, androst-4-en-4-ol-3,17-dione) is an irreversible aromatase inhibitor with the ability to suppress the estrogen production from anabolic steroids. Consequently, F is mentioned on the World Anti-Doping Agency (WADA) prohibited list and because studies have shown that F is produced endogenously in small am...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2013.07.011

    authors: Polet M,Van Renterghem P,Van Gansbeke W,Van Eenoo P

    更新日期:2013-11-01 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

  • 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

  • Steroid delta 4-5 beta-reductase in human mammary tumors.

    abstract::Steroid delta 4-5 alpha- and delta 4-5 beta-reductase activity was determined in 16 human mammary tumors and 8 DMBA-induced rat mammary tumors using a spectrophotometric assay. Steroid delta 4-5 alpha-reductase was present in all tumors investigated while delta 4-5 beta-reductase was detected in only 6 estrogen recept...

    journal_title:Steroids

    pub_type: 历史文章,杂志文章

    doi:10.1016/s0039-128x(79)80010-0

    authors: Abul-Hajj YJ

    更新日期:1979-01-01 00:00:00

  • Synthesis, NMR and crystal characterization of dimeric terephthalates derived from epimeric 4,5-seco-cholest-3-yn-5-ols.

    abstract::Two dimeric steroidal terephthalates derived from epimeric 4,5-seco-cholest-3-yn-5-ols were prepared starting from cholesterol in a five-step synthetic sequence. X-ray crystallography shows that the obtained compounds display novel supramolecular networks in the solid state in which the facial hydrophobicity of the st...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2016.03.001

    authors: Alarcón-Manjarrez C,Arcos-Ramos R,Álamo MF,Iglesias-Arteaga MA

    更新日期:2016-05-01 00:00:00

  • A facile and efficient synthesis of some (6E)-hydroximino-4-en-3-one steroids, steroidal oximes from Cinachyrella spp. sponges.

    abstract::Using beta-sitosterol as a starting material, (6E)-hydroximino-24-ethylcholest-4-en-3-one (1), a natural steroidal oxime from Cinachyrella alloclada and C. apion, was synthesized in four steps with a high overall yield. First, beta-sitosterol (5a) is transformed into the corresponding 24-ethylcholest-4-en-3,6-dione (6...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2007.10.007

    authors: Cui J,Huang L,Fan L,Zhou A

    更新日期:2008-03-01 00:00:00

  • A facile three-component solid phase synthesis of steroidal A-ring fused pyrimidines under microwave irradiation.

    abstract::The preparation of ring-A fused pyrimidines at the steroidal 2,3-position is herein described. The novel steroidal pyrimidines were prepared from the solid phase three-component reaction of 2-hydroxymethylene-3-keto steroids, arylaldehydes and ammonium acetate under microwave irradiation. ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2009.03.006

    authors: Barthakur MG,Gogoi S,Dutta M,Boruah RC

    更新日期:2009-09-01 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

  • Synthesis and anticancer activity of novel C6-piperazine substituted purine steroid-nucleosides analogues.

    abstract::Novel C6-piperazine substituted purine nucleoside analogues (2-9) bearing a modified pyranose-like D ring of the 4-azasteroid moiety were efficiently synthesized through nucleophilic substitution at C6 position of the steroid-nucleoside precursors (1) with versatile piperazines. All newly-synthesized compounds were ev...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2013.12.004

    authors: Huang LH,Xu HD,Yang ZY,Zheng YF,Liu HM

    更新日期:2014-04-01 00:00:00

  • Synthesis and biological activities of 2 beta-chloro-, 2 beta-fluoro-, and 2 beta-methoxy-1 alpha,25-dihydroxyvitamin D3.

    abstract::Using 1 alpha,2 alpha-oxido-cholesta-5,7-diene-3 beta,25-diol (2) as a starting material, the provitamins of calcitriol with an additional 2 beta-chloro-, 2 beta-fluoro-, and 2 beta-methoxy-substituent (3,4,5) are obtained by transdiaxial opening of the oxirane ring with nucleophiles. An efficient irradiation process ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(98)00072-5

    authors: Scheddin D,Mayer H,Schönecker B,Gliesing S,Reichenbächer M

    更新日期:1998-12-01 00:00:00