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


: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, suggesting the involvement of hydrogen bond interactions between the active brassinosteroids and their cellular receptor.






Acebedo SL,Ramírez JA,Galagovsky LR




Has Abstract


2009-04-01 00:00:00
















  • A microwave promoted and Lewis acid catalysed solventless approach to 4-azasteroids.

    abstract::The preparation of 3-oxo-4-azasteroid from A-nor-3,5-secosteroid-3-oic acid is described in a solventless condition catalysed by Lewis acid under microwave irradiation. We utilized urea as an environmentally benign source for the generation of ammonia for the aza cyclization reaction. ...


    pub_type: 杂志文章


    authors: Borthakur M,Boruah RC

    更新日期:2008-07-01 00:00:00

  • Characterization of ALVA-41 cells, a new human prostatic cancer cell line.

    abstract::The ALVA-41 cell line was derived from a bony metastasis from a human prostatic carcinoma. The line has a number of distinct, advantageous properties that should make it useful as a tool for the study of prostate cancer. It grows rapidly and is easy to work with. It has receptors for androgens and glucocorticoids but ...


    pub_type: 杂志文章


    authors: Nakhla AM,Rosner W

    更新日期:1994-10-01 00:00:00

  • Gene expression in endometrial cancer cells (Ishikawa) after short time high dose exposure to progesterone.

    abstract::The potent antiproliferative effect of progestins has been utilized in clinical regimens for treatment of endometrial proliferative disorders. The progestin infiltrated intrauterine device used as therapy for endometrial carcinoma as well as endometrial hyperplasia yields a hundred-fold increase of local progestin con...


    pub_type: 杂志文章


    authors: Paulssen RH,Moe B,Grønaas H,Orbo A

    更新日期:2008-01-01 00:00:00

  • Estradiol mediates relaxation of porcine lower esophageal sphincter.

    abstract::Most pregnant women have symptoms of gastroesophageal reflux disease (GERD) during pregnancy. Postmenopausal hormone replacement therapy is associated with GERD. The effects of estradiol on lower esophageal sphincter (LES) motility and GERD are not clearly known. The purpose of this study is to investigate the effects...


    pub_type: 杂志文章


    authors: Tsai CC,Tey SL,Chang LC,Su YT,Lin KJ,Huang SC

    更新日期:2018-08-01 00:00:00

  • A facile synthesis of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol.

    abstract::A convenient procedure for the synthesis of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol via a modified homologation sequence of the intermediate 3 alpha,7 alpha,12 alpha-triformyloxy-24-oxo-25-diazo-25-homo-5 beta-cholane involving a homogeneous medium is described. This involves treating the intermediate alp...


    pub_type: 杂志文章


    authors: Dayal B,Bagan E,Speck J,Salen G

    更新日期:1980-04-01 00:00:00

  • Synthesis and purification of radioactive 6beta-iodomethyl-19-norcholest-5(10)-en-3beta-ol.

    abstract::A method for the synthesis and purification of 6beta-iodomethyl-19-norcholest-5(10)-ene-3beta-ol-131I of greater than 98 mole% chemical purity and greater than 99% radiochemical purity is presented. Carbon-13 and proton NMR were used to establish the identity and purity. Discrepancies in the characterization of this c...


    pub_type: 杂志文章


    authors: Scott KN,Couch MW,Mareci TH,Williams CM

    更新日期:1976-08-01 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...


    pub_type: 杂志文章


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

    更新日期:1989-01-01 00:00:00

  • The synthesis of androstane brassinosteroid analogues with alpha-azido acid ester groups in position 17beta.

    abstract::Androstane brassinosteroid analogues with alpha-azido acid ester groups in position 17beta were synthesized from 2alpha,3alpha,17beta-trihydroxy-5alpha-androstan-6-one after the protection of the 2alpha,3alpha-diols upon treatment with the corresponding alpha-azido acid and the subsequent deprotection of the diol grou...


    pub_type: 杂志文章


    authors: Hnilickova J,Kohout L,Capdevila E,Esteve A,Vilaplana M,Molist M,Brosa C,Swaczynova-Oklestkova J,Slavikova B

    更新日期:2010-12-01 00:00:00

  • Sex steroid hormones do not influence the oxidative burst activity of polymorphonuclear leukocytes from ovariectomized cows in vitro.

    abstract::During the periparturient period, dairy cows are subjected to physiological changes that may induce immunosuppression and an increased susceptibility of the animal to bacterial infections such as mastitis. The incidence of clinical environmental mastitis is high during the last period of gestation, at parturition and ...


    pub_type: 杂志文章


    authors: Winters KR,Meyer E,Van Merris VM,Van Den Broeck WL,Duchateau L,Burvenich C

    更新日期:2003-05-01 00:00:00

  • Five new C21 steroidal glycosides from Cynanchum komarovii Al.Iljinski.

    abstract::Five new C21 steroidal glycosides, namely, komarosides D (1), E (2), F (3), G (4), and H (5), along with two known C21 steroidal glycosides cynatratoside E (6) and hancoside A (7), were isolated from the ethanol extract of the roots of Cynanchum komarovii Al. Iljinski (Asclepiadaceae). Their structures were determined...


    pub_type: 杂志文章


    authors: Liqin W,Yuemao S,Xing X,Yuqing W,Jun Z

    更新日期:2004-05-01 00:00:00

  • Isolation fo 15alpha-hydroxypregnenolone and 15alpha-hydroxydehydroisoandrosterone from human pregnancy urine.

    abstract::15alpha-Hydroxydehydroisoandrosterone and 15alpha-hydroxypregnenolone were isolated from hydrolyzed extracts of human late pregnancy urine and identified by means of the isotope dilution technique. In two separate determinations the excretion rate of 15alpha-hydroxydehydroisoandrosterone was found to be 1.7 and 3.2 mi...


    pub_type: 杂志文章


    authors: Stanczyk FZ,Stern M,Solomon S

    更新日期:1978-05-01 00:00:00

  • Binding characteristics of [3H]delta(5)-androstene-3beta,17beta-diol to a nuclear protein in the rabbit vagina.

    abstract::In this study, we investigated the binding characteristics of [3H]Delta(5)-androstene-3beta,17beta-diol to rabbit vaginal cytosolic and nuclear extracts and in freshly excised intact tissue strips. [3H]delta(5)-Androstene-3beta,17beta-diol bound to a protein(s) in the vaginal nuclear extract with high affinity (K(d)=3...


    pub_type: 杂志文章


    authors: Traish AM,Huang YH,Min K,Kim NN,Munarriz R,Goldstein I

    更新日期:2004-01-01 00:00:00

  • Effects of adrenal hormones on the expression of adiponectin and adiponectin receptors in adipose tissue, muscle and liver.

    abstract:BACKGROUND:Adiponectin, an insulin-sensitive hormone that is primarily synthesized in adipose tissue, exerts its effects by binding to two receptors, adipoR1 and adipoR2. Little is known regarding the effects of glucocorticoids on the expression of adiponectin receptors. METHODS:Male Wistar rats were bilaterally adren...


    pub_type: 杂志文章


    authors: de Oliveira C,Iwanaga-Carvalho C,Mota JF,Oyama LM,Ribeiro EB,Oller do Nascimento CM

    更新日期:2011-11-01 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...


    pub_type: 杂志文章


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

    更新日期:2008-03-01 00:00:00

  • Electrical responses to 1alpha,25(OH)2-Vitamin D3 and their physiological significance in osteoblasts.

    abstract::Osteoblasts are a main target for the steroid 1alpha,25(OH)2-Vitamin D3 (1,25D3), where a major outcome is the modulation of the bone remodeling process. 1,25D3 deficiency leads to clinical disorders such as osteomalacia and osteoporosis, characterized by a state of insufficiently calcified tissue and bone loss, respe...


    pub_type: 杂志文章


    authors: Zanello LP,Norman AW

    更新日期:2004-08-01 00:00:00

  • Measurement of cortisol secretion rate by stable isotope methodology following oral administration of 13C-labeled cortisol to a human subject.

    abstract::Plasma concentration measurements of 13C-labeled cortisol ([1,2,4,19-13C(4)]cortisol, cortisol-13C(4)) and its metabolite cortisone-13C(4) were made simultaneously with measurements of endogenous cortisol and cortisone by gas chromatography-mass spectrometry (GC-MS). After administering a small amount (3mg) of cortiso...


    pub_type: 杂志文章


    authors: Kasuya Y,Yokokawa A,Shibasaki H,Furuta T

    更新日期:2002-08-01 00:00:00

  • The measurement of 4-androstene-3, 11, 17-trione (11-oxo-androstenedione) by radioimmunoassay in human plasma.

    abstract::A radioimmunoassay (RIA) method is described for the determination of 4-androstene-3, 11, 17-trione (11-oxo-androstenedione) in human plasma. 4-androstene-3, 11, 17-trione 3-(0-carboxymethyl) oxime-bovine serum albumin conjugate was used to generate highly specific antiserum in rabbits. Cross reactivities of several o...


    pub_type: 杂志文章


    authors: Schlaghecke R,Kley HK,Krüskemper HL

    更新日期:1984-07-01 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...


    pub_type: 杂志文章


    authors: Bukhari AR,Guessab A,Nicol ML

    更新日期:1981-07-01 00:00:00

  • Sterols of the cultured euglenid Eutreptia viridis: a novel delta 23-unsaturated sterol.

    abstract::The sterol mixture isolated from the marine alga Eutreptia viridis consists mainly of delta 5,7-dienes which account for 80% of the free sterols. Eighteen different sterols were detected, including a novel sterol with the rare delta 23-unsaturation, viz. 24-ethylcholesta-5,7,23Z-trien-3 beta-o1. ...


    pub_type: 杂志文章


    authors: Zielinski J,Kokke WC,Fenical W,Djerassi C

    更新日期:1982-10-01 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. ...


    pub_type: 杂志文章


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

    更新日期:2009-09-01 00:00:00

  • Synthesis of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione.

    abstract::The 21-hydroxy analogues of 11,19-oxidoprogesterone and 6,19-oxidoprogesterone have been synthesized from readily available materials. Hydroxylation at C-21 was effected with iodosobenzene (from phenyliodosodiacetate and methanolic potassium hydroxide) on a 20-ketopregnane. For the 11,19-oxido derivative, the hydroxyl...


    pub_type: 杂志文章


    authors: Veleiro AS,Nevado MV,Monteserín MC,Burton G

    更新日期:1995-03-01 00:00:00

  • Solid-phase chemical synthesis and in vitro biological evaluation of novel 2β-piperazino-(20R)-5α-pregnane-3α,20-diol N-derivatives as anti-leukemic agents.

    abstract::The steroid nucleus is an interesting scaffold for the development of new therapeutic agents. Within the goal of identifying anticancer agents, new pregnane derivatives were prepared by using a sequence of liquid and solid-phase reactions. After we dehydrated epi-allopregnanolone in one step with diethylaminosulfur tr...


    pub_type: 杂志文章


    authors: Jegham H,Maltais R,Dufour P,Roy J,Poirier D

    更新日期:2012-11-01 00:00:00

  • The ecdysteroids from the tobacco hornworm during pupal-adult development five days after peak titer of molting hormone activity.

    abstract::Six naturally occurring C27 ecdysteroids were isolated and identified from the tobacco hornworm during pupal-adult development five days after peak titer of molting hormone activity. In order of decreasing quantities the hormones were: 20,26-dihydroxyecdysone, 3-epi-20-hydroxyecdysone, 20hydroxyecdysone, 3-epi-20,26-d...


    pub_type: 杂志文章


    authors: Kaplanis JN,Thompson MJ,Dutky SR,Robbins WE

    更新日期:1979-09-01 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...


    pub_type: 杂志文章


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

    更新日期:1996-07-01 00:00:00

  • Induction of oxiapoptophagy on 158N murine oligodendrocytes treated by 7-ketocholesterol-, 7β-hydroxycholesterol-, or 24(S)-hydroxycholesterol: Protective effects of α-tocopherol and docosahexaenoic acid (DHA; C22:6 n-3).

    abstract::In demyelinating or non-demyelinating neurodegenerative diseases, increased levels of 7-ketocholesterol (7KC), 7β-hydroxycholesterol (7β-OHC) and 24(S)-hydroxycholesterol (24S-OHC) can be observed in brain lesions. In 158N murine oligodendrocytes, 7KC triggers a complex mode of cell death defined as oxiapoptophagy, in...


    pub_type: 杂志文章


    authors: Nury T,Zarrouk A,Mackrill JJ,Samadi M,Durand P,Riedinger JM,Doria M,Vejux A,Limagne E,Delmas D,Prost M,Moreau T,Hammami M,Delage-Mourroux R,O'Brien NM,Lizard G

    更新日期:2015-07-01 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...


    pub_type: 杂志文章


    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

  • Synthesis of a human long-term oxymetholone metabolite.

    abstract::A long-term metabolite of the doping agent oxymetholone (OXM-M2, 17β-hydroxymethyl-2,17α-methyl-18-norandrost-13-en-3-one) which has been identified by GC-MS/MS was synthesized from commercially available materials. Two efficient synthetic routes to access both C-17 epimers of tentative metabolites were developed. The...


    pub_type: 杂志文章


    authors: Kratena N,Biedermann N,Stojanovic B,Göschl L,Weil M,Enev VS,Gmeiner G,Gärtner P

    更新日期:2019-10-01 00:00:00

  • In vivo metabolism of 3H-testosterone in adult male rats: effects of estrogen administration.

    abstract::The metabolism of testosterone (T) was studied in normal adult male rats using a constant infusion of trace amounts of the 3H-steroid into a tail vein for 3 h in order to attain a state of equilibrium. Samples of plasma, liver, kidney, prostate, seminal vesicles and muscle were analysed for 3H-testosterone, 3H-5alpha-...


    pub_type: 杂志文章


    authors: Lee DK,Bird CE,Clark AF

    更新日期:1975-07-01 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...


    pub_type: 杂志文章


    authors: Davies E,Kenyon CJ,Fraser R

    更新日期:1985-06-01 00:00:00

  • Effects of mifepristone on endometrial receptivity.

    abstract::At the development of receptivity the endometrium undergoes specific changes. Several factors have been suggested as markers of endometrial receptivity. A common feature for most of these factors is that they are directly, or indirectly, regulated by progesterone. The effect of various doses and regimens of mifepristo...


    pub_type: 杂志文章,评审


    authors: Danielsson KG,Marions L,Bygdeman M

    更新日期:2003-11-01 00:00:00