Abstract:
:Synthetic transformations of steroids for drug discovery and improvement of drug effectiveness have been an important part of modern medicinal chemistry and pharmaceutical sciences. Pentacyclic triterpenoids, being represented in the nature by various structures and biogenetically related to steroids, can largely expand the spectrum of biologically active steroidal agents via synthesis of the so-called "triterpenoid-steroid" hybrids. In the presented work, the nitrile anion cyclizations of 3,4-secolupane and 3,4-seco-oleanane nitriles and follow-up synthetic transformations of the cyclized products with formation of the gemm-dimethyl-free A ring "triterpenoid-steroid" hybrids were studied. Furthermore, the resulting cyclic compounds were modified at C3, C4, and/or C5 positions of ring A, as well as at C20, C28, and C30 positions of the isopropylidene moiety in the case of lupane triterpenoids. The cytotoxic effect of the synthesized compounds against seven cancer cell lines HEp-2, HCT 116, MS, RD TE32, A549, MCF7, and PC3 was evaluated. The in silico identification of potential anticancer protein targets with regard to the compounds, which were active at micromolar concentrations against tested cell lines, was carried out. The molecular docking studies showed that compound 19, which demonstrated most pronounced cytotoxicity (IC50 0.64-3.17 μM) against all tested cell lines, fits well the active sites of CDK6 and HER2/neu.
journal_name
Steroidsjournal_title
Steroidsauthors
Tolmacheva IA,Nazarov AV,Eroshenko DV,Grishko VVdoi
10.1016/j.steroids.2018.10.005subject
Has Abstractpub_date
2018-12-01 00:00:00pages
131-143eissn
0039-128Xissn
1878-5867pii
S0039-128X(18)30192-2journal_volume
140pub_type
杂志文章相关文献
STEROIDS文献大全abstract::Corticosteroids were used normally as anti-inflammatory drugs. However, in some area certain corticosteroids might be illegally used as growth promoting agent in feed, and as prohibited doping substances in game and sport for human or/and animal performance-enhancing. Synthesized structural similar corticosteroids wer...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/j.steroids.2020.108739
更新日期:2021-01-01 00:00:00
abstract::Incubation of aldosterone with confluent layers of A6 (toad kidney) cells leads to its hydroxylation at the 6 beta-position. 6 beta-Hydroxyaldosterone is the major metabolite when the incubation is carried out at pH 6.8, whereas the product comprises 6 beta-hydroxy-17-isoaldosterone accompanied by some 6 beta-hydroxya...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/0039-128x(90)90084-o
更新日期:1990-11-01 00:00:00
abstract::The properties of 5-ene-3 beta hydroxysteroid oxidoreductase (3 beta-HSD) from human placental homogenates were studied in vitro. The apparent Michaelis constants for 3 beta-HSD with the substrates pregnenolone (delta 5P) and dehydroepiandrosterone (DHA) were 170 nM and nM respectively. The optimal pH for both these s...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/s0039-128x(79)80002-1
更新日期:1979-01-01 00:00:00
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...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/j.steroids.2003.10.006
更新日期:2004-01-01 00:00:00
abstract::A partial synthesis of the title compound, 4'-(dimethylamino)-17 beta-hydroxy-17 alpha-(1-propynyl)benzo[12,12a]-11 alpha,18-cyclo-12a,12b- dihomo-13 alpha-estr-4-en-3-one 1, is reported. The key step in this synthesis represents an intramolecular alkenylaryl radical cyclization. Treatment of 18-[bromo-5-(dimethylamin...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/0039-128x(94)90026-4
更新日期:1994-03-01 00:00:00
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
更新日期:1996-09-01 00:00:00
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
更新日期:1990-10-01 00:00:00
abstract::Counterfeiting and adulteration of pharmaceuticals is a prevalent problem worldwide and represents a major health risk to the population, with anabolic steroids being one of the main classes of drugs consumed and obtained from dubious sources. In this work, we propose the use of the 1H NMR technique to evaluate formul...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/j.steroids.2018.07.002
更新日期:2018-10-01 00:00:00
abstract::Smith-Lemli-Opitz syndrome (SLOS) is caused by deficiency in the terminal step of cholesterol biosynthesis, which is catalyzed by 7-dehydrocholesterol reductase (DHCR7). The disorder exhibits several phenotypic traits including dysmorphia and mental retardation with a broad range of severity. Pathogenesis of SLOS is c...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/j.steroids.2007.07.002
更新日期:2007-10-01 00:00:00
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
更新日期:1996-08-01 00:00:00
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
更新日期:1980-05-01 00:00:00
abstract::While the neuroprotective benefits of estrogen and progesterone in critical illness are well established, the data regarding the effects of androgens are conflicting. Surgical repair of congenital heart disease is associated with significant morbidity and mortality, but there are scant data regarding the postoperative...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/j.steroids.2013.11.003
更新日期:2014-03-01 00:00:00
abstract:BACKGROUND:Congenital adrenal hyperplasia (CAH) caused by 21-hydroxylase deficiency (21OHD) is an autosomal recessive disorder due to mutation in the CYP21A2 gene. OBJECTIVE:To elucidate the genetic basis of 21-hydroxylase-deficient CAH in Hong Kong Chinese patients. PATIENTS AND METHODS:Mutational analysis of the CY...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/j.steroids.2011.04.010
更新日期:2011-09-01 00:00:00
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
更新日期:2010-08-01 00:00:00
abstract::Biotransformation of danazol (1) (17β-hydroxy-17α-pregna-2,4-dien-20-yno-[2,3-d]-isoxazole) with Cunninghamella blakesleeana yielded three new metabolites 2-4 and a known metabolite 5. These metabolites were identified as 14β,17β-dihydroxy-2-(hydroxymethyl)-17α-pregn-4-en-20-yn-3-one (2), 1α,17β-dihydroxy-17α-pregna-2...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/j.steroids.2015.11.010
更新日期:2016-01-01 00:00:00
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
更新日期:1979-01-01 00:00:00
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
更新日期:1992-07-01 00:00:00
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
更新日期:2017-10-01 00:00:00
abstract::Optimal assay conditions for cholesterol 7 alpha-hydroxylase activity in swine liver microsomes were determined. The enzyme activity is induced three-fold by feeding cholestyramine to the swine. This suggests that cholesterol 7 alpha-hydroxylase is likely to be the rate-limiting enzyme for biosynthesis of bile acids i...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/0039-128x(79)90008-4
更新日期:1979-03-01 00:00:00
abstract::Using pregnenolone as a starting material, some 3-substituted 17-[1',2',3']-selenadiazolylpregnenolone derivatives were synthesized, and their structures were characterized by IR, NMR and HRMS. The in vitro antitumor activity of the compounds was assayed against PC-3、SKOV3、T47D、MCF-7 and HEK293T cell lines. The result...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/j.steroids.2018.10.004
更新日期:2018-12-01 00:00:00
abstract::Trimegestone (TMG) is a novel 19-norpregnane progestin under development for hormone replacement therapy and oral contraception. The objective of the current study was to characterize the potency and steroid receptor selectivity of TMG in several in vitro assays and to compare its activity to that of medroxyprogestero...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/s0039-128x(00)00120-3
更新日期:2000-10-01 00:00:00
abstract::A new technique that permits measurement of Androgen-Binding Protein (ABP) is validated by reproducibility, linearity and correlation studies. Using this apparatus allowing Scatchard plot analysis, it is also possible to measure association and dissociation rate constants. In addition, it is a very useful tool for a r...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/0039-128x(88)90174-2
更新日期:1988-10-01 00:00:00
abstract::The nature of the water-soluble products formed by incubating labelled estradiol with uterine peroxidase in the presence of H2O2 and tyrosine was examined by two-dimensional thin-layer chromatography and high voltage electrophoresis. It was shown that the steroid and amino acid were associated in a 1:2 or 1:3 ratio an...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/0039-128x(77)90072-1
更新日期:1977-04-01 00:00:00
abstract::The mass spectral elimination of water in epimeric 1,3-diols of vitamin D3 (colecalciferol) series has been investigated. It was found that the mass spectra of these steroisomers differ sharply in the relative intensities of the ions M-H2O (m/e 382) and a-H2O (m/e +/- 34), where ion a (formed via formal cleavage of th...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/0039-128x(79)90039-4
更新日期:1979-05-01 00:00:00
abstract::In an endeavour to develop potent anti-tumor agents from diosgenin, a series of C-6 derived 1,2,3-triazolyl derivatives were designed and synthesized by employing Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition reaction of novel azides - (22R,25R)-6β-azidospirostan-3β,5α-diol and 6β-azido-7α-hydroxyspirosta-1,4-dien...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/j.steroids.2019.108460
更新日期:2019-11-01 00:00:00
abstract::The synthesis of 16 alpha-3H androgens and estrogens is described. 1-(3H)-Acetic acid in the presence of zinc dust reacts with 16 alpha-bromo-17-ketosteroids to produce 16 alpha-3H-17-ketosteroids. This chemical reaction was used to prepare 16 alpha-3H-dehydroepiandrosterone (I) and 16 alpha-3H-estrone acetate (XI) fr...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/s0039-128x(81)80016-5
更新日期:1981-02-01 00:00:00
abstract:BACKGROUND:Chronic administration of exogenous glucocorticoids is often required in experimental research. We compared the efficacy and reliability of three different methods of continuous glucocorticoid administration in mice. MATERIALS AND METHODS:Male CD1 Swiss White mice aged 7-9 weeks received corticosterone (CS)...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/j.steroids.2008.11.009
更新日期:2009-02-01 00:00:00
abstract::From the fruiting bodies of Ascomycetes Tuber indicum, a new steroidal glucoside with polyhydroxy ergosterol nucleus, tuberoside (2), has been isolated along with additional four known ergosterol derivatives, (22E, 24R)-ergosta-7, 22-dien-3beta, 5alpha, 6beta-triol (1), 5alpha, 8alpha-epidioxy-(22E, 24R)-ergosta-6, 22...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/s0039-128x(01)00105-2
更新日期:2001-10-01 00:00:00
abstract::The biotransformation of a series of delta 4-3-ketosteroids by the fungus Penicillium decumbens ATCC 10436 has been investigated. Conversion to the 5 alpha-dihydrosteroid was observed for several substrates of the androstene and pregnene series: the reaction is tolerant of non-polar substituents (Cl and CH3) at C-4 of...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/0039-128x(94)90020-5
更新日期:1994-11-01 00:00:00
abstract::Estradiol (E2) and other steroids have recently been shown to initiate various intracellular signaling cascades from the plasma membrane, including those stimulating mitogen-activated protein kinases (MAPKs), and particularly extracellular-regulated kinases (ERKs). In this study we demonstrated the ability of E2 to ac...
journal_title:Steroids
pub_type: 杂志文章
doi:10.1016/j.steroids.2003.12.003
更新日期:2004-03-01 00:00:00