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Search for "steroid" in Full Text gives 75 result(s) in Beilstein Journal of Organic Chemistry.

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

  • Lucas Guillemard and
  • Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

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  • synthetically meaningful σ-bromo esters. The mildness of the reaction conditions warranted tolerance of sensitive and/or biologically relevant sugar, menthol, and steroid motifs (Figure 37). The mechanistic studies conducted by Ackermann et al. clearly showed that the metallacyclic intermediates resulting from
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Published 21 Jul 2020

A smart deoxyribozyme-based fluorescent sensor for in vitro detection of androgen receptor mRNA

  • Ekaterina A. Bryushkova,
  • Erik R. Gandalipov and
  • Julia V. Nuzhina

Beilstein J. Org. Chem. 2020, 16, 1135–1141, doi:10.3762/bjoc.16.100

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  • -based fluorescent sensor (SDFS), designed for the quick and efficient verification of human androgen receptor (AR) mRNA. The AR (alternative name NR3C4) belongs to the steroid nuclear receptor superfamily, capable of being activated after a direct interaction with nuclear DNA and works as a
  • samples. As a negative control samples containing total RNA from HeLa cells, which referred to be steroid receptor negative [27], with SDFS and malachite green dye were incubated and measured as well (Figure 3). A comparison of the fluorescence data presented above showed that the signal from samples
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Published 27 May 2020

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

  • Rodrigo Costa e Silva,
  • Luely Oliveira da Silva,
  • Aloisio de Andrade Bartolomeu,
  • Timothy John Brocksom and
  • Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

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  • -rich and electron-deficient groups in the arylsulfinic acid and alkyl sulfinates, such as sodium ethylsulfinate and sodium methylsulfinate (Scheme 19). The authors also showed that the methodology can be applied to the sulfonation of steroid drug arimistane in 45% yield (Scheme 20). The mechanistic
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Published 06 May 2020

Diversity-oriented synthesis of 17-spirosteroids

  • Benjamin Laroche,
  • Thomas Bouvarel,
  • Martin Louis-Sylvestre and
  • Bastien Nay

Beilstein J. Org. Chem. 2020, 16, 880–887, doi:10.3762/bjoc.16.79

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  • diversity-oriented approaches were developed, generating diversity either at the construction stage (Scheme 1a) [34][35], or by transformation of the main steroidal core (Scheme 1b) [36][37][38][39]. An important class of steroid medicines, also bearing a crucial propargylic alcohol function for our
  • transcription, or directly bind nuclear receptors [59][60][61]. In principle, steroids could thus be used as cargo molecules to deliver new chemical entities inside the nucleus, highlighting the potential of hybrid steroid molecules [62]. For example, De Riccardis designed steroid scaffolds directly fused to a
  • [65]. Today, the research on steroids is still extremely active thanks to their huge medicinal potential [66][67]. In this context and owing to the commercial availability of 17-ethynyl-17-hydroxysteroids, we decided to apply a DOS approach to the synthesis of steroid analogues based on mestranol (1
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Published 28 Apr 2020

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

  • Valerian Dragutan,
  • Ileana Dragutan,
  • Albert Demonceau and
  • Lionel Delaude

Beilstein J. Org. Chem. 2020, 16, 738–755, doi:10.3762/bjoc.16.68

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  • subunit, including Diels–Alder cycloaddition and advanced functionalization reactions, gave access to manzamine A and E. Rhodexin A Jung et al. [87][88][89] succeeded in the stereoselective synthesis of rhodexin A (17), a steroid with potent cardiotonic properties and with activity against human leukemia
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Published 16 Apr 2020

Recent advances in photocatalyzed reactions using well-defined copper(I) complexes

  • Mingbing Zhong,
  • Xavier Pannecoucke,
  • Philippe Jubault and
  • Thomas Poisson

Beilstein J. Org. Chem. 2020, 16, 451–481, doi:10.3762/bjoc.16.42

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  • yield, with an excellent functional group tolerance. Moreover, a complex steroid derivative was efficiently reduced under the standard conditions. Activated aryl bromides were also readily reduced under similar conditions, even if they were tedious electron-rich aryl bromide substrates, giving low yield
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Published 23 Mar 2020

Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

  • Eric J. N. Helfrich,
  • Geng-Min Lin,
  • Christopher A. Voigt and
  • Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

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  • functional roles, which range from widely distributed metabolites like cholesterol, to those with more restricted distribution like vitamins A and D, carotenoids, and steroid hormones, to some with highly restricted distribution like pheromones, fragrances, and defense metabolites [2][3]. Many of the more
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Published 29 Nov 2019

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

  • Xiaowei Li,
  • Xiaolin Shi,
  • Xiangqian Li and
  • Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

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  • hydrocarbons, substituted cyclic molecules, terpenoids, and steroid derivatives, were selectively fluorinated at some otherwise inaccessible sites, however, in low to moderate yields. On the other hand, the same group [83] developed Mn(salen)Cl as a catalyst for the direct C–H fluorination at benzylic
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Published 23 Sep 2019

1,2,3-Triazolium macrocycles in supramolecular chemistry

  • Mastaneh Safarnejad Shad,
  • Pulikkal Veettil Santhini and
  • Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

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  • macrocycles are a class of steroid-based receptors which can host polar molecules in nonpolar solvents because of their amphiphilic nature. As a result, their design and synthesis has been a topic of substantial research interest in supramolecular chemistry [32][33]. Various synthetic methods have been
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Published 12 Sep 2019

Steroid diversification by multicomponent reactions

  • Leslie Reguera,
  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

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  • materials for relevant MCRs such as those based on imine and isocyanide. The focus is mainly posed on proving the amenability of MCRs for the diversity-oriented derivatization of naturally occurring steroids and the construction of complex steroid-based platforms for drug discovery, chemical biology and
  • steroid biological functions. Such oxygenated and alkene groups represent the entrance door for subsequent synthetic modifications, including the incorporation of MCR reactive functionalities. In the last two decades, MCRs have emerged as effective tools for the rapid derivatization of steroidal skeletons
  • with steroids. Herein, we provide a comprehensive review describing – to our understanding – the most important inputs of the utilization of MCRs in the structural diversification of steroids. The review is divided in different aspects of steroid chemistry, such as modification of the side chain and
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Published 06 Jun 2019

Synthesis of (macro)heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions

  • Angélica de Fátima S. Barreto and
  • Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2019, 15, 906–930, doi:10.3762/bjoc.15.88

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  • chimeric peptoid macrocycles containing steroid moieties [37]. The process was based on designing a 4-fold Ugi-4CR macrocyclization by using the steroidal diisocyanide 107 with diacid 108 or diamine 109 (Scheme 21). According to the authors, this was the first report of repetitive multicomponent reactions
  • approach provided the synthesis of steroid-biaryl ether hybrid macrocycles 117 and 118 with up to 68 members by the MiBs strategy. Another representative example of MiBs is the synthesis of the biaryl ether-containing macrocycles 123a–f (Scheme 23) [39]. The synthetic strategy involved the mixing of three
  • [41] performed the first use of the diamine/diacid combination of bidirectional Ugi-MiBs in the synthesis of novel steroid–peptoid hybrid macrocycles. Scheme 25 shows two examples using this combination for the synthesis of cholane–peptoid hybrid macrocycles. Another application of the MiBs approach
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Published 15 Apr 2019

Application of olefin metathesis in the synthesis of functionalized polyhedral oligomeric silsesquioxanes (POSS) and POSS-containing polymeric materials

  • Patrycja Żak and
  • Cezary Pietraszuk

Beilstein J. Org. Chem. 2019, 15, 310–332, doi:10.3762/bjoc.15.28

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  • research, active in preliminary tests and commercially available second generation Grubbs–Hoveyda catalyst Ru-3 and its nitro derivative Ru-4 were selected. The same authors were able to successfully functionalize allylsilsesquioxane with more challenging, three different steroid derivatives. The reactions
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Published 04 Feb 2019

Degenerative xanthate transfer to olefins under visible-light photocatalysis

  • Atsushi Kaga,
  • Xiangyang Wu,
  • Joel Yi Jie Lim,
  • Hirohito Hayashi,
  • Yunpeng Lu,
  • Edwin K. L. Yeow and
  • Shunsuke Chiba

Beilstein J. Org. Chem. 2018, 14, 3047–3058, doi:10.3762/bjoc.14.283

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  • functionalized cyclopentane 3an and pyrrolidine 3ao, respectively, via 5-exo-trig radical cyclization (Table 2, entries 13 and 14). The present method was capable in functionalizing olefins 2p and 2q installed on steroid scaffolds with high efficiency (Table 2, entries 15 and 16). We next examined the reactions
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Published 13 Dec 2018

Pd-Catalyzed microwave-assisted synthesis of phosphonated 13α-estrones as potential OATP2B1, 17β-HSD1 and/or STS inhibitors

  • Rebeka Jójárt,
  • Szabolcs Pécsy,
  • György Keglevich,
  • Mihály Szécsi,
  • Réka Rigó,
  • Csilla Özvegy-Laczka,
  • Gábor Kecskeméti and
  • Erzsébet Mernyák

Beilstein J. Org. Chem. 2018, 14, 2838–2845, doi:10.3762/bjoc.14.262

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  • -benzyl ether function displayed substantial submicromolar OATP2B1 inhibitory activity. The inhibitory effects of the compounds on human placental steroid sulfatase (STS) and 17β-hydroxysteroid dehydrogenase type 1 isozyme (17β-HSD1) were investigated by in vitro radiosubstrate incubation methods. None of
  • large circulatory reservoir catalyzed by steroid sulfatase (STS), is one of the major alternative sources of prehormone estrone for the local supply of estrogens [2]. The availability of free estrone on the cellular level depends on the expression of STS and/or SULT, which catalyze the sulfation of the
  • reduction of the 17-oxo function leading to 17β-estradiol. This last step of the estrogen biosynthesis is catalyzed by the 17β-hydroxy steroid dehydrogenase type 1 isoenzyme (17β-HSD1) [13]. Thus STS and 17β-HSD1 became important drug targets in estrogen-dependent diseases [1][14]. Their inhibition could be
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Published 14 Nov 2018

The first Pd-catalyzed Buchwald–Hartwig aminations at C-2 or C-4 in the estrone series

  • Ildikó Bacsa,
  • Dávid Szemerédi,
  • János Wölfling,
  • Gyula Schneider,
  • Lilla Fekete and
  • Erzsébet Mernyák

Beilstein J. Org. Chem. 2018, 14, 998–1003, doi:10.3762/bjoc.14.85

Graphical Abstract
  • -natural C-18 steroid containing cis junction of rings C and D [21][22]. This core-modified compound differs from its natural 13β counterpart not only in the configuration of C-13, but also its more flexible conformation. Poirier et al. investigated the in vitro and in vivo estrogenic activity of 3,17
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Published 04 May 2018

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

  • Eirinaios I. Vrettos,
  • Gábor Mező and
  • Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

Graphical Abstract
  • , present on the cell surface of the targeted tissues and not within their cytosol or nucleus (i.e., steroid receptors [33]). The selected receptor should be uniquely expressed or overexpressed on cancer cells (usually 3-fold or higher in comparison with normal cells). Additionally, it should be expressed
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Published 26 Apr 2018

Crystal structure of the inclusion complex of cholesterol in β-cyclodextrin and molecular dynamics studies

  • Elias Christoforides,
  • Andreas Papaioannou and
  • Kostas Bethanis

Beilstein J. Org. Chem. 2018, 14, 838–848, doi:10.3762/bjoc.14.69

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  • inclusion compound remains very stable in aqueous solution at both temperatures. Keywords: beta-cyclodextrin; cholesterol; crystal structure; molecular dynamics; Introduction Cholesterol ((3β)-cholest-5-en-3-ol, CHL, Figure 1a) is a polycyclic steroid that is synthesized in mammalian cells and has a
  • significant role in biology as an essential structural component of the cell walls and as precursor for the biosynthesis of several substances such as vitamin D, bile acids and steroid hormones. However, the consumption of food rich in cholesterol like meat, eggs and dairy products has been associated with
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Published 11 Apr 2018

Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review

  • Fabio Tonin and
  • Isabel W. C. E. Arends

Beilstein J. Org. Chem. 2018, 14, 470–483, doi:10.3762/bjoc.14.33

Graphical Abstract
  • reduction) and the specific hydroxylation and dehydroxylation of suitable positions in the steroid rings. In this minireview, we critically analyze the state of the art of the production of UDCA by several chemical, chemoenzymatic and enzymatic routes reported, highlighting the bottlenecks of each
  • secondary bile acid. It is produced by bacteria in the colon from CDCA trough the dehydroxylation of the C7 functional group of the steroid framework. Low percentages of other secondary bile acids and related keto derivatives can be found in the bile. The solubility properties, interactions and metabolisms
  • are related to the position and stereochemistry of the hydroxy groups attached to the steroid ring. A general structure with the names of several bile acids is reported in Figure 2. Deconjugation Free bile acids can be obtained from the corresponding bile amides (with glycine and taurine) through a
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Published 20 Feb 2018

Synthesis of ergostane-type brassinosteroids with modifications in ring A

  • Vladimir N. Zhabinskii,
  • Darya A. Osiyuk,
  • Yuri V. Ermolovich,
  • Natalia M. Chaschina,
  • Tatsiana S. Dalidovich,
  • Miroslav Strnad and
  • Vladimir A. Khripach

Beilstein J. Org. Chem. 2017, 13, 2326–2331, doi:10.3762/bjoc.13.229

Graphical Abstract
  • ; metabolites; Introduction The group of steroid plant hormones called brassinosteroids (BS) currently comprises about 70 compounds [1]. It is generally accepted that only few of them (such as brassinolide, castasterone, epibrassinolide, etc.), possessing 2α,3α-, (22R,23R)-diol groups, B-lactone, and 6-ketone
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Published 02 Nov 2017

Diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside: synthesis, derivatives and antimicrobial activity

  • Henryk Myszka,
  • Patrycja Sokołowska,
  • Agnieszka Cieślińska,
  • Andrzej Nowacki,
  • Maciej Jaśkiewicz,
  • Wojciech Kamysz and
  • Beata Liberek

Beilstein J. Org. Chem. 2017, 13, 2310–2315, doi:10.3762/bjoc.13.227

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  • the obtained compounds are active against Gram-positive bacteria and Candida type fungi. Keywords: antimicrobial activities; D-galactosamine; diosgenin; glycosylation; saponin; tetrachlorophthalimido derivatives; Introduction Saponins are steroid or triterpenoid glycosides found in various plants [1
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Published 01 Nov 2017

Conjugated nitrosoalkenes as Michael acceptors in carbon–carbon bond forming reactions: a review and perspective

  • Yaroslav D. Boyko,
  • Valentin S. Dorokhov,
  • Alexey Yu. Sukhorukov and
  • Sema L. Ioffe

Beilstein J. Org. Chem. 2017, 13, 2214–2234, doi:10.3762/bjoc.13.220

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  • exploited the Michael addition of enolates to nitrosoalkenes in their studies towards syntheses of 3-methoxy-9β-estra(1,3,5(10))trien(11,17)dione (25) (1977) [31] and (+/−)-isocomene (1981) [32]. The key carbon–carbon bond formation step in the synthesis of steroid 25 was the stereoselective reaction of α
  • hydrolysis of the oximino group gave target steroid 25 with the desired configuration of all stereogenic centers. In the attempted route to (+/−)-isocomene, Oppolzer and co-workers suggested pentalenone 29, accessible by an intramolecular aldol condensation/elimination of diketone 30, as a key precursor
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Published 23 Oct 2017

Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly

  • Weizhun Yang,
  • Bo Yang,
  • Sherif Ramadan and
  • Xuefei Huang

Beilstein J. Org. Chem. 2017, 13, 2094–2114, doi:10.3762/bjoc.13.207

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  • utilized glycosyl sulfoxide donors for glycosylation of unreactive substrates such as steroid derivative 2 by the Kahne group [25]. The axial C-7 hydroxy group in 2 is sterically hindered due to unfavorable 1,3-diaxial interactions. The traditional premixed glycosylation gave only low yields (<30%) of the
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Published 09 Oct 2017

Accessing simply-substituted 4-hydroxytetrahydroisoquinolines via Pomeranz–Fritsch–Bobbitt reaction with non-activated and moderately-activated systems

  • Marco Mottinelli,
  • Mathew P. Leese and
  • Barry V. L. Potter

Beilstein J. Org. Chem. 2017, 13, 1871–1878, doi:10.3762/bjoc.13.182

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  • electrophilic aromatic substitution that is strongly impacted by the effects of the substituents on the electron density of the aromatic ring in intermediate 4. Given our established interest in exploring structural mimetics for the steroid nucleus we were drawn to explore whether the PFB reaction could be used
  • to access libraries of regioisomeric N-aryl-1,2,3,4-tetrahydroisoquinoline derivatives that might facilitate the design of new structural templates for steroid-binding receptors. We thus evaluated the robustness and flexibility of this approach to the THIQ system and considered, in particular, the
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Published 06 Sep 2017

Strategies toward protecting group-free glycosylation through selective activation of the anomeric center

  • A. Michael Downey and
  • Michal Hocek

Beilstein J. Org. Chem. 2017, 13, 1239–1279, doi:10.3762/bjoc.13.123

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  • worked well with not only simple aliphatic and phenolic alcohols but also with amino acids and steroid alcohols (Figure 1). The authors posit that the stereoselectivity can be rationalized by an oxycarbenium/BF3-coordinated 3-bromo-2-pyridyloxy ion-pair intermediate that is displaced by the alcohol in an
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Published 27 Jun 2017

Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands

  • Nikolay V. Lukashev,
  • Gennadii A. Grabovyi,
  • Dmitry A. Erzunov,
  • Alexey V. Kazantsev,
  • Gennadij V. Latyshev,
  • Alexei D. Averin and
  • Irina P. Beletskaya.

Beilstein J. Org. Chem. 2017, 13, 564–570, doi:10.3762/bjoc.13.55

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  • arylaminocholanes and cholane-diaminoanthraquinone derivatives by Pd- and Cu-catalyzed amination. Such compounds not only have cation binding properties, but also might be easily introduced in lipid membranes to form ion channels. Appropriate close location of lipophilic steroid fragments in bis(cholanediamino
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Published 20 Mar 2017
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