Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction

• Thomas Brandt,
• Pascal Lentes,
• Jeremy Rudtke,
• Michael Hösgen,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36

• tetracyclic steroid scaffolds such as 17β-estradiol [18], where the diazocine core mimics the framework of the bioactive compound (Figure 1a). The other option is to attach the diazocine photoswitch as a substituent (appendix) to the biologically active molecule (Figure 1b) [6][10][19][20][21]. The art of

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• most common applications being the treatment of breast cancer. Studies have shown that breast cancer is tied to the ratio of 16α-hydroxyestrone (16αOHE1) and 2-hydroxyestrone (2OHE1), which are products of the metabolism of the estrogen 17β-estradiol. BIMs can shift the process of estrogen metabolism

Cyclodextrins as building blocks for new materials

• Miriana Kfoury and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2023, 19, 889–891, doi:10.3762/bjoc.19.66

• intravenous voriconazole antimycotic, and randomly methylated β-CD in a nasal spray for hormone replacement therapy with 17β-estradiol. Yet, the current interest goes far beyond the simple use of CDs as a delivery system for therapeutic agents. Current research interests focus on the intrinsic activity of CDs

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

• Alexios I. Vicatos,
• Zakiena Hoossen and
• Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

• ingredients (APIs) is necessary to render them bioavailable. This study addresses the poor solubility of two potent steroid hormones, 17β-estradiol (BES) and progesterone (PRO), via their complexation with two water-soluble native cyclodextrins (CDs) namely β-CD and γ-CD. The hydrated inclusion complexes β

• : cyclodextrin; complexation; 17β-estradiol; progesterone; solubility; X-ray diffraction; Introduction The insolubility of active pharmaceutical ingredients (APIs) and other bioactive compounds in aqueous media and the associated challenges for effective drug delivery are well known to have beleaguered the

• their chemical instability, adverse side effects such as gastrointestinal irritation, and unpleasant tastes and odours [1][2][3][4][5]. Here we report an investigation of the cyclodextrin (CD) inclusion of two notable bioactive compounds (Figure 1), namely the most potent human estrogen, 17β-estradiol

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

• 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

• transformed in order to get 2-substituted derivatives [21][22][23]. On the basis of the crystal structure of 17β-HSD1 in its complex with 17β-estradiol, Möller et al. described, that there is an unoccupied lipophilic tunnel located near the C-2 atom of the steroid [24]. Their strategy for improving the

• introduction of a large diphenylphosphine oxide moiety onto C-2 improves the binding of the steroid to the enzyme. C-4-substituted 3-OH derivatives 12a and 12b barely suppressed the estrone to 17β-estradiol conversion. The same tendency showed up in our previous works regarding the inhibitory potentials of

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

• estrogen receptors (ERα and ERβ) [28]. Certain derivatives of 2- or 4-aminoestrone or their 3-methyl ether possess diverse biological activities, including enzyme inhibitory or antiproliferative properties [1][2][3][29][30]. The 17β-HSD1 enzyme is responsible for the reduction of estrone into 17β-estradiol

Synthesis of novel 13α-estrone derivatives by Sonogashira coupling as potential 17β-HSD1 inhibitors

• Ildikó Bacsa,
• Rebeka Jójárt,
• János Wölfling,
• Gyula Schneider,
• Bianka Edina Herman,
• Mihály Szécsi and
• Erzsébet Mernyák

Beilstein J. Org. Chem. 2017, 13, 1303–1309, doi:10.3762/bjoc.13.126

• compounds 13α-estrone or 13α-estrone 3-methyl ether [13]. The 17β-HSD1 enzyme is responsible for the stereospecific reduction of prehormone estrone into the main estrogenic hormone 17β-estradiol [14][15]. 17β-Estradiol may enhance the proliferation of certain cancer cells [16]. The inhibition of 17β-HSD1

• and 11, nevertheless, exert weak inhibitions on the estrone to 17β-estradiol conversion The results reveal a great influence of the 2,4-regioisomerism on the inhibition potential of the iodinated 3-methyl ethers 4 and 6, the phenylalkynyl 8 and 10 and the phenylalkyl 16 and 18 3-hydroxy compounds

Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

• Mino R. Caira,
• Susan A. Bourne,
• Halima Samsodien and
• Vincent J. Smith

Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281

• endogenous metabolite of the most common estrogen hormone, 17β-estradiol, has been intensively studied owing to its proven potent antiangiogenic, antiproliferative and antitumoral activities [2][3]. However, its poor bioavailability has retarded its development as a drug [4][5]. Although recent reports of

• minor to a host glycosidic oxygen atom. The results presented here are of general interest in the context of CD–steroid interaction, with special reference to estranes that contain a 17-OH function (e.g., the estrogen sex hormone 17β-estradiol). Previous studies of the anticancer activities of 2ME have

• generously provided by Shimoda Biotech (Pty) Ltd (Port Elizabeth, South Africa). Synthesis of the sample of 2ME from commercially available 17β-estradiol was reported earlier [9]. The following cyclodextrins (CDs) were purchased from Cyclolab (Budapest, Hungary) and were used as received: α-CD, β-CD, γ-CD