42979-83-9

Upstream product

• 53-16-7 Estrone 

Downstream Products

• 20823-11-4 2,4-dinitro-17β-estradiol 

Relevant academic research and scientific papers

New estrone oxime derivatives: Synthesis, cytotoxic evaluation and docking studies

The interest in the introduction of the oxime group in molecules aiming to improve their biological effects is increasing. This work aimed to develop new steroidal oximes of the estrane series with potential antitumor interest. For this, several oximes were synthesized by reaction of hydroxylamine with the 17-ketone of estrone derivatives. Then, their cytotoxicity was evaluated in six cell lines. An estrogenicity assay, a cell cycle distribution analysis and a fluorescence microscopy study with Hoechst 3358 staining were performed with the most promising compound. In addition, molecular docking studies against estrogen receptor α, steroid sulfatase, 17β-hydroxysteroid dehy-drogenase type 1 and β-tubulin were also accomplished. The 2-nitroestrone oxime showed higher cytotoxicity than the parent compound on MCF-7 cancer cells. Furthermore, the oximes bearing halogen groups in A-ring evidenced selectivity for HepaRG cells. Remarkably, the ?9,11-estrone oxime was the most cytotoxic and arrested LNCaP cells in the G2 /M phase. Fluorescence microscopy studies showed the presence of condensed DNA typical of prophase and condensed and fragmented nuclei characteristic of apoptosis. However, this oxime promoted the proliferation of T47-D cells. Interestingly, molecular docking studies estimated a strong interaction between ?9,11-estrone oxime and estrogen receptor α and β-tubulin, which may account for the described effects.

Novel nitration of estrone by metal nitrates

Nitration of estrone has been investigated with different types of metal salts in the presence of solid surfaces under various conditions.

New selenosteroids as antiproliferative agents

Starting from natural steroids (diosgenin, hecogenin, smilagenin, estrone), we have prepared a wide panel of selenoderivatives, including benzoselenazolones, selenosemicarbazones, isoselenocyanates, selenoureas, selenocyanates and diselenides, with the aim of developing new families of potential chemotherapeutic agents. The modification of the organoselenium moieties, and their position on the steroid provided valuable information concerning the antiproliferative activities. Among all the families accessed herein, the best profile was achieved for selenoureas on the A ring of estrone, which exhibited GI50 values in the range 2.0-4.1 μM for all the tested tumor cell lines, with increased potency compared with commonly used chemotherapeutic agents, like 5-fluorouracil and cisplatin. Cell cycle analysis revealed that selenoureas induced accumulation of cells in the G1 phase of the cell cycle in the breast cancer cell lines HBL-100 and T-47D; therefore, a different mechanism than cisplatin, that induces cell cycle accumulation in the S phase as a result of DNA damage, must be involved. In the rest of the tumor cells, a slight increase of the S compartment was observed. Moreover, selenosteoids turned out to be excellent glutathione peroxidase (GPx) mimics for the catalytic removal of deleterious H2O2 (t1/2 8.0-22.5 min) and alkyl peroxides (t1/2 23.0-38.9 min) when used in substoichiometric amounts (1% molar ratio), thus providing a valuable tool for reducing the intrinsic oxidative stress in tumor progression.

Surface-mediated highly efficient regioselective nitration of aromatic compounds by bismuth nitrate

Montmorillonite impregnated with bismuth nitrate was found to be an excellent reagent for aromatic nitration in high yield. (C) 2000 Elsevier Science Ltd.

The behaviour of some estrogens in the nitration process II. A comparative study of 18-crown-6 ether effect on estrone nitration with NO2, NO+2, HNO2 and NO-2 species

The estrone 1 conversion by nitration and the percentage of nitroderivatives obtained, i.e. 2-nitroestrone 2, 4-nitroestrone 3 and 2,4-dinitroestrone 4, depend on the nitration procedure used (through NO+2, HNO2, NO2 gas or NO-2 anion in the presence of crown ether 18C6, respectively). The dinitroderivative 4 was obtained only in the nitration process by means of NO2 gas. Estrone 1 was also nitrated with NO-2 anion in the presence of valinomycin antibiotic macrocyclic ionophore; the procedure was identical to that adopted for 18C6.