60788-62-7Relevant articles and documents
Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C3-Synthons
Wienhold, Max,Molloy, John J.,Daniliuc, Constantin G.,Gilmour, Ryan
supporting information, p. 685 - 689 (2020/11/30)
Modular β-borylacrylates have been validated as programmable, ambiphilic C3-synthons in the cascade annulation of 2-halo-phenol derivatives to generate structurally and electronically diverse coumarins. Key to this [3+3] disconnection is the BPin unit which serves a dual purpose as both a traceless linker for C(sp2)–C(sp2) coupling, and as a chromophore extension to enable inversion of the alkene geometry via selective energy transfer catalysis. Mild isomerisation is a pre-condition to access 3-substituted coumarins and provides a handle for divergence. The method is showcased in the synthesis of representative natural products that contain this venerable chemotype. Facile entry into π-expanded estrone derivatives modified at the A-ring is disclosed to demonstrate the potential of the method in bioassay development or in drug repurposing.
?9,11-Estrone derivatives as potential antiproliferative agents: synthesis, in vitro biological evaluation and docking studies
Alves, Gilberto,Canário, Catarina,Falc?o, Amílcar,Matias, Mariana,Santos, Adriana O.,Silvestre, Samuel,de Brito, Vanessa
, p. 211 - 217 (2021/06/25)
A series of ?9,11-estrone derivatives with A- and D-ring modifications has been synthesized and evaluated as antiproliferative agents. The cytotoxicity was assessed in six cell lines (MCF-7, T47-D, LNCaP, HepaRG, Caco-2 and NHDF) by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, and a cell cycle distribution analysis was performed by flow cytometry. Some compounds exhibited relevant cytotoxicity, particularly ?9,11-estrone, which was the most active against HepaRG cells (IC50 = 6.67 μM). Besides the relevance of the double bond in the C-ring, the presence of a 16E-benzylidene group increased the antiproliferative effect on MCF-7 and T47-D cells. Moreover, the introduction of iodine in positions 2 and 4 of estrone seemed to induce a selective cytotoxicity for HepaRG cells. Flow cytometry experiments evidenced a 34% reduction of HepaRG cell viability after treatment with ?9,11-estrone and a cell cycle arrest at the G0/G1 phase. Estrogenic activity was also observed for this compound at 0.1 μM in T47-D cells, and molecular docking studies estimated a marked interaction between this compound and the estrogen receptor α.
Chemoselective Suzuki-Miyaura reactions of 4-bromo-3-O-triflyl-estrone. Synthesis and atropisomerism of arylated estrones
Jopp, Stefan,Wallaschkowski, Tina,Ehlers, Peter,Frank, Eva,Schneider, Gyula,W?lfling, János,Mernyák, Erzsébet,Villinger, Alexander,Langer, Peter
, p. 2825 - 2836 (2018/05/04)
4-Bromo-3-O-triflyl-estrone has been synthesized in 2 steps from estrone and was successfully employed in chemoselective palladium catalysed Suzuki-Miyaura reactions. Mono- and bis-arylations were carried out selectively by variation of ligands and solven
