Synthesis of β-Hydroxy-α,α-difluorosulfonamides from Carbanions of Difluoromethanesulfonamides

Soley, Jacob; Taylor, Scott D.

doi:10.1021/acs.joc.1c00378

Cited by 2 publications

(2 citation statements)

References 40 publications

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“…To date, C-H activation of the methylene group of 2-oxo-2-phenylethanesulfonamide ( 6 ), an example of β-ketosulfonamides, is presented by a reaction with isatoic anhydride and electrophilic fluorination [ 51 , 52 ]. In this study, we explored the possibility of using compound 6 as a methylene component in the Knoevenagel reaction to obtain chalconesulfonamide 7 .…”

Section: Discussionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Chalconesulfonamides: En Route to Proapoptotic Agents with Antiestrogenic Potency

Krymov,

Salnikova,

Dezhenkova

et al. 2023

Pharmaceuticals

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Breast and other estrogen receptor α-positive cancers tend to develop resistance to existing drugs. Chalcone derivatives possess anticancer activity based on their ability to form covalent bonds with targets acting as Michael acceptors. This study aimed to evaluate the anticancer properties of a series of chalcones (7a–l) with a sulfonamide group attached to the vinyl ketone moiety. Chalconesulfonamides showed a potent antiproliferative effect at low micromolar concentrations against several cancer cell lines, including ERα-positive 4-hydroxytamoxifen-resistant MCF7/HT2. Immunoblotting of samples treated with the lead compound 7e revealed its potent antiestrogenic activity (ERα/GREB1 axis) and induction of PARP cleavage (an apoptosis marker) in breast cancer cells. The obtained compounds represent a promising basis for further development of targeted drugs blocking hormone pathways in cancer cells.

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Section: Discussionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Chalconesulfonamides: En Route to Proapoptotic Agents with Antiestrogenic Potency

Krymov,

Salnikova,

Dezhenkova

et al. 2023

Pharmaceuticals

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“…In many cases, the two bases are functionally interchangeable . In others, KHMDS offered inferior or superior yields, inferior or superior selectivities, superior yields at the expense of inferior selectivities, and vice versa . Of course, it is often unclear whether the results stem from the disilazide bases or from the resulting alkali-metal-salt intermediates.…”

Section: Introductionmentioning

confidence: 99%

Potassium Hexamethyldisilazide (KHMDS): Solvent-Dependent Solution Structures

Spivey,

Collum

2024

J. Am. Chem. Soc.

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Solution structures of potassium hexamethyldisilazide [KHMDS] and labeled [ 15 N]KHMDS were examined using a number of analytical methods including 29 Si NMR spectroscopy and density functional theory computations. A combination of 15 N− 29 Si couplings, 29 Si chemical shifts, and the method of continuous variations reveals dimers, monomers, and ion pairs. Weakly coordinating monofunctional ligands such as toluene, N,N-dimethylethylamine, and Et 3 N afford exclusively dimers. 1,3-Dioxolane, THF, dimethoxyethane, hexamethylphosphoramide, and diglyme provide dimers at low ligand concentrations and monomers at high ligand concentrations. N,N,N′,N'-Tetramethylethylenediamine and N,N,N′,N'-tetramethylcyclohexanediamine provide exclusively dimers at all ligand concentrations at ambient temperatures and significant monomer at −80 °C. Studies of 12-crown-4 ran into technical problems. Equimolar 15crown-5 forms a dimer, whereas excess 15-crown-5 affords a putative ion pair. Whereas equimolar 18-crown-6 also affords a dimer, an excess provides a monomer rather than a solvent-separated ion pair. [2.2.2]cryptand affords what is believed to be a contact-ionpaired cryptate. Solvation was probed using largely density functional theory (DFT) computations. Thermally corrected energies are consistent with lower aggregates and higher solvates at low temperatures, but the magnitudes of the computed temperature dependencies were substantially larger than the experimentally derived data.

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Synthesis of β-Hydroxy-α,α-difluorosulfonamides from Carbanions of Difluoromethanesulfonamides

Cited by 2 publications

References 40 publications

Synthesis and Biological Evaluation of Chalconesulfonamides: En Route to Proapoptotic Agents with Antiestrogenic Potency

Synthesis and Biological Evaluation of Chalconesulfonamides: En Route to Proapoptotic Agents with Antiestrogenic Potency

Potassium Hexamethyldisilazide (KHMDS): Solvent-Dependent Solution Structures

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