Mechanistic studies of fluorodecarboxylation with xenon difluoride

Patrick, Timothy B.; Khazaeli, Sadegh; Nadji, Sourena; Hering-Smith, Katy; Reif, Dirk

doi:10.1021/jo00055a026

Cited by 64 publications

(48 citation statements)

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“…1, C and D; synthetic schemes shown in Figs. 3 and 4 and characterization outlined under "Experimental Procedures") (21)(22)(23). The first, a demethyl analog of tiopronin (termed demethyl tiopronin) was synthesized without the methyl substituent alpha to the thiol (Fig.…”

Section: Glutathione Peroxidase Inhibitors Elicit Cs-mentioning

confidence: 99%

Inhibition of Glutathione Peroxidase Mediates the Collateral Sensitivity of Multidrug-resistant Cells to Tiopronin

Hall

Marshall

Kwit

et al. 2014

Journal of Biological Chemistry

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Background: Tiopronin is a small molecule that selectively kills multidrug-resistant cancer cells. Results: Inhibition of glutathione peroxidase by tiopronin leads to elevated reactive oxygen species in MDR cells. Conclusion: Tiopronin mediates the killing of MDR cells by inhibition of glutathione peroxidases.Significance: Glutathione peroxidase inhibition may be a viable strategy for modulation of multidrug resistance in cancer.

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Section: Glutathione Peroxidase Inhibitors Elicit Cs-mentioning

confidence: 99%

Inhibition of Glutathione Peroxidase Mediates the Collateral Sensitivity of Multidrug-resistant Cells to Tiopronin

Hall

Marshall

Kwit

et al. 2014

Journal of Biological Chemistry

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“…30 In a series of detailed studies Patrick and co-workers had previously shown that reaction of carboxylic acids with XeF 2 in CH 2 Cl 2 solution in polyethylene flasks gave fluorides [RCO 2 H → RF]. [31][32][33] We therefore undertook a comparison of the reactions of carboxylic acids with XeF 2 in (i) CH 2 Cl 2 /PTFE and (ii) CH 2 Cl 2 /Pyrex. 30 Results of these studies are summarised in Table 2.…”

Section: Methodsmentioning

confidence: 99%

Xenon difluoride in the organic laboratory: a tale of substrates, solvents and vessels

Ramsden¹

2013

Arkivoc

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This Account summarises a series of studies of the reactions of xenon difluoride with organic substrates. It is concluded that xenon difluoride has two initial modes of reaction with organic substrates: single electron transfer (SET) and electrophilic addition. Reactions of aryltrimethylsilanes, carboxylic acids and esters, and trimethylsilyl enol ethers are discussed. The mode of reaction is determined by a combination of the solvent, the reaction vessel material and the presence of an acid catalyst. Pyrex, in the form of a flask surface, is a very effective catalyst for electrophilic reactions but this effect is inhibited by use of acetonitrile as solvent. Trimethylsilyl derivatives are particularly convenient substrates as these avoid the formation of HF, which may catalyse side-reactions. Some studies using [ 18 F]-XeF 2 are described.

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“…The dimerization process is observed in the reaction of 3-phenylbicyclo[1.1.1]pentan-1-oicacid, and free radical intermediates were suggested 36,37 ; however, only a reduction process was found by Della and Head 38 and Michl and coworkers 39 . Reaction of various bridged carboxylic acids with xenon difluoride gives, beside fluoro-substituted products, also reduced products, while the product distribution depends on the structure of the alkane 37,38 (Scheme 10).…”

Section: Reactions a Reactions Of Xenon Fluorides With Alkanesmentioning

confidence: 99%