Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning

Timperley, Christopher M.; Banks, R. E.; Young, Ian; Haszeldine, R. N.

doi:10.1016/j.jfluchem.2011.05.028

Cited by 22 publications

(6 citation statements)

References 37 publications

(51 reference statements)

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“…Abund. To confirm the presence of fluorine atoms in the molecules, we also measured 19 F NMR spectra and performed HRMS instead of elemental analysis. Because some compounds prepared previously by us have not been yet published with 19 F NMR spectra, they are displayed in Table 4.…”

Section: Rel Abund (%)mentioning

confidence: 99%

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Mass spectrometrical and quantum‐chemical study of pentafluorophenylhydrazones

et al. 2020

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Twenty-one pentafluorphenylhydrazones have been analyzed by means of tandem mass spectrometry (ESI MS/MS) conditions to compare their fragmentations with those ones obtained from quantum-chemical calculations of the hydrazone moiety depending on the substitution from the aldehyde site. The hydrazone N-N bond is disrupted under such conditions, and these results are in accordance with the facts that an electron-rich particle, such as an anion and or radical in a solution, can cause this disruption and simultaneous defluorination in para-position of the hydrazone part of the molecule.

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Section: Rel Abund (%)mentioning

confidence: 99%

“…Poly/perfluorinated aromatics are very frequently used substrates for numerous nucleophiles like azides, 5,[13][14][15] nitromethane, [16][17][18] cyanide anion, 19 or other nucleophiles. 20 They are employed as a principal step in the building of selective substituted (hetero)aromatics.…”

Section: Introductionmentioning

confidence: 99%

Mass spectrometrical and quantum‐chemical study of pentafluorophenylhydrazones

et al. 2020

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“…A number of research endeavors have aimed at the improvement of existing antidotes [47,48,49,50,51,52,53,54]. One of the limitations of current AChE reactivators is their ability to cross the blood-brain barrier (BBB), which reduces the amount of reactivator in the brain.…”

Section: Introductionmentioning

confidence: 99%

In Vitro Evaluation of Neutral Aryloximes as Reactivators for Electrophorus eel Acetylcholinesterase Inhibited by Paraoxon

et al. 2019

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Casualties caused by organophosphorus pesticides are a burden for health systems in developing and poor countries. Such compounds are potent acetylcholinesterase irreversible inhibitors, and share the toxic profile with nerve agents. Pyridinium oximes are the only clinically available antidotes against poisoning by these substances, but their poor penetration into the blood-brain barrier hampers the efficient enzyme reactivation at the central nervous system. In searching for structural factors that may be explored in future SAR studies, we evaluated neutral aryloximes as reactivators for paraoxon-inhibited Electrophorus eel acetylcholinesterase. Our findings may result into lead compounds, useful for development of more active compounds for emergencies and supportive care.

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“…Existing methods toward 3-fluoropyridines rely on substitution of the diazonium group (Balz–Schiemann reaction), whereas other transformations such as electrophilic fluorination of organometallics, deoxofluorination, and nucleophilic fluorination (transition-metal-catalyzed, iodine(III) substitution, uncatalyzed halogen substitution) have been occasionally used. Several ring-forming reactions of narrow scope have also been described .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers

et al. 2017

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A method for the synthesis of diversely substituted 3-fluoropyridines from two ketone components is described. The reaction involves photoredox coupling of α,α-difluoro-β-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy) under blue LED irradiation with subsequent one-pot condensation with ammonium acetate. Based on cyclic voltammetry studies, it was determined that α,α-difluoro-β-iodoketones are reduced notably easier compared to 2,2,2-trifluoro-1-iodoethane, which may be ascribed to the influence of the carbonyl group.

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Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning

Cited by 22 publications

References 37 publications

Mass spectrometrical and quantum‐chemical study of pentafluorophenylhydrazones

Mass spectrometrical and quantum‐chemical study of pentafluorophenylhydrazones

In Vitro Evaluation of Neutral Aryloximes as Reactivators for Electrophorus eel Acetylcholinesterase Inhibited by Paraoxon

Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers

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