The Sulfonyl Group and Its Effects in Organic Compounds

Strating, J.

doi:10.1016/b978-1-4831-9982-5.50018-x

Cited by 9 publications

(2 citation statements)

References 55 publications

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“…Attention had earlier been called by Strating to the general role played by electron repulsion in sulfone chemistry. 9 Soon thereafter, Bordwell and Brannen reconciled matters by attributing a relatively minor role to the inductive effect, which is very likely rate enhancing, and a sizable role to the decelerative influences of the field effect. 10 They recognized that the most probable path for attack by a nucleophile on RSO 2 CH 2 Cl requires close approach to at least one atom of high electron density as reflected in 3.…”

Section: Early Observations Of Limited Reactivity In Substitution Reamentioning

confidence: 95%

The Electrophilic and Radical Behavior of α-Halosulfonyl Systems

Paquette

2001

Synlett

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The purpose of this review is to provide an informative backdrop to the susceptibility of a-halosulfonyl compounds to nucleophilic displacement and free radical chemistry. The coverage includes both inter-and intramolecular transformations. While ahalosulfones were initially recognized to exhibit quite low reactivity under S N 2 conditions, this perceived disadvantage can be overcome by making recourse to a polar aprotic solvent such as dimethylformamide. The possible role of steric, electronic, and conformational effects is addressed and shown to differ significantly from the many intramolecular anionic cyclizations that do not exhibit significant kinetic retardation. The data will also show that carbon-carbon bond forming processes under radical conditions are notably clean and efficient reactions. Where ring closures are involved, the adherence to conventional conformational and steric guidelines is shown to be reliable within reasonable limits. These features are expected to contribute to the increased adaptation of electrophilic a-sulfonyl radicals to the solution of synthetic problems.

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Section: Early Observations Of Limited Reactivity In Substitution Reamentioning

confidence: 95%

The Electrophilic and Radical Behavior of α-Halosulfonyl Systems

Paquette

2001

Synlett

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“…The strong electron-withdrawing effect of the sulfonyl group accounts for the tendency of α,β-unsaturated sulfonyls to add to nucleophiles in order to form Michael-type adducts. This property also makes α,β-unsaturated sulfonyls to act as powerful dienophiles [ 180 ]. Several sulfonyl-containing compounds exhibit significant antioxidant and anti-inflammatory activities [ 181 , 182 , 183 , 184 ].…”

Section: αβ-Unsaturated Sulfonylsmentioning

confidence: 99%

An Overview of NRF2-Activating Compounds Bearing α,β-Unsaturated Moiety and Their Antioxidant Effects

Egbujor

Buttari²,

Profumo³

et al. 2022

IJMS

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The surge of scientific interest in the discovery of Nuclear Factor Erythroid 2 (NFE2)-Related Factor 2 (NRF2)-activating molecules underscores the importance of NRF2 as a therapeutic target especially for oxidative stress. The chemical reactivity and biological activities of several bioactive compounds have been linked to the presence of α,β-unsaturated structural systems. The α,β-unsaturated carbonyl, sulfonyl and sulfinyl functional groups are reportedly the major α,β-unsaturated moieties involved in the activation of the NRF2 signaling pathway. The carbonyl, sulfonyl and sulfinyl groups are generally electron-withdrawing groups, and the presence of the α,β-unsaturated structure qualifies them as suitable electrophiles for Michael addition reaction with nucleophilic thiols of cysteine residues within the proximal negative regulator of NRF2, Kelch-like ECH-associated protein 1 (KEAP1). The physicochemical property such as good lipophilicity of these moieties is also an advantage because it ensures solubility and membrane permeability required for the activation of the cytosolic NRF2/KEAP1 system. This review provides an overview of the reaction mechanism of α,β-unsaturated moiety-bearing compounds with the NRF2/KEAP1 complex, their pharmacological properties, structural activity-relationship and their effect on antioxidant and anti-inflammatory responses. As the first of its kind, this review article offers collective and comprehensive information on NRF2-activators containing α,β-unsaturated moiety with the aim of broadening their therapeutic prospects in a wide range of oxidative stress-related diseases.

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Braverman

1990

Sulphinic Acids, Esters and Derivatives (1990)

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The Sulfonyl Group and Its Effects in Organic Compounds

Cited by 9 publications

References 55 publications

The Electrophilic and Radical Behavior of α-Halosulfonyl Systems

The Electrophilic and Radical Behavior of α-Halosulfonyl Systems

An Overview of NRF2-Activating Compounds Bearing α,β-Unsaturated Moiety and Their Antioxidant Effects

Rearrangements

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