Potent hydrophilic dienophiles. Synthesis and aqueous stability of several 4-aryl- and sulfonated 4-aryl-1,2,4-triazoline-3,5-diones and their immobilization on silica gel

Keana, John F. W.; Guzikowski, Anthony P.; Ward, David D.; Morat, Claude; Nice, Faith L. Van

doi:10.1021/jo00164a005

Cited by 23 publications

(24 citation statements)

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“…Compound 10 was prepared by a slight modification of the reported literature procedure [31] for the preparation of triazolinedione derivatives (see the Supporting Information for synthetic schemes). Compounds (1--9) were available commercially and Scheme 4.…”

Section: Methodsmentioning

confidence: 99%

Dynamic Covalent Chemistry: A Facile Room‐Temperature, Reversible, Diels–Alder Reaction between Anthracene Derivatives and N‐Phenyltriazolinedione

Roy

Lehn

2011

Chemistry An Asian Journal

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A series of readily accessible, dynamic Diels-Alder reactions that are reversible at room temperature have been developed between anthracene derivatives as dienes and N-phenyl-1,2,4-triazoline-3,5-dione as the dienophile. The adducts formed undergo reversible component exchange to form dynamic libraries of equilibrating cycloadducts. Furthermore, reversible adduct formation allows temperature-dependent modulation of the fluorescent properties of anthracene components; a feature of potential interest for the design of optodynamic polymeric materials by careful selection and manipulation of these simple dienes and dienophiles.

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Section: Methodsmentioning

confidence: 99%

Dynamic Covalent Chemistry: A Facile Room‐Temperature, Reversible, Diels–Alder Reaction between Anthracene Derivatives and N‐Phenyltriazolinedione

Roy

Lehn

2011

Chemistry An Asian Journal

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“…Stable nitroxide radicals are used intensively as probes for measurement of oxygen [1, 2], pH [3–5], glutathione [6, 7], redox state [8, 9] in living tissues, for structural studies of biological macromolecules [10], as magnetic resonance imaging contrast agents [11, 12] and in other fields [13–16]. The nitroxide radicals of imidazoline and imidazolidine types were shown to reveal the changes in their electron paramagnetic resonance (EPR) spectra due to reversible protonation of N-3 nitrogen [17] of the radical heterocycle and are widely used as pH-probes [4, 5, 14, 15].…”

Section: Introductionmentioning

confidence: 99%

EPR and Quantum Chemical Studies of the pH-sensitive Imidazoline and Imidazolidine Nitroxides with Bulky Substituents

et al. 2010

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The X- and W-band electron paramagnetic resonance (EPR) spectroscopies were employed to investigate a series of imidazolidine nitroxide radicals with different number of ethyl and methyl substituents at positions 2 and 5 of a heterocycle in liquid and frozen solutions. The influence of the substituents on the line shape and width was studied experimentally and analyzed using quantum chemical calculations. Each pair of the geminal ethyl groups in the positions 2 or 5 of the imidazolidine ring was found to produce an additional hyperfine splitting (hfs) of about 0.2 mT in the EPR spectra of the nitroxides. The effect was attributed to the hfs constant of only one of four methylene hydrogen atoms of two geminal ethyl substituents not fully averaged by ethyl group rotation and ring puckering. In accordance with this assumption, the substitution of hydrogen atoms of CH2 groups in 2,2,5,5-tetraethyl-substituted imidazolidine nitroxides by deuterium leads to the substantial narrowing of EPR lines which could be useful for many biochemical and biomedical applications, including pH-monitoring. W-band EPR spectra of 2,2,5,5-tetraethyl-substituted imidazolidine nitroxide and its 2,2,5,5-tetraethyl–d8 deuterium-substituted analog measured at low temperatures demonstrated high sensitivity of their g-factors to pH, which indicates their applicability as spin labels possessing high stability.

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“…Diazodicarbonyl compounds showed promising kinetics but were not sufficiently stable in water for biological applications. ( 15 ) α-Fluoroketones and fluorinated alkenes and alkynes reacted with quadricyclane too slowly for practical utility, and some of these reagents were prone to side reactions. One reagent stood out as a promising lead: bis(dithiobenzil)nickel(II) ( 2 ), a Ni bis(dithiolene) complex that reacted cleanly with 7-acetoxyquadricyclane ( 1 ) to yield adduct 3 (Figure 1 B).…”

mentioning

confidence: 99%

A Bioorthogonal Quadricyclane Ligation

Sletten

Bertozzi

2011

J. Am. Chem. Soc.

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New additions to the bioorthogonal chemistry compendium can advance biological research by enabling multiplexed analysis of biomolecules in complex systems. Here we introduce the quadricyclane ligation, a new bioorthogonal reaction between the highly strained hydrocarbon quadricyclane and Ni bis(dithiolene) reagents. This reaction has a second-order rate constant of 0.25 M–1 s–1, on par with fast bioorthogonal reactions of azides, and proceeds readily in aqueous environments. Ni bis(dithiolene) probes selectively labeled quadricyclane-modified bovine serum albumin, even in the presence of cell lysate. We have demonstrated that the quadricyclane ligation is compatible with, and orthogonal to, strain-promoted azide–alkyne cycloaddition and oxime ligation chemistries by performing all three reactions in one pot on differentially functionalized protein substrates. The quadricyclane ligation joins a small but growing list of tools for the selective covalent modification of biomolecules.

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Potent hydrophilic dienophiles. Synthesis and aqueous stability of several 4-aryl- and sulfonated 4-aryl-1,2,4-triazoline-3,5-diones and their immobilization on silica gel

Abstract: Hungary, for a postdoctoral leave of absence.

Cited by 23 publications

References 0 publications

Dynamic Covalent Chemistry: A Facile Room‐Temperature, Reversible, Diels–Alder Reaction between Anthracene Derivatives and N‐Phenyltriazolinedione

Dynamic Covalent Chemistry: A Facile Room‐Temperature, Reversible, Diels–Alder Reaction between Anthracene Derivatives and N‐Phenyltriazolinedione

EPR and Quantum Chemical Studies of the pH-sensitive Imidazoline and Imidazolidine Nitroxides with Bulky Substituents

A Bioorthogonal Quadricyclane Ligation

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