ChemInform Abstract: A NEW SYNTHESIS OF O‐ALKYLHYDROXYLAMINES

Grochowski, E.; Jurczak, Janusz

doi:10.1002/chin.197701184

Cited by 6 publications

(13 citation statements)

References 1 publication

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“…N -[2-(Aminooxy)ethyl]- N,N -dimethyl-1-dodecylammonium iodide (QDA ) and *QDA ( 13 CD 3 -labeled QDA) were prepared as outlined in Scheme S1 (Supplementary information) according to our previously published method (Biswas et al , 2010) for the synthesis of structurally related aminooxy compounds using the Mitsunobu approach originally described by Grochowski and Jurczak (1976). Full experimental and characterization details are provided in the Supplementary Information.…”

Section: Methodsmentioning

confidence: 99%

A carbonyl capture approach for profiling oxidized metabolites in cell extracts

Mattingly

Nantz

et al. 2012

Metabolomics

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Fourier-transform ion-cyclotron resonance mass spectrometry (FT-ICR-MS) detection of oxidized cellular metabolites is described using isotopologic, carbonyl-selective derivatizing agents that integrate aminooxy functionality for carbonyl capture, quaternary nitrogen for electrospray enhancement, and a hydrophobic domain for sample cleanup. These modular structural features enable rapid, sensitive analysis of complex mixtures of metabolite-derivatives by FT-ICR-MS via continuous nanoelectrospray infusion. Specifically, this approach can be used to globally assess levels of low abundance and labile aldehyde and ketone metabolites quantitatively and in high throughput manner. These metabolites are often key and unique indicators of various biochemical pathways and their perturbations. Analysis of lung adenocarcinoma A549 cells established a profile of carbonyl metabolites spanning multiple structural classes. We also demonstrate a procedure for metabolite quantification using pyruvate as a model analyte.

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Section: Methodsmentioning

confidence: 99%

A carbonyl capture approach for profiling oxidized metabolites in cell extracts

Mattingly

Nantz

et al. 2012

Metabolomics

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“…The EtOAc layer was washed with brine and dried (MgSO,). The solvent was evaporated and the residue was triturated with Et2O to afford a N-protected cephalosporin derivative (15).…”

Section: Preparation Of Ethyl 2-(2-formamido-4-thiazolyl)glyoxalate (3)mentioning

confidence: 99%

Studies on .BETA.-lactam antibiotics. VII. Effect on antibacterial activity of the oxime O-substituents with various functional groups in the 7.BETA.-((Z)-2-(2-amino-4-thiazolyl)-2-oxyiminoacetamido)cephalosporins.

et al. 1983

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The synthesis and in vitro activity of the 7-[O-substituted oxyiminoacetamido]cephalosporins (I) without substitution at 3-position of a cephem nucleus are described. Effect of changing the oxime O-substituents (R1) with various functional groups in the 7-acyl residue on antibacterial activity was examined. Against Gram-positive bacteria, cephems with hydrophilic functions in the R' moiety such as hydroxyethyl, aminoethyl and carboxymethyl groups showed decrease of the activity, while cephems with lipophilic functions such as cyanomethyl, methylthiomethyl and halogenoethyl groups exhibited increase of the activity. However, influence of the substituents (R1) on activity against Gram-negative bacteria was observed to be relatively independent of the nature of their functional groups.

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“…The syntheses of the O-substituted oximes of tropinone and N-methyl-4-piperidinone are outlined in Scheme 1. The intermediate N-alkynylphthalimides (6)(7)(8)(9)(10)(11)(12)(13)(14) are synthesized from the reaction of diethyl azodicarboxylate and triphenylphosphine (to form a betaine), an alcohol, and the nucleophilic N-hydroxyphthalimide. 13,14 Hydrazinolysis of the intermediate N-(alkynyloxy)phthalimides was attempted by various methods such as refluxing/stirring with hydrazine hydrate in ethanol or pyridine.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Pharmacological Characterization of O-Alkynyloximes of Tropinone and N-Methylpiperidinone as Muscarinic Agonists

1998

J. Med. Chem.

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A number of O-alkynyloximes of tropinone and N-methyl-4-piperidinone have been synthesized and evaluated for muscarinic activity. The affinities of these oximes were tested in homogenates of cerebral cortex, heart, and submandibulary glands from rats using [3H]pirenzepine and [3H]-N-methylscopolamine as radioligands. The oximes bind to the cortical muscarinic receptors with pKi values varying from 3 to 7. Higher binding affinities were observed for the O-alkynyl tropinone oximes than the corresponding piperidinone analogues. Binding to the muscarinic sites in the heart and submandibulary glands was also observed but with lower affinities. Good M1 subtype selectivity (10-fold or greater) was observed with some oximes (26a, 28a, 32a) at the cortical sites. These oximes also attenuated scopolamine-induced impairment of the water mask task in mice. Functional assays for M3 activity on the rat aorta showed that all oximes possessed M3 agonist action but M2 agonist activity was not observed at the endothelium-denuded rabbit aorta. Analysis of the quantitative structure-activity relationship (QSAR) indicated that the Connolly surface area is an important determinant of activity, accounting for 70% of the variation in cortical binding affinity among the oximes.

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ChemInform Abstract: A NEW SYNTHESIS OF O‐ALKYLHYDROXYLAMINES

Abstract: Alkohole (I) werden mit N‐Hydroxyphthalimid (II) in Gegenwart des Betains (III) zu N‐Alkoxyphthalimiden (IV) kondensiert, aus denen durch weitere Umsetzung mit Hydrazin die O‐Alkylhydroxylarnine (V) freigesetzt werden.

Cited by 6 publications

References 1 publication

A carbonyl capture approach for profiling oxidized metabolites in cell extracts

A carbonyl capture approach for profiling oxidized metabolites in cell extracts

Studies on .BETA.-lactam antibiotics. VII. Effect on antibacterial activity of the oxime O-substituents with various functional groups in the 7.BETA.-((Z)-2-(2-amino-4-thiazolyl)-2-oxyiminoacetamido)cephalosporins.

Synthesis and Pharmacological Characterization of O-Alkynyloximes of Tropinone and N-Methylpiperidinone as Muscarinic Agonists

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