ChemInform Abstract: Direct C‐Nitration of Cyclic α,β‐Unsaturated Oximes under the Action of Sodium Nitrite and Acetic Acid in Methanol.

Chibiryaev, A. M.; Denisov, A. Yu.; Пышный, Д. В.; Ткачев, А. В.

doi:10.1002/chin.200222170

Cited by 2 publications

(5 citation statements)

References 1 publication

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“…The crude product was purified by recrystallization from hexanes affording 6 as a pale yellow solid (0.86 g, 51%). NMR spectral data were consistent with literature data for 6 …”

Section: Methodssupporting

confidence: 86%

“…The E -isomer was preferentially formed in all cases and exclusively for 4 and 6 , as this minimizes steric interactions between the hydroxyl group of the oxime and the proximal hydrogen or methyl substituent in the α-position. The microwave-assisted heating allowed the preparation of 3 – 7 with reduced reaction times compared to previously reported procedures. – …”

Section: Resultsmentioning

confidence: 99%

“…The microwaveassisted heating allowed the preparation of 3-7 with reduced reaction times compared to previously reported procedures. [30][31][32][33] Skin Sensitizing Potency. Currently, the murine LLNA 34 is the method of choice for identification and potency assessment of contact allergens and was used to determine the sensitizing potency of oximes 2-8 (Figure 1, Table S1, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…NMR spectral data were consistent with literature data for 4. 31 3-Methylcyclohex-2-enone Oxime (5). 3-Methylcyclohex-2enone (1.76 g, 16 mmol) was reacted as described in the general procedure.…”

Section: Methodsmentioning

confidence: 99%

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Oximes: Metabolic Activation and Structure−Allergenic Activity Relationships

et al. 2008

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Metabolic activation of chemicals (prohaptens) in the skin can cause allergic contact dermatitis. We have explored structure-allergenic activity relationships for seven potential oxime prohaptens using the local lymph node assay and a GSH trapping screen with liver microsomes. The general structure-allergenic activity relationships found were that an alpha,beta-unsaturation is necessary for an oxime to be a prohapten and that increased steric hindrance around this double bond leads to reduction in sensitizing capacity. We also found that sensitizing oximes can be distinguished in vitro from nonsensitizers by monitoring of mono-oxidized (+16 Da) GSH conjugates in the GSH trapping screen. However, care should be taken when interpreting data from GSH trapping screens, as nonsensitizers may also form GSH conjugates via alternative mechanisms. This investigation emphasizes the importance of considering cutaneous bioactivation in toxicity assessment of chemicals used in contact with the skin.

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“…The crude product was purified by recrystallization from hexanes affording 6 as a pale yellow solid (0.86 g, 51%). NMR spectral data were consistent with literature data for 6 …”

Section: Methodssupporting

confidence: 86%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Oximes: Metabolic Activation and Structure−Allergenic Activity Relationships

et al. 2008

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“…Cyclic α,β-unsaturated oximes of the terpene series may be converted into the corresponding β-hydroxyimino-nitroalkenes under the action of sodium nitrite and acetic acid in methanol (Scheme ) …”

Section: Main Secondary Targets Of Nitritementioning

confidence: 99%

Secondary Targets of Nitrite-Derived Reactive Nitrogen Species: Nitrosation/Nitration Pathways, Antioxidant Defense Mechanisms and Toxicological Implications

d’Ischia

Napolitano

Manini

et al. 2011

Chem. Res. Toxicol.

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Nitrite, the primary metabolite of nitric oxide (NO) and a widely diffused component of human diet, plays distinct and increasingly appreciated roles in human physiology. However, when exposed to acidic environments, typically in the stomach, or under oxidative stress conditions, it may be converted to a range of reactive nitrogen species (RNS) which in turn can target a variety of biomolecules. Typical consequences of toxicological relevance include protein modification, DNA base deamination and the formation of N-nitrosamines, among the most potent mutagenic and carcinogenic compounds for humans. Besides primary biomolecules, nitrite can cause structural modifications to a variety of endogenous and exogenous organic compounds, ranging from polyunsaturated fatty acids to estrogens, tocopherol, catecholamines, furans, retinoids, dietary phenols, and a range of xenobiotics. The study of the interactions between nitrite and key food components, including phenolic antioxidants, has therefore emerged as an area of great promise for delineating innovative strategies in cancer chemoprevention. Depending on substrates and conditions, diverse reaction pathways may compete to determine product features and distribution patterns. These include nitrosation and nitration but also oxidation, via electron transfer to nitrosonium ion or nitrogen dioxide. This contribution aims to provide an overview of the main classes of compounds that can be targeted by nitrite and to discuss at chemical levels the possible reaction mechanisms under conditions that model those occurring in the stomach. The toxicological implications of the nitrite-modified molecules are finally addressed, and a rational chemical approach to the design of potent antinitrosing agents is illustrated.

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ChemInform Abstract: Direct C‐Nitration of Cyclic α,β‐Unsaturated Oximes under the Action of Sodium Nitrite and Acetic Acid in Methanol.

Cited by 2 publications

References 1 publication

Oximes: Metabolic Activation and Structure−Allergenic Activity Relationships

Oximes: Metabolic Activation and Structure−Allergenic Activity Relationships

Secondary Targets of Nitrite-Derived Reactive Nitrogen Species: Nitrosation/Nitration Pathways, Antioxidant Defense Mechanisms and Toxicological Implications

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