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Acetonitrile Oxide

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Julio Casado – One of the best experts on this subject based on the ideXlab platform.

  • Sorbate−Nitrite Interactions: Acetonitrile Oxide as an Alkylating Agent
    Chemical research in toxicology, 2009
    Co-Authors: M. Teresa Pérez-prior, Rafael Gómez-bombarelli, Marina González-pérez, José A. Manso, M. Pilar García-santos, Emilio Calle, Julio Casado
    Abstract:

    Because chemical species with DNA-damaging and mutagenic activity are formed in sorbate−nitrite mixtures and because sorbic acid sometimes coexists with nitrite occurring naturally or incorporated as a food additive, the study of sorbate−nitrite interactions is important. Here, the alkylating potential of the products resulting from such interactions was investigated. Drawn were the following conclusions: (i) Acetonitrile Oxide (ACNO) is the compound responsible for the alkylating capacity of sorbate−nitrite mixtures; (ii) ACNO alkylates 4-(p-nitrobenzyl)pyridine (NBP), a trap for alkylating agents with nucleophilic characteristics similar to those of DNA bases, forming an adduct (AD; e = 1.4 × 104 M−1 cm−1; λ = 519 nm); (iii) the NBP alkylation reaction complies with the rate equation, r = d[AD]/dt = kalkACNO[ACNO][NBP] − khydAD[AD], kalkACNO being the NBP alkylation rate constant for ACNO and khydAD the rate constant for the adduct hydrolysis reaction; (iv) the small fraction of ACNO forming the adduct …

  • sorbate nitrite interactions Acetonitrile Oxide as an alkylating agent
    Chemical Research in Toxicology, 2009
    Co-Authors: Teresa M Perezprior, José A. Manso, Emilio Calle, Rafael Gomezbombarelli, Marina Gonzalezperez, Pilar M Garciasantos, Julio Casado
    Abstract:

    Because chemical species with DNA-damaging and mutagenic activity are formed in sorbate−nitrite mixtures and because sorbic acid sometimes coexists with nitrite occurring naturally or incorporated as a food additive, the study of sorbate−nitrite interactions is important. Here, the alkylating potential of the products resulting from such interactions was investigated. Drawn were the following conclusions: (i) Acetonitrile Oxide (ACNO) is the compound responsible for the alkylating capacity of sorbate−nitrite mixtures; (ii) ACNO alkylates 4-(p-nitrobenzyl)pyridine (NBP), a trap for alkylating agents with nucleophilic characteristics similar to those of DNA bases, forming an adduct (AD; e = 1.4 × 104 M−1 cm−1; λ = 519 nm); (iii) the NBP alkylation reaction complies with the rate equation, r = d[AD]/dt = kalkACNO[ACNO][NBP] − khydAD[AD], kalkACNO being the NBP alkylation rate constant for ACNO and khydAD the rate constant for the adduct hydrolysis reaction; (iv) the small fraction of ACNO forming the adduct …

Olga Pudova – One of the best experts on this subject based on the ideXlab platform.

  • cytotoxic activity of silyl and germyl substituted 4 4 dioxo 3a 6a dihydrothieno 2 3 d isoxazolines 2
    Metal-based Drugs, 2000
    Co-Authors: E. Lukevics, Pavel Arsenyan, Irina Shestakova, Olga Zharkova, I Kanepe, R Mezapuke, Olga Pudova
    Abstract:

    The [2+3] dipolar cycloaddition of nitrile Oxides to the double C = C bonds of thiophene-1, 1-diOxides leads to formation of the fused isoxazolines-2 (1, 2). Tumor growth inhibition of these compounds strongly depends on the nature of group IV A element increasing from slightly active tert-butyl derivatives to silicon and germanium containing analogues. The products of benzonitrile Oxide cycloaddition have greater cytotoxic effect than the compounds obtained from the cycloaddition reaction of 2, 5-disubstituted thiophene-1, 1-diOxides with Acetonitrile Oxide. Fused silyl substituted isoxazolines-2 are stronger NO-inducers than their germyl and tert-butyl analogues.

  • Cycloaddition Reactions of Nitrile Oxides to 2,4-Silyl- and Germyl-Substituted Thiophene-1,1-diOxides
    Organometallics, 1999
    Co-Authors: Edmunds Lukevics, Pavel Arsenyan, Sergey Belyakov, And Juris Popelis, Olga Pudova
    Abstract:

    2,4-Silyl- and germyl-substituted thiophene-1,1-diOxides as well as 5,5‘- and 4,4‘-bis(trimethylsilyl)-2,2‘-bithiophene-1,1-diOxides were prepared from the corresponding thiophenes and bithiophenes by oxidation with m-CPBA in CH2Cl2 at room temperature. The [2+3] dipolar cycloaddition of nitrile Oxides to the double CC bonds of thiophene-1,1-diOxides has been investigated. It was shown that in the series of 2,4-disubstituted thiophene-1,1-diOxides only the C(4)C(5) double bond interacts with Acetonitrile Oxide to give fused thienoisoxazolines. Addition of Acetonitrile Oxide to 5,5‘-bis(trimethylsilyl)-2,2‘-bithiophene-1,1-diOxide was accompanied by desilylation. Isomeric 4,4‘-bis(trimethylsilyl)-2,2‘-bithiophene-1,1-diOxide was inactive in the reaction with Acetonitrile Oxide. Cycloaddition of benzonitrile Oxide with all mentioned sulfones did not occur. The molecular structures of 2,4-bis(trimethylsilyl)thiophene-1,1-diOxide, 2-trimethylgermyl-4-trimethylsilylthiophene-1,1-diOxide, 2-trimethylsilyl-4-tri…

Emilio Calle – One of the best experts on this subject based on the ideXlab platform.

  • Sorbate−Nitrite Interactions: Acetonitrile Oxide as an Alkylating Agent
    Chemical research in toxicology, 2009
    Co-Authors: M. Teresa Pérez-prior, Rafael Gómez-bombarelli, Marina González-pérez, José A. Manso, M. Pilar García-santos, Emilio Calle, Julio Casado
    Abstract:

    Because chemical species with DNA-damaging and mutagenic activity are formed in sorbate−nitrite mixtures and because sorbic acid sometimes coexists with nitrite occurring naturally or incorporated as a food additive, the study of sorbate−nitrite interactions is important. Here, the alkylating potential of the products resulting from such interactions was investigated. Drawn were the following conclusions: (i) Acetonitrile Oxide (ACNO) is the compound responsible for the alkylating capacity of sorbate−nitrite mixtures; (ii) ACNO alkylates 4-(p-nitrobenzyl)pyridine (NBP), a trap for alkylating agents with nucleophilic characteristics similar to those of DNA bases, forming an adduct (AD; e = 1.4 × 104 M−1 cm−1; λ = 519 nm); (iii) the NBP alkylation reaction complies with the rate equation, r = d[AD]/dt = kalkACNO[ACNO][NBP] − khydAD[AD], kalkACNO being the NBP alkylation rate constant for ACNO and khydAD the rate constant for the adduct hydrolysis reaction; (iv) the small fraction of ACNO forming the adduct …

  • sorbate nitrite interactions Acetonitrile Oxide as an alkylating agent
    Chemical Research in Toxicology, 2009
    Co-Authors: Teresa M Perezprior, José A. Manso, Emilio Calle, Rafael Gomezbombarelli, Marina Gonzalezperez, Pilar M Garciasantos, Julio Casado
    Abstract:

    Because chemical species with DNA-damaging and mutagenic activity are formed in sorbate−nitrite mixtures and because sorbic acid sometimes coexists with nitrite occurring naturally or incorporated as a food additive, the study of sorbate−nitrite interactions is important. Here, the alkylating potential of the products resulting from such interactions was investigated. Drawn were the following conclusions: (i) Acetonitrile Oxide (ACNO) is the compound responsible for the alkylating capacity of sorbate−nitrite mixtures; (ii) ACNO alkylates 4-(p-nitrobenzyl)pyridine (NBP), a trap for alkylating agents with nucleophilic characteristics similar to those of DNA bases, forming an adduct (AD; e = 1.4 × 104 M−1 cm−1; λ = 519 nm); (iii) the NBP alkylation reaction complies with the rate equation, r = d[AD]/dt = kalkACNO[ACNO][NBP] − khydAD[AD], kalkACNO being the NBP alkylation rate constant for ACNO and khydAD the rate constant for the adduct hydrolysis reaction; (iv) the small fraction of ACNO forming the adduct …