Studies on chemical carcinogens. XXI. Quantitative structure-mutagenicity relationship among substituted styrene oxides.

Tamura, Naotoshi; Takahashi, Kazuhiko; Shirai, Naohiro; Kawazoe, Yutaka

doi:10.1248/cpb.30.1393

Cited by 20 publications

(23 citation statements)

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“…Sugiura et al (1978a) reported that the mutagenicity of their compounds depended only on the reactivity at the benzylic, a(CH)epoxide carbon site and that reactivity at the fl(CH2) site as well as the partition coefficients of their epoxides appeared to have no effect. Tamura et al (1982) in an extended series of styrene oxide compounds, confirmed that the electrophilic reaction of the a-CH carbon, as indicated by Hammett's o values (McDaniel and Brown, 1958) for electronic effects of their para-styrene substituents, was a factor in the relative mutagenicities of their compounds. However, they also as-0165-1218/86/$03.50 © 1986 Elsevier Science Publishers B.V. (Biomedical Division) b See McDaniel and Brown (1958).…”

mentioning

confidence: 66%

“…The position of nucleophilic attack of pyridine on the epoxide ring of the a-methylstyrene oxides was determined by the NMR method of Tamura et al (1982) in which the products could be formed. In contrast to the styrene oxide series only product A could be detected on the basis of methylene protons at 8 4.9 to 5.0 and not at 8 4.4 to 4.6.…”

Section: Resultsmentioning

confidence: 99%

“…Thus, all the alkylation occurs at the less hindered r-carbon and the effect of the para substituent on the distribution between aand r-carbon products as noted in the styrene oxide series is eliminated. Mutagenicity testing with the TA100 and TA1535 strains of Salmonella typhimurium was performed in the liquid preincubation version of the Ames procedure as has been reported (Sugiura et al, 1978a(Sugiura et al, , 1981Tamura et al, 1982) for the mutagenicity testing of the parent styrene oxide series. The TA100 results for our a-methyl series are given in Table 2 and the dose-response curves expressed in mean number of revertants are compared in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…There was no demonstrable mutagenicity for the para-bromo derivative at any dose. Tamura et al (1982) examined the parent styrene oxide series for correlations of relative…”

Section: Resultsmentioning

confidence: 99%

“…It was expected that disubstitution on the a carbon would increase nucleophilic attack at the CH 2 carbon of the epoxides. Thus, the effect of such substitution would be on reactivity between the a and fl sites without major effect on the relative influence of electrophilicity, molecular volume or hydrophilicity, the factors used in the styrene oxide study of Tamura et al (1982).…”

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confidence: 99%

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Mutagenicity of para-substituted α-methylstyrene oxide derivatives with Salmonella

Rosman

Beylin

Gaddamidi

et al. 1986

Mutation Research/Genetic Toxicology

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A series of 5 para-substituted alpha-methylstyrene oxide derivatives have been synthesized and together with alpha-methylstyrene oxide as well as styrene oxide have been studied as to their mutagenicity with the TA100 and TA1535 strains of Salmonella typhimurium. A multiple regression analysis model has been developed which describes the mutagenicity of the alpha-methylstyrene oxides in TA100. An increase in van der Waals volume was the most important variable in the model with greater improvement occurring with inclusion of the Hammett values for the para substituents on the compounds. The alpha-methylstyrene oxides were less active alkylating agents with 4-(p-nitrobenzyl)pyridine than styrene oxide and with pyridine all reactivity was at the beta-epoxide carbon. However all the alpha-methylstyrene oxide derivatives, except for the bromo compound where toxicity was evident, showed mutagenicity values either greater or comparable to that of styrene oxide. These studies would indicate that reactivity at the beta-carbon should also be a factor in describing the mutagenicity of the parent styrene oxide series.

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confidence: 66%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…There was no demonstrable mutagenicity for the para-bromo derivative at any dose. Tamura et al (1982) examined the parent styrene oxide series for correlations of relative…”

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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Mutagenicity of para-substituted α-methylstyrene oxide derivatives with Salmonella

Rosman

Beylin

Gaddamidi

et al. 1986

Mutation Research/Genetic Toxicology

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4‐Oxiranylbenzonitrile 52695‐39‐3

2004

Sax's Dangerous Properties of Industrial Materials

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Quaternary Chiral β^2,2‐Amino Acids with Pyridinium and Imidazolium Substituents

Mata

Avenoza

Busto

et al. 2012

Chemistry A European J

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The reactions of cyclic sulfamidates as electrophiles with a variety of nitrogen-containing aromatic heterocycle nucleophiles, such as pyridines, N-alkylimidazoles and N-methylbenzimidazol, was explored. In all cases, although the nucleophilic substitution reactions occurred on quaternary centres, elimination products were not detected. The inversion of configuration at this quaternary centre was determined by X-ray diffraction analysis and the enantiomeric excess of the reactions was checked by chiral HPLC. This synthetic approach allowed us to obtain a new family of chiral charged β(2,2)-amino acids, including a new bisamino acid that incorporates an imidazolium salt as a cross-linker. In this context, the treatment of these chiral imidazolium salts with Ag(2)O opens the way to new chiral N-heterocyclic carbenes, which are important substrates in the fields of organometallic and organocatalytic chemistry. Additionally, we have done a thorough conformational analysis of these β-amino acid derivatives, both in the solid state and in solution. The most important conformational feature of these acyclic systems is the rigidity of the N-CH(2)-C-N(+) dihedral angle, which is essentially due to the gauche effect.

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Studies on chemical carcinogens. XXI. Quantitative structure-mutagenicity relationship among substituted styrene oxides.

Cited by 20 publications

References 0 publications

Mutagenicity of para-substituted α-methylstyrene oxide derivatives with Salmonella

Mutagenicity of para-substituted α-methylstyrene oxide derivatives with Salmonella

4‐Oxiranylbenzonitrile 52695‐39‐3

Quaternary Chiral β^2,2‐Amino Acids with Pyridinium and Imidazolium Substituents

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Studies on chemical carcinogens. XXI. Quantitative structure-mutagenicity relationship among substituted styrene oxides.

Cited by 20 publications

References 0 publications

Mutagenicity of para-substituted α-methylstyrene oxide derivatives with Salmonella

Mutagenicity of para-substituted α-methylstyrene oxide derivatives with Salmonella

4‐Oxiranylbenzonitrile 52695‐39‐3

Quaternary Chiral β2,2‐Amino Acids with Pyridinium and Imidazolium Substituents

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Product

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Quaternary Chiral β^2,2‐Amino Acids with Pyridinium and Imidazolium Substituents