In vitro oxygenation of N,N'-diphenylguanidines

References

• Albert A., Golddacre R., Phillips J. The strength of heterocyclic bases. Journal of the Chemical Society 1948; 2240–2249
   Google Scholar
• Albert A., Serjeant E. P. The Determination of Ionization Constants3rd Edn. Chapman & Hall, London, New York 1984; 70–101
   Google Scholar
• Clement B. The N-oxidation of benzamidines. in vitro. Xenobiotica 1983; 13: 467–463
   PubMed Web of Science ®Google Scholar
• Clement B. In vitro Untersuchungen zur mikrosomalen N-Oxidation N-substituierter Benzamidine. Archiv der Pharmazie 1984; 317: 925–933
   PubMedGoogle Scholar
• Clement B. The biological N-oxidation of amidines and guanidines. Biological Oxidation of Nitrogen in Organic Molecules, J. W. Gorrod, L. A. Damani. Verlag Chemie, Weinheim, Deerfield Beach 1985; 253–266, Chichester: Horwood
   Google Scholar
• Clement B. In vitro Untersuchungen zur mikrosomalen N-oxidation einiger Guanidine. Archiv der Pharmazie 1986; 319: 961–968
   PubMedGoogle Scholar
• Clement B. Structural requirements of microsomal N-oxygenations derived from studies of amidines. Drug Metabolism and Drug Interactions 1989; 7: 87–106
   PubMedGoogle Scholar
• Clement B., KÄMpchen T. 15N-NMR-Studien an 2-Hydroxyguanidinen und Amidoximen. Chemische Berichte 1985; 118: 3481–3491
   Google Scholar
• Clement B., KÄMpchen T. 15N-NMR-Studien der Tautomerie in N-monosubstituierten Amidinen und in N,N'-Diphenylguanidin. Chemische Berichte 1986; 119: 1101–1104
   Google Scholar
• Clement B., Kunze T. Hepatic microsomal N-hydroxylation of adenine to 6-N-hydroxylaminopurine. Biochemical Pharmacology 1990; 39: 925–933
   PubMedGoogle Scholar
• Clement B., Immel M., Pfundner H., Schmitt S., Zimmermann M. New aspects of the microsomal N-hydroxylation of benzamidines. N-Oxidation of Drugs: Biochemistry, Pharmacology, Toxicology, P. Hlavica, L. A. Damani. Chapman & Hall, London 1991; 185–205
   Google Scholar
• Clement B., Zimmermann M. Hepatic microsomal N-demethylation of N-methylbenzamidine: N-dealkylation vs N-oxygenation of amidines. Biochemical Pharmacology 1987a; 36: 3127–3133
   PubMedGoogle Scholar
• Clement B., Zimmermann M. Characteristics of the microsomal N-hydroxylation of benzamidine to benzamidoxime. Xenobiotica 1987b; 17: 659–667
   PubMed Web of Science ®Google Scholar
• Daly J., Jerina D., Witkop B. Migration of deuterium during hydroxylation of aromatic substrates by liver microsomes: I. Influence of ring substituents. Archives of Biochemistry and Biophysics 1968; 128: 517–527
   PubMed Web of Science ®Google Scholar
• Frederick C. B., Hammons G. J., Beland F. A., Yamazoe Y., Guengerich F. P., Zenser T. V., Ziegler D. M., Kadlubar F. F. N-oxidation of primary aromatic amines in relation to chemical carcinogenesis. Biological Oxidation of Nitrogen in Organic Molecules, J. W. Gorrod, L. A. Damani. Verlag Chemie, Weinheim, Deerfield Beach 1985; 131–148, Chichester: Horwood
   Google Scholar
• Gornall A. G., Bardawill C. W., David M. M. Detection of serum proteins. Journal of Biological Chemistry 1949; 177: 751–755
   PubMed Web of Science ®Google Scholar
• Gorrod J. W. Amine-imine tautomerism as a determinant of the site of biological N-oxidation. Biological Oxidation of Nitrogen in Organic Molecules, J. W. Gorrod, L. A. Damani. Verlag Chemie, Weinheim, Deerfield Beach 1985; 219–230, Chichester: Horwood
   Google Scholar
• Guengerich P. G., Macdonald T. L. Chemical mechanisms of catalysis by Cytochromes P-450: a unified view. Accounts in Chemical Research 1984; 17: 9–16
   Web of Science ®Google Scholar
• Hall N. F. The strength of organic bases in glacial acetic acid solution. Journal of the American Chemical Society 1930; 52: 5115–5128
   Google Scholar
• Hanzlik R. P., Hogberg K., Judson C. M. Microsomal hydroxylation of specifically deuterated monosubstituted benzenes. Evidence for direct aromatic hydroxylation. Biochemistry 1984; 23: 3048–3055
   PubMed Web of Science ®Google Scholar
• Jerina D. M., Daly J. W. Arene oxides: a new aspect of drug metabolism. Science 1974; 185: 573–582
   PubMed Web of Science ®Google Scholar
• Kato R. Metabolic activation of mutagenic heterocyclic aromatic amines from protein pyrolysates. Critical Reviews in Toxicology 1986; 16: 307–348
   PubMed Web of Science ®Google Scholar
• Kawata S., Sugiyama Y., Imai Y., Minami Y., Tarui S., Okamoto M., Yamano T. Hepatic microsomal cytochrome P-450-dependent N-demethylation of methylguanidine. Biochemical Pharmacology 1983; 32: 3723–3728
   PubMedGoogle Scholar
• Levy G. C., Lichter R. L. Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy. John Wiley & Sons, New York 1979
   Google Scholar
• Macholdt-Erdniss J. Eine einfache Darstellung aromatischer Guanidine. Berichte der Deutschen Chemischen Gesellschaft 1958; 91: 1992–1995
   Google Scholar
• Meyer R., Sundmacher W. Zur Kenntnis des m-Amidophenols. Berichte der Deutschen Chemischen Gesellschaft 1899; 32: 2112–2124
   Google Scholar
• Otterbacher T., Whitmore F. C. Phenylisothiocyanate and ortho-tolylisothiocyanate as reagents for primary aromatic amines. Journal of the American Chemical Society 1929; 51: 1909–1911
   Google Scholar
• Palmer R. M. J., Ashton D. S., Moncada S. Vascular endothelial cells synthesize nitric oxide from L-arginine. Nature 1988; 333: 664–666
   PubMed Web of Science ®Google Scholar
• Peterson J. A., Prough R. A. Cytochrome P-450 reductase and cytochrome b5 in cytochrome P-450 catalysis. Cytochrome P-450, P. R. Ortiz De Montellano. Plenum Press, New York 1986; 89–118
   Google Scholar
• Poulsen L. L. Organic sulfur substrates for the microsomal flavin-containing monooxygenase. Reviews in Biochemical Toxicology 1981; 3: 33–49
   Google Scholar
• Preston B. D., Miller J. A., Miller E. C. Non-arene oxide aromatic ring hydroxylation of 2,2′,5,5′-tetrachlorobiphenyl as the major metabolic pathway catalyzed by phenobarbital-induced rat liver microsomes. Journal of Biological Chemistry 1983; 258: 8304–8311
   PubMed Web of Science ®Google Scholar
• Rahimtula A. D., O'Brian P. J., Seifried H. E., Jerina D. M. The mechanism of action of cytochrome P-450. Occurrence of the 'NIHshift' during hydroperoxide-dependent aromatic hydroxylations. European Journal of Biochemistry 1978; 89: 133–141
   PubMedGoogle Scholar
• Roth H. J., Kleemann A. Arzneistoffsynthese. Thieme Verlag, Stuttgart, New York 1982; 379
   Google Scholar
• Wilkerson C. J., Greene F. D. Structures of the 1:1:1 adducts of the 'nitroso-isonitrile-isocyanate' reaction. Possible intermediacy of a carbodiimide N-oxide. Journal of Organic Chemistry 1975; 40: 3112–3118
   Google Scholar
• Yamazoe Y., Abu-Zeid M., Manabe S., Toyama S., Kato R. Metabolic activation of a protein pyrolisate promutagen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline by rat liver microsomes and purified cytochrome P-450. Carcinogenesis 1988; 9: 105–109
   PubMed Web of Science ®Google Scholar
• Ziegler D. M. Flavin-containing monooxygenases: catalytic mechanism and substrate specificities. Drug Metabolism Reviews 1988; 19: 1–32
   PubMed Web of Science ®Google Scholar