Structure-metabolism relationships of substituted anilines: prediction of N-acetylation and N-oxanilic acid formation using computational chemistry

References

• BALDWIN, M. K. and HUTSON, D. H., 1980, The metabolism of 3- chloro-4-fluoro-aniline in dog and rat. Xenobiotica, 10, 135–144.
   PubMed Web of Science ®Google Scholar
• CUPID, B. C., BEDDELL, C. R., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1996, Quantitative structure-metabolism relationships for substituted benzoates in the rabbit: prediction of urinary excretion of glycine and glucuronide conjugates. Xenobiotica, 26, 157–176.
   PubMed Web of Science ®Google Scholar
• CUPID, B. C., HOLMES, E., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1999, Quantitative structure-metabolism relationships (QSMR) using computational chemistry: pattern recognition analysis and statistical prediction of phase II conjugation reactions of substituted benzoic acids in the rat. Xenobiotica, 29, 27–42.
   PubMed Web of Science ®Google Scholar
• DEWAR, M. J. S., ZOEBISCH, E. G. and STEWART, J. J. P., 1985, The development and use of quantum-mechanical molecular-models. 76. AM1 - a new general purpose molecular-model. Journal of the American Chemical Society, 107, 3902–3909.
   Google Scholar
• EHLHARDT, W. J. and HOWBERT, J. J., 1991, Metabolism and disposition of p- chloroaniline in rat, mouse, and monkey. Drug Metabolism and Disposition, 19, 366–369.
   PubMed Web of Science ®Google Scholar
• FRIES, W., KIESE, M. and LENK, W., 1971, Additional route in the metabolism of Sulphanilamide. Xenobiotica, 1, 241–256.
   PubMedGoogle Scholar
• FUKUI, K., YONEZAWA, T. and SHINGU, H., 1954, Theory of substitution in conjugated molecules. Bulletin of the Chemical Society of Japan, 27, 423–427.
   Google Scholar
• GHAURI, F. Y., BLACKLEDGE, C. A., GLEN, R. C., SwEATMAN, B. C., LINDON, J. C., BEDDELL, C. R., WILSON, I. D. and NICHOLSON, J. K., 1992a, An approach to a metabolic expert system: structure-metabolism relationships for benzoic acids in the rat. In E. Reid and I. D. Wilson (eds), Methodological Surveys in Biochemistry and Analysis (Cambridge: Royal Society of Chemistry), pp. 21–28.
   Google Scholar
• GHAURI, F. Y., BLACKLEDGE, C. A., GLEN, R. C., SwEATMAN, B. C., LINDON, J. C., BEDDELL, C. R., WILSON, I. D. and NICHOLSON, J. K., 1992b, Quantitative structure-metabolism relationships of substituted benzoic acids in the rat. Computational chemistry, NMR spectroscopy and computer pattern recognition studies. Biochemical Pharmacology, 44, 1935–1946.
   PubMed Web of Science ®Google Scholar
• GHOSE, A. K., PRITCHETT, A. and CRIPPEN, G. M., 1988, Atomic physicochemical parameters for 3-dimensional structure directed quantitative structure-activity-relationships. 3. Modelling hydrophobic interactions. Journal of Computational Chemistry, 9, 80–90.
   Web of Science ®Google Scholar
• HOLMES, E., SWEATMAN, B. C., BOLLARD, M., BLACKLEDGE, C. A., BEDDELL, C. R., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1995, Prediction of urinary sulphate and glucuronide excretion of substituted phenols in the rat using quantitative structure-metabolism relationships. Xenobiotica, 25, 1269–1281.
   PubMed Web of Science ®Google Scholar
• HONG, S. K. and RANKIN, G. O., 1998, Biotransformation of 2- chloroaniline in the Fischer 334 rat: identification of urinary metabolites. Xenobiotica, 28, 985–994.
   PubMed Web of Science ®Google Scholar
• HUTSON, D. H., LAKEMAN, S. K. and LOGAN, C. J., 1984, The fate of 4- cyano-N,N-dimethylaniline in rats; a novel involvement of glutathione in the metabolism of aniline. Xenobiotica, 14, 925–934.
   PubMed Web of Science ®Google Scholar
• KAO, J., FAULKNER, J. and BRIDGES, J. W., 1978, Metabolism of aniline in rats, pigs and sheep. Drug Metabolism and Disposition, 6, 549–555.
   PubMed Web of Science ®Google Scholar
• KIER, L. B. and HALL, L. H., 1986, Molecular Connectivity in Structure-Activity Analysis (New York: Wiley).
   Google Scholar
• KIESE, M. and LENK, W., 1969, Oxidation of acetanilides to glycolanilides and oxanilic acids in rabbits. Biochemical Pharmacology, 18, 1325–1333.
   PubMed Web of Science ®Google Scholar
• KLAMT, A. and SCHUURMAN, G., 1993, COSMO - a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. Journal of the Chemical Society, Perkin Transactions II, pp. 799.
   Google Scholar
• SCARFE, G. B., CLAYTON, E., WILSON, I. D. and NICHOLSON, J. K., 2000, Identification and quantification of metabolites of 2,3,5,6-tetrafluoro-4-trifluoromethylaniline in rat urine using 19F nuclear magnetic resonance spectroscopy, high-performance liquid chromatography-nuclear magnetic resonance spectroscopy and high-performance liquid chromatography-mass spectrometry. Journal of Chromatography B, 748, 311–319.
   PubMed Web of Science ®Google Scholar
• SCARFE, G. B., LINDON, J. C., NICHOLSON, J. K., CLAYTON, E., WRIGHT, B., TAYLOR, S. and WILSON, I. D., 2001, The identification of the urinary metabolites of 4-bromoaniline and 4-bromo-[carbonyl-13q-acetanilide in the rat. Xenobiotica, 32, 325–337.
   Google Scholar
• SCARFE, G. B., LINDON, J. C., NICHOLSON, J. K., WRIGHT, B., CLAYTON, E. and WILSON, I. D., 1999c, Investigation of the quantitative metabolic fate and urinary excretion of 3-methy1-4-trifluoromethylaniline and 3 methyl-4-trifluoromethylacetanilide in the rat. Drug Metabolism and Disposition, 27, 1171–1178.
   PubMed Web of Science ®Google Scholar
• SCARFE, G. B., TUGNAIT, M., WILSON, I. D. and NICHOLSON, J. K., 1999b, Studies on the metabolism of 4-fluoroaniline and 4-fluoroacetanilide in the rat: formation of 4-acetamidophenol (paracetamol) and its metabolites via defluorination and N-acetylation. Xenobiotica, 29, 205–216.
   PubMed Web of Science ®Google Scholar
• SCARFE, G. B., WRIGHT, B., CLAYTON, E., TAYLOR, S., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1998, 19F NMR and directly coupled HPLC-NMR-MS investigations into the metabolism of 2-bromo-4-trifluoromethylaniline in the rat: a urinary excretion balance study without the use of radiolabelling. Xenobiotica, 28, 373–388.
   PubMed Web of Science ®Google Scholar
• SCARFE, G. B., WRIGHT, B., CLAYTON, E., TAYLOR, S., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1999a, Quantitative studies on the urinary metabolic fate of 2- chloro-4-trifluoromethylaniline in the rat using 19F NMR spectroscopy and directly coupled HPLC-NMR-MS. Xenobiotica, 29, 77–92.
   PubMed Web of Science ®Google Scholar
• TUGNAIT, M., 1994, Multinuclear magnetic resonance studies on the metabolism of model fluoroaromatic xenobiotics. PhD thesis, University of London.
   Google Scholar
• WILSON, I. D., MACDONALD, C. M., FROMSON, J. M., TROKE, J. A. and HILLBECK, D., 1985, Species differences in the metabolism of 14C-p-trifluoromethylaniline: production of an oxanilic acid as the major metabolite by the rat. Biochemical Pharmacology, 34, 2025–2028.
   PubMed Web of Science ®Google Scholar