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Xenobiotica
the fate of foreign compounds in biological systems
Volume 16, 1986 - Issue 6
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Original Article

Metabolic N-Hydroxylation of substituted acetophenone ixnines. I. Evidence for formation of isomeric oximes

J. W. Gorrod Chelsea Department of Pharmacy, Kings College London (KQC), University of London, Manresa Road, Chelsea, London, SW3 6LX, UK
&
M. Christou Chelsea Department of Pharmacy, Kings College London (KQC), University of London, Manresa Road, Chelsea, London, SW3 6LX, UK; Department of Pharmacology, Medical Sciences Center, University of Wisconsin Medical School, Madison, WI, 53706, USA
Pages 575-585 | Received 12 Jul 1985, Published online: 30 Sep 2009

References

  • Clarke H.T., Read R.R. Organic Synthesis. John Wiley, New York 1933; Vol. 1: 514–520, Collective
  • Clement B. The N-oxidation of benzamidines in vitro. Xenobiotica 1983; 13: 467–473
  • Cowan D.A., Christou M., Gorrod J.W. 1986, Submitted to Biomed. Mass spectrom
  • Dignam K.J., Hegarty A.F., Begley M.J. Reaction of 1,3-dipoles in aqueous solution. 5. Structural studies on isolable (E) and (Z)-NN-disubstituted amidoximes. Crystal and molecular structure of (E)-morpholino-p-nitrobenzamidoxime. Journal of the Chemical Society; Perkin Transactions 1980; II: 704–709
  • Goldstein A., Aronow L., Kalman S.M. Principles of Drug Action. Harper and Row, New York 1969; 398–342
  • Gorrod J.W. Differentiation of various types of biological oxidation of nitrogen in organic compounds. Chemico-Biological Interactions 1973; 7: 289–303
  • Gorrod J.W., Temple D.J., Beckett A.H. The metabolism of N-ethyl-N-methylaniline by rabbit liver microsomes: The measurement of metabolites by gas-liquid chromatography. Xenobiotica 1975; 5: 453–463
  • Gorrod J.W., Christou M. Enzyme characteristics of imine N-hydroxylation. Biological Reactive Intermediates II—part B, R. Synder, D.V. Parke, J.J. Kocsin, D.J. Jollow, G.G. Gibson, C.M. Witmer. Plenum, New York 1982a; 1133–1142
  • Gorrod J.W., Christou M. Isomeric oximes as in vitro metabolites of acetophenone imines. Microtomes, Drug Oxidations and Drug Toxicity, R. Sato, R. Kato. Japanese Scientific Society, Tokyo 1982b; 563–564
  • Hauser C.R., Hoffenberg D.S. Formation of certain mesityl ketoximes from ketimines. Beckmann rearrangements. Journal of the American Chemical Society 1955; 77: 4885–4887
  • Hucker H.B., Michniewicz B.M., Rhodes R.E. Phenylacetone oxime. An intermediate in the oxidative deamination of amphetamine. Biochemical Pharmacology 1971; 20: 2123–2128
  • IUPAC, 1970. Tentative rules for nomenclature of organic chemistry. Section E, Fundamental Stereochemistry. Journal of Organic Chemistry 1968; 35: 2849–2867
  • Lotlikar P.D., Enamoto M., Miller J.A., Miller E.C. Species variation in the N- and ring-hydroxylation of 2-acetylaminofluorene and effects of 3-methylcholanthrene pre-treatment. Proceedings of the Society for Experimental Biology and Medicine 1967; 125: 341–346
  • Lowry O.H., Rosebrough NT.J., Farr L.A., Randall R.J. Protein measurement with the folin phenol reagent. Journal of Biological Chemistry 1951; 193: 265–275
  • Lustig E. A nuclear magnetic resonance study of syn-anti isomerism in ketoximes. Journal of Physical Chemistry 1961; 65: 491–495
  • Moureau C., Mignonac G. Les cétimines. Annales de Chimie (Paris) 1920; 14: 322–359
  • Murphy P.J. Enzymatic oxidation of nicotine to nicotine $DL1′(5′) minimum ion. A newly discovered intermediate in the metabolism of nicotine. Journal of Biological Chemistry 1973; 248: 2796–2800
  • Omura T., Sato R. A new cytochrome in liver microsomes. Journal of Biological Chemistrv 1962; 237: 1375–1376
  • Parli C.J., Wang N.L., McMahon R.E. Mechanism of the oxidation of d-amphetamine by rabbit liver oxygenase-Oxygen-18 studies. Biochemical and Biophysical Research Communications 1971a; 43: 1204–1209
  • Parli C.J., Wang N.L., McMahon R.E. The enzymatic N-hydroxylation of an imine. A new cytochrome P-450-dependent reaction catalyzed by hepatic microsomal monooxygenases. Journal of Biological Chemistry 1971b; 246: 6953–6955
  • Pearson D.E., Keaton O.D. Lethargic reactions. I The preparation of hindered oximes. Journal of Organic Chemistry 1963; 28: 1557–1558
  • Pickard P.L., Tolbert T.L. An improved method of ketimine synthesis. Journal of Organic Chemistry 1961; 26: 4886–4888
  • Schwartz M.A., Postma E., Kolis S.J., Leon A.S. Metabolites of bromazepam, a benzodiazepine, in the human, dog, rat and mouse. Journal of Pharmaceutical Sciences 1973; 62: 1776–1779
  • Timms G.H., Wildsmith E. Reduction of oximes with tervalent titanium, a mild deoximation procedure and the partial synthesis of eryihromycyclamine. Tetrahedron Letters 1971; 2: 195–198
  • Vogel A.I. A Textbook of Practical Organic Chemistry, 3rd ed. Longmans, London 1957
  • Wittig G. Oxime. Charakteristik und Zahl der Oxime-isomeren. Stereochimie. Akademische Verlagsgesellschaft, M.B.H., Leipzig 1930; 182–200

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