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Journal of Enzyme Inhibition and Medicinal Chemistry Volume 17, 2002 - Issue 6
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Research Article

Derivatization of (±)-5-[(2-Methylphenoxy)methyl]-2-amino-2-oxazoline, an Imidazoline Binding Sites Ligand, with (+)- (R) -α-Methylbenzyl Isocyanate for Drug Monitoring Purposes

Myriam Matoga EA 2962--Pharmacochimie, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux cedex, France
,
Isabelle Forfar EA 2962--Pharmacochimie, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux cedex, France
,
Corinne Chaimbault EA 2962--Pharmacochimie, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux cedex, France
,
Jean Guillon EA 2962--Pharmacochimie, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux cedex, France
,
Fabienne Péhourcq Laboratoire de Pharmacologie, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux cedex, France
,
Jean-Jacques Bosc EA 2962--Pharmacochimie, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux cedex, France
,
Marie-Claire Rettori IRIS, 6 place des Pléiades, 92415 Courbevoie cedex, France
&
Christian Jarry EA 2962--Pharmacochimie, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux cedex, France
 show all
Pages 375-379 | Published online: 30 Sep 2008

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  • Chaimbault, C., Bosc, J.J., Jarry, C., Léger, J.M., MarchandGeneste, N. and Carpy, A. (1999) "Structural and theoretical evidence of the reaction products of ethyl (ethoxymethylene) cyanoacetate with 5-phenoxymethy1-2-amino-2-oxazoline", Journal of Molecular Structure 508,193-205.
  • Bosc, J.J., Jarry, C., Carpy, A., Panconi, E. and Descas, P. (1992) "Synthesis and antidepressant activity of 5-(1-aryl-4-piperazino)methy1-2-amino-2-oxazolines", European Journal of Medicinal Chemistry 27,437-442.
  • Jarry, C., Bosc, J.J., Forfar, I., Renard, P., Scalbert, E. and Guardiola, B. (1995) "Nouvelles 5-(arylmethyl)oxazolines, leur procédé de fabrication et les compositions pharmaceutiques qui les contiennent. EP 402437", Chemical Abstracts 125, 58494, (1996).
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  • Bousquet, P. and Feldman, J. (1999) "Drugs acting on imidazoline receptors: a review of their pharmacology, their use in blood pressure control and their potential interest in cardioprotection", Drugs 58, 799-812.
  • Reid, J.L. (2000) "Rilmenidine", American Journal of Hypertension 13, S106-S111.
  • Van Zwieten, P.A. (1999) "Centrally acting antihypertensive drugs. Present and future", Clinical and Experimental Hypertension 21,859-873.
  • Barot, M., Rettori, M.C., Guardiola-Lemaitre, B., Jarry, C., Le Moal, M and Piazza, P.V. (2000) "Interactions between imidazoline binding sites and dopamine levels in the rat nucleus accumbens", European Journal of Neuroscience 12, 4547-4551.
  • Ulrich, H. (1996) The Chemistry and Technology of Isocyanates (John Wiley & Sons, New York).
  • Chenevier, P., Massias, L., Gueylard, D. and Farinotti, R. (1998) "Determination of ethambutol in plasma by high performance liquid chromatography after pre-column derivatization", Journal of Chromatography B 708, 310-315.
  • Kleidernigg, O.P. and Lindner, W. (1998) "Indirect separation of chiral proteinogenic a-amino acids using the fluorescence active (1R,2R)-N-][(2-isothiocyanato)cyclohexyl]-6-methoxy-4-quinolinylamide] as chiral derivatizing agent A comparison", Journal of Chromatography A 795, 251-261.
  • Peter, M., Péter, A. and Fülöp, F. (2000) "Application of (1S,2S)- and (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)-2propylisothiocyanate to the indirect enantioseparation of racemic proteinogenic amino acids", Journal of Chromatography A 871,115-126.
  • Bosc, J.J., Jarry, C., Ouhabi, J., Laguerre, M. and Carpy, A. (1996) "New investigation of the reaction of 2-amino-2oxazolines with isocyanates and isothiocyanates. Evidence of a transposition during the second step", Canadian Journal of Chemistry 74,1341-1347.
  • Ouhabi, J., Jarry, C., Zouanate, A. and Carpy, A. (1997) "2-Amino-2-oxazolines. Part VIII. Calculated molecular properties of tautomeric species", Archiv der Pharmazie 330, 367-371.
  • Bourgeois, G.L., Jarry, C. and Golse, R.F. (1987) "Derivatization of 2-amino-2-oxazolines with trimethylanilinium hydroxyde. Determination of reaction products by gas chromatography-mass spectrometry", Journal of Chromatography 387,442-446.
  • Avalos, M., Babiano, R., Cintas, P., Chavero, M.M., Higes, F.J., Jiménez, J.L., Palacios, J.C. and Silvero, G. (2000) "Reactions of 2-amino-2-thiazolines with isocyanates and isothiocyanates. Chemical and computational studies on the regioselectivity, adduct rearrangement and mechanistic pathways", Journal of Organic Chemistry 65,8882-8892.

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