The Recognition of a Diarylimine as a Metabonate Produced During Incubation of N-Benzyl-4-chloroaniline with Hepatic Microsomal Preparations

Author:

Ulgen Chian-Ming Low M1,Gorrod J W2

Affiliation:

1. University of Marmara, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 81010 Haydarpasa, Istanbul, Turkey

2. Chelsea Department of Pharmacy, King’s College London, University of London, Manresa Road, London SW3 6LX, UK

Abstract

Abstract Evidence is presented for the formation of N-benzylidene-4-chloroaniline as a metabonate during the metabolism of N-benzyl-4-chloroaniline. Control studies suggest that the diarylimine is formed as a chemical artifact from the debenzylation products (benzaldehyde and 4-chloroaniline). This novel observation indicates a possible pathway to amide formation from N-benzylanilines via diarylimines as intermediates.

Publisher

Oxford University Press (OUP)

Subject

Pharmaceutical Science,Pharmacology

Reference16 articles.

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2. Oxidative N-dealkylation: a Mannich intermediate in the formation of a new metabolite of lidocaine in man;Breck;Science,1971

3. Reduction of Schiff bases. III. Reduction with dimethylamine borane;Billman;J. Org. Chem.,1961

4. Microsomal formation of amides from secondary aromatic amines;Gooderham,1986

5. Microsomal N- and C-oxidation of 4-substituted N-benzylanilines;Gorrod;Xenobiotica,1985

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