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Synthesis and Nuclear Magnetic Resonance Spectroscopic, Mass Spectroscopic, and Plasma Amine Oxidase Inhibitory Properties of Analogues of 1‐Methyl‐4‐Phenyl‐1,2,3,6‐Tetrahydropyridine
Author(s) -
Bhatti A. R.,
Burdon J.,
Williams A. C.,
Pall H. S.,
Ramsden D. B.
Publication year - 1988
Publication title -
journal of neurochemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.75
H-Index - 229
eISSN - 1471-4159
pISSN - 0022-3042
DOI - 10.1111/j.1471-4159.1988.tb10578.x
Subject(s) - chemistry , inhibitory postsynaptic potential , amine oxidase , amine gas treating , nuclear magnetic resonance , plasma , stereochemistry , organic chemistry , biology , neuroscience , physics , quantum mechanics
Abstract: Seventeen analogues of l‐methyl‐4‐phenyl‐1,2,3,6‐tetrahydropyridine were synthesized using three reaction pathways: condensation of phenols with 1‐methyl‐4‐piperidone, reaction of Grignard reagents with 1‐methyl‐4‐piperidone followed by dehydration of the product, and aminomethylation of olefins. The identity of the products of synthesis was established by nuclear magnetic resonance spectroscopy, mass spectroscopy. and elemental analysis. Thirteen analogues were shown to inhibit the oxidation of benzylamine by bovine plasma amine oxidase. Increasing the length of the aliphatic chain of N ‐substituted analogues resulted in increased inhibition. In 4‐phenyl‐substituted analogues, both the position and electronic character of the substituent group affected the degree of inhibition.