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.
Seventeen analogues of 1-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.
Bhatti
A R
AR
Department of Medicine, University of Birmingham, Queen Elizabeth Hospital, England.
Burdon
J
J
Williams
A C
AC
Pall
H S
HS
Ramsden
D B
DB
D015632:1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine; D006631:Amine Oxidase (Copper-Containing); D000818:Animals; D001596:Benzylamines / Q000378:metabolism; D001667:Binding, Competitive; D002417:Cattle; D055598:Chemical Phenomena; D002621:Chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D000587:Oxidoreductases Acting on CH-NH Group Donors / Q000037:antagonists & inhibitors* / Q000097:blood; D011725:Pyridines / Q000138:chemical synthesis / Q000494:pharmacology*
D001596:Benzylamines; D011725:Pyridines; D015632:1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine; C030796:benzylamine; D006631:Amine Oxidase (Copper-Containing); D000587:Oxidoreductases Acting on CH-NH Group Donors