Synthesis and monoamine oxidase B substrate properties of 1-methyl-4-heteroaryl-1,2,3,6-tetrahydropyridines

Bioorg Med Chem. 1999 Dec;7(12):2835-42. doi: 10.1016/s0968-0896(99)00225-4.

Abstract

Six analogues of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine [MPTP, (1)] bearing various heteroaryl groups at C-4 were synthesized and examined for their monoamine oxidase B substrate properties. The C-4 substituents include the 1-ethylpyrrol-2-yl, 1-propylpyrrol-2-yl, 1-isopropylpyrrol-2-yl, 1-cyclopropylpyrrol-2-yl, 3-ethylfuran-2-yl and 3-ethylthien-2-yl groups. The results provide information concerning steric and polar interactions between the C-4 substituent and the active site of MAO-B that are transmitted to the position of oxidation at C-6 of the tetrahydropyridinyl moiety.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine / analogs & derivatives*
  • 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine / chemical synthesis
  • 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine / metabolism
  • Animals
  • Binding Sites
  • Cattle
  • In Vitro Techniques
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Monoamine Oxidase / metabolism*
  • Oxidation-Reduction
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
  • Monoamine Oxidase