Synthesis and in vitro biological evaluation of fluoro-substituted-4-phenyl-1,2,3,6-tetrahydropyridines as monoamine oxidase B substrates.
The substrate properties of three beta-fluoro-4-phenyl-1,2,3,6-tetrahydropyridines related to the proneurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine have been examined in an effort to evaluate the contribution of electronic parameters to the MAO-B catalyzed allylic-alpha-carbon oxidation of the tetrahydropyridinyl system. The design, synthesis, and biological evaluation of these analogues are presented and correlations to amine ionization potentials versus substrate activity are discussed.
Beeler
Aaron B
AB
Department of Medicinal Chemistry and Laboratory for Applied Drug Design and Synthesis, University of Mississippi, University MS 38677, USA.
Gadepalli
Rama Sarma V S
RS
Steyn
Salome
S
Castagnoli
Neal
N
Rimoldi
John M
JM
D004353:Drug Evaluation, Preclinical; D009682:Magnetic Resonance Spectroscopy; D008995:Monoamine Oxidase / Q000378:metabolism*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D013379:Substrate Specificity
D011725:Pyridines; D008995:Monoamine Oxidase