RESUMO
Cubylcarbinylamine (1a), (4-cyclopropylcubyl)carbinylamine (1b), and (4-phenylcubyl)carbinylamine (1c) were synthesized and shown to be time-dependent, irreversible inactivators of monoamine oxidase B (MAO B). Substrate protects the enzyme from inactivation, but beta-mercaptoethanol does not, suggesting that these compounds are mechanism-based inactivators. All three compounds were also substrates for MAO B with partition ratios ranging from 152 to 536. The 4-substituted analogues were more potent inactivators than the unsubstituted analogue, indicating a benefit to 4-substitution in this class of inactivators.
Assuntos
Hidrocarbonetos Aromáticos com Pontes/química , Metilaminas/química , Inibidores da Monoaminoxidase/química , Hidrocarbonetos Aromáticos com Pontes/farmacologia , Cinética , Espectroscopia de Ressonância Magnética , Metilaminas/farmacologia , Especificidade por SubstratoRESUMO
[structure: see text] Benzene and 1,2-dichloroethane solutions of the Li(+) salt of the weakly coordinating anion CB(11)Me(12)(-) catalyze the rearrangement of cubane to cuneane, quadricyclane to norbornadiene, basketene to Nenitzescu's hydrocarbon, and diademane to triquinacene. The Claisen rearrangement of phenyl allyl ether is also strongly accelerated.