RESUMO
The synthesis and enzyme inhibitor properties of reversible type B monoamine oxidase inhibitors are described. These compounds belong to the 5H-indeno[1,2-c]pyridazine family and possess a hydrophobic benzyloxy or 4,4,4-trifluorobutoxy side chain which, in contrast to a previous assignment, has been unambiguously located at C(8) of the heterocyclic moiety. Investigation of the regioisomeric structures establishes that substitution of the 5H-indeno[1,2-c]pyridazin-5-one core at C(7) vs C(8) dramatically influences the MAO-inhibiting properties of these compounds.
Assuntos
Indenos/síntese química , Inibidores da Monoaminoxidase/síntese química , Piridazinas/síntese química , Cristalografia por Raios X , Humanos , Interações Hidrofóbicas e Hidrofílicas , Técnicas In Vitro , Indenos/química , Indenos/farmacologia , Mitocôndrias Hepáticas/efeitos dos fármacos , Mitocôndrias Hepáticas/enzimologia , Estrutura Molecular , Inibidores da Monoaminoxidase/química , Inibidores da Monoaminoxidase/farmacologia , Piridazinas/química , Piridazinas/farmacologia , Estereoisomerismo , Relação Estrutura-AtividadeRESUMO
Hexyl thiol has been transformed to hexyl selenol and related selenides and selenocyanate by substitution of the corresponding hexyldiphenylsulfonium tetrafluoroborate with selenium nucleophiles.
RESUMO
Complete control of the face of attack in the addition of stannylmetal reagents to γ-alkoxy-α,ß-unsaturated esters can be achieved by using the appropriate counterion (see scheme). The stereochemistry of addition does not depend on the configuration of the C-C double bond, although the stereoselectivity is consistently better with the Z stereoisomer, for which 100 % Si attack is obtained with Li as counterion and 100 % Re attack with LiZnEt2.