1338596-75-0Relevant academic research and scientific papers
Insight into the functional and structural properties of 3-arylcoumarin as an interesting scaffold in monoamine oxidase B inhibition
Matos, Maria Joao,Vilar, Santiago,Garcia-Morales, Veronica,Tatonetti, Nicholas P.,Uriarte, Eugenio,Santana, Lourdes,Vina, Dolores
, p. 1488 - 1500 (2014/07/21)
The design, synthesis, pharmacological evaluation, and theoretical studies of a new series of halogenated 3-arylcoumarins were carried out with the aim of finding new structural and biological features. This series displays several alkyl, hydroxy, halogen, and/or alkoxy groups in both benzene rings of the 3-arylcoumarin scaffold. Most of the compounds studied show high affinity and selectivity for the human monoamine oxidase B (hMAO-B) isoenzyme, with IC 50 values in the low nanomolar and picomolar range. Most of the evaluated compounds display higher MAO-B inhibitory activity and selectivity than selegiline (the reference compound). Coumarin 12 (3-(3-bromophenyl)-6- methylcoumarin) is the most active compound (IC50=134 pM), being 140-fold more active than selegiline and showing the highest specificity for hMAO-B. To better understand the structure-activity relationships, docking experiments were carried out on human monoamine oxidase (A and B) structures. Finally, the prediction of passive blood-brain partitioning, based on in silico derived physicochemical descriptors, was performed. Coumarins crossing the barrier: The design and synthesis of a new series of halogenated 3-arylcoumarins are described. Monoamine oxidase A and B in vitro inhibition studies, in silico prediction of passive blood-brain partitioning, and docking calculations showed most of the 3-arylcoumarin compounds to be potent and selective.
Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors
Matos, Maria J.,Terán, Carmen,Pérez-Castillo, Yunierkis,Uriarte, Eugenio,Santana, Lourdes,Vi?a, Dolores
, p. 7127 - 7137 (2011/12/04)
New series of 6-substituted-3-arylcoumarins displaying several alkyl, hydroxyl, halogen, and alkoxy groups in the two benzene rings have been designed, synthesized, and evaluated in vitro as human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitors.
