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New series of bromo-6-methyl-3-phenylcoumarin derivatives, with bromo atom in both different benzene rings of the skeleton, and with or without different number of methoxy substituent at the 3-phenyl ring, were synthesized. The methoxy substituents were introduced, in this new scaffold, in the
meta and/or
para positions of the 3-phenyl ring. The synthesized compounds
3–
7 were evaluated as MAO-A and B inhibitors.
With the aim to find out the structural features for the MAO inhibitory activity and selectivity, in the present communication we report the synthesis and pharmacological evaluation of a new series of bromo-6-methyl-3-phenylcoumarin derivatives (with bromo atom in both different benzene rings of the skeleton) with and without different number of methoxy substituent at the 3-phenyl ring. The methoxy substituents were introduced, in this new scaffold, in the
meta and/or
para positions of the 3-phenyl ring. The synthesized compounds
3–
7 were evaluated as MAO-A and B inhibitors using
R-(−)-deprenyl (selegiline) and iproniazide as reference inhibitors, showing, most of them, MAO-B inhibitory activities in the low nanomolar range. Compounds
4 (IC
50
=
11.05
nM),
5 (IC
50
=
3.23
nM) and
6 (IC
50
=
7.12
nM) show higher activity than selegiline (IC
50
=
19.60
nM) and higher MAO-B selectivity, with more than 9050-fold, 30,960-fold and 14,045-fold inhibition levels, with respect to the MAO-A isoform.