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Synthesis and biological evaluation of 4,5-dihydro-1H-pyrazole derivatives as potential nNOS/iNOS selective inhibitors. Part 2: Influence of diverse substituents in both the phenyl moiety and the acyl group.

Abstract：

:In a preliminary article, we reported a series of 4,5-dihydro-1H-pyrazole derivatives as neuronal nitric oxide synthase (nNOS) inhibitors. Here we present the data about the inhibition of inducible nitric oxide synthase (iNOS) of these compounds. In general, we can confirm that these pyrazoles are nNOS selective inhibitors. In addition, taking these compounds as a reference, we have designed and synthesized a series of new derivatives by modification of the heterocycle in 1-position, and by introduction of electron-donating or electron-withdrawing substituents in the aromatic ring. These derivatives have been evaluated as nNOS and iNOS inhibitors in order to identify new compounds with improved activity and selectivity. Compound 3r, with three methoxy electron-donating groups in the phenyl moiety, is the most potent nNOS inhibitor, showing good selectivity nNOS/iNOS.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Carrión MD,Chayah M,Entrena A,López A,Gallo MA,Acuña-Castroviejo D,Camacho ME

doi

10.1016/j.bmc.2013.05.016

subject

Has Abstract

pub_date

2013-07-15 00:00:00

pages

4132-42

issue

14

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)00441-0

journal_volume

21

pub_type

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