14575-62-3Relevant academic research and scientific papers
Synthesis and biological evaluation of the 1-arylpyrazole class of σ1 receptor antagonists: Identification of 4-{2-[5-methyl-1- (naphthalen-2-yl)-1H-pyrazol-3-yloxy]ethyl}morpholine (S1RA, E-52862)
Diaz, Jose Luis,Cuberes, Rosa,Berrocal, Joana,Contijoch, Montserrat,Christmann, Ute,Fernandez, Ariadna,Port, Adriana,Holenz, Joerg,Buschmann, Helmut,Serafini, Maria Teresa,Burgueno, Javier,Zamanillo, Daniel,Merlos, Manuel,Vela, Jose Miguel,Almansa, Carmen,Laggner, Christian
, p. 8211 - 8224,14 (2020/09/15)
The synthesis and pharmacological activity of a new series of 1-arylpyrazoles as potent σ1 receptor (σ1R) antagonists are reported. The new compounds were evaluated in vitro in human σ1R and guinea pig σ2 receptor (σ2R) binding assays. The nature of the pyrazole substituents was crucial for activity, and a basic amine was shown to be necessary, in accordance with known receptor pharmacophores. A wide variety of amines and spacer lengths between the amino and pyrazole groups were tolerated, but only the ethylenoxy spacer and small cyclic amines provided compounds with sufficient selectivity for σ1R vs σ2R. The most selective compounds were further profiled, and compound 28, 4-{2-[5-methyl-1- (naphthalen-2-yl)-1H-pyrazol-3-yloxy]ethyl}morpholine (S1RA, E-52862), which showed high activity in the mouse capsaicin model of neurogenic pain, emerged as the most interesting candidate. In addition, compound 28 exerted dose-dependent antinociceptive effects in several neuropathic pain models. This, together with its good physicochemical, safety, and ADME properties, led compound 28 to be selected as clinical candidate.
Alkoxypyrazoles and the process for their preparation
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Page/Page column 48-49; 55, (2010/03/02)
The present invention relates to a alkoxypyrazoles preparation process, and new alkoxypyrazole compounds.
4-Arylation of 3-alkoxypyrazoles
Guillou, Sandrine,Nesmes, Olivier,Ermolenko, Mikhail S.,Janin, Yves L.
experimental part, p. 3529 - 3535 (2009/09/05)
Following the study of the alkoxypyrazoles nitrogen's reactivity toward arylation or alkylation reactions, we report here our results on the introduction of various aryl groups on carbon 4 position of 3-alkoxypyrazoles. This was achieved from the correspo
A study of the effect of steric hindrance in metal coordination with azo-3-pyrazolones
Snavely, Fred A.,Sweigart, Dwight A.,Yoder, Claude H.,Terzis, Aristides
, p. 1831 - 1834 (2007/10/09)
The formation constants of divalent metal ions with azo derivatives of 1-phenyl-5-methyl-3-pyrazolone have been measured in 75 vol. % dioxane. These azo derivatives are both stronger acids and stronger coordinating ligands than the analogous azo derivatives of 1-phenyl-3-methyl-5-pyrazolone. A steric effect is found with the ortho-substituted derivatives which decreases in the order : I > Br > Cl > F > H and C2H5 > CH3. A possible explanation given is that the ortho groups hinder the retention of water molecules to form MCh2·2H2O in solution (Ch = chelate).
