288-13-1Relevant articles and documents
Copper (II) complexes with novel Schiff-based ligands: synthesis, crystal structure, thermal (TGA–DSC/FT-IR), spectroscopic (FT-IR, UV-Vis) and theoretical studies
Moreira, Jeniffer Meyer,Campos, Guilherme Fava,de Campos Pinto, Leandro Moreira,Martins, Gabriel Rodrigues,Tirloni, Bárbara,Schwalm, Cristiane Storck,de Carvalho, Cláudio Teodoro
, p. 4087 - 4098 (2022)
This study aimed to synthesize two novel Schiff-base ligands through the condensation between N-(2-aminoethyl)pyrazoles and 2-hydroxy-1-naphthaldehyde, which are: NaphPz ((E)-1-(((2-(1H-pyrazol-1-yl)ethyl)imino)methyl)naphthalen-2-ol)) and NaphDPz ((E)-1-(((2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)imino)methyl)naphthalen-2-ol). These novel pyrazole-imines were synthesized, characterized and used as copper (II) ion complexing agents. Different synthetic routes have been adapted to obtain the [Cu(NaphPz)Cl], [Cu(NaphDPz)Cl] and [Cu(NaphPz)2] complexes in the solid state, the first two in the crystalline form and the latter as a powder. The minimum metal–ligand stoichiometry for the three complexes was defined by TGA–DSC thermoanalytical data and by single-crystal X-ray diffraction for the crystalline samples which belong to the P21/n space group. The products of the thermal decomposition of the material were also monitored by TGA–DSC/FT-IR in air and N2 atmospheres in order to suggest how thermal decomposition of the organic portion of the complex occurs. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations compared to experimental results (UV-Vis and FT-IR) show a high degree of correlation. From HOMO/LUMO orbitals, the main major charge distributions, responsible for the absorption bands of the complexes, were determined.
Unexpected ring opening of pyrazolines with activated alkynes: synthesis of 1H-pyrazole-4,5-dicarboxylates and chromenopyrazolecarboxylates
Bhimapaka, China Raju,Kolla, Sai Teja,Rayala, Nageswara Rao,Sridhar, Balasubramanian
supporting information, p. 334 - 338 (2022/01/20)
1H-Pyrazole-4,5-dicarboxylates and chromenopyrazole carboxylates were prepared by reacting pyrazolines with activated alkynes under neat conditions without a catalyst. The products were formed via unexpected ring opening of pyrazolines with the elimination of styrene/ethylene. These types of transformations are unknown and the products formed were confirmed using their spectral/analytical data. In addition, the structures of compounds 5e and 5n were confirmed by single-crystal X-ray analysis. Control experiments were conducted to support the proposed reaction mechanism.
Discovery and SAR Evolution of Pyrazole Azabicyclo[3.2.1]octane Sulfonamides as a Novel Class of Non-CovalentN-Acylethanolamine-Hydrolyzing Acid Amidase (NAAA) Inhibitors for Oral Administration
Armirotti, Andrea,Bandiera, Tiziano,Berti, Francesco,Bertorelli, Rosalia,Bertozzi, Fabio,Bertozzi, Sine Mandrup,Bottegoni, Giovanni,Carbone, Anna,Di Fruscia, Paolo,Fiasella, Annalisa,Giacomina, Francesca,Mengatto, Luisa,Nuzzi, Andrea,Ortega, Jose Antonio,Pagliuca, Chiara,Penna, Ilaria,Pizzirani, Daniela,Ponzano, Stefano,Reggiani, Angelo,Romeo, Elisa,Russo, Debora,Summa, Maria,Tarozzo, Glauco,Giampà, Roberta
, p. 13327 - 13355 (2021/09/20)
Inhibition of intracellularN-acylethanolamine-hydrolyzing acid amidase (NAAA) activity is a promising approach to manage the inflammatory response under disabling conditions. In fact, NAAA inhibition preserves endogenous palmitoylethanolamide (PEA) from degradation, thus increasing and prolonging its anti-inflammatory and analgesic efficacy at the inflamed site. In the present work, we report the identification of a potent, systemically available, novel class of NAAA inhibitors, featuring a pyrazole azabicyclo[3.2.1]octane structural core. After an initial screening campaign, a careful structure-activity relationship study led to the discovery ofendo-ethoxymethyl-pyrazinyloxy-8-azabicyclo[3.2.1]octane-pyrazole sulfonamide50(ARN19689), which was found to inhibit human NAAA in the low nanomolar range (IC50= 0.042 μM) with a non-covalent mechanism of action. In light of its favorable biochemical, in vitro and in vivo drug-like profile, sulfonamide50could be regarded as a promising pharmacological tool to be further investigated in the field of inflammatory conditions.