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.
Stevens rearrangement of unsaturated ammonium salts. Synthesis of substituted furans
Manukyan,Sahakyan,Gyulnazaryan, A. Kh.,Babakhanyan,Minasyan,Barseghyan
, (2016)
Ammonium salts bearing but-2-ynyl and phenacyl or 2-(naphth-2-yl)-2-oxoethyl moieties at the nitrogen atom underwent Stevens rearrangement to form substituted furan-3-amines. Quaternization of the latter afforded appropriate iodomethylates.
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.
Preparation method of dinotefuran
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Paragraph 0013; 0048-0053, (2021/08/07)
The invention provides a preparation method of dinotefuran, and belongs to the field of organic synthesis. The invention provides a preparation method of dinotefuran, which is characterized by comprising the following steps: step 1, adding a compound I, a compound II and a solvent into a reaction container, heating to 50 DEG C which is the reflux temperature of the solvent, reacting for 1-24 hours, then adding tetrahydrofuran-3-methylamine, and continuously reacting for 1-24 hours to obtain a reaction solution; and 2, cooling the reaction solution to 0-20 DEG C, standing, filtering, separating the solid and filtrate, and purifying the solid to obtain dinotefuran, wherein the structural formula of the compound I is shown in the specification, the structural formula of the compound II is shown in the specification, and R1 and R2 are independently selected from any one of H, C1-C5 alkyl and C1-C5 alkyl substituted by at least one halogen atom. According to the invention, a brand new dinotefuran synthesis route is developed, the synthesis route is greatly shortened, and the production efficiency is improved.
GLYCOPEPTIDE COMPOUNDS, METHODS FOR PRODUCING THE SAME, AND USES THEREOF
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Paragraph 0169-0170, (2020/12/14)
Disclosed herein are novel compounds and uses thereof. The present compounds are useful in suppressing the growth of various bacteria, including gram-positive and gram-negative bacteria. Accordingly, these compounds may be used to manufacture a medicament or pharmaceutic composition for treating disease and/or disorders associated with bacterial infection, especially antibiotic-resistant bacterial infection. Al so disclosed herein are methods for treating infectious diseases by use of the present compounds, medicament or pharmaceutical composition.
Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium
Tomanová, Monika,Jedinák, Luká?,Canka?, Petr
supporting information, p. 2621 - 2628 (2019/06/03)
Prototropic tautomerism was used as a tool for the reductive dehalogenation of (hetero)aryl bromides and iodides, or dehalogenative sulfonation of (hetero)aryl chlorides and fluorides, using sodium sulfite as the sole reagent in an aqueous medium. This protocol does not require a metal or phase transfer catalyst and avoids using organic solvent as the reaction medium. This method is especially suitable for substrates that readily tautomerize (such as 2-or 4-halogenated aminophenols and 4-halogenated resorcinols), for which dehalogenation or sulfonation proceeds under mild reaction conditions (≤60 °C). As sodium sulfite is an inexpensive, safe, and environmentally less hazardous reagent, this method has at least three potential applications: (i) in the deprotection of halogens as protecting groups, using sodium sulfite as a reducing agent; (ii) in the sulfonation of aromatic halides under mild reaction conditions avoiding hazardous and corrosive reagents/solvents; and (iii) in the transformation of toxic halogenated aromatics into less harmful compounds.
Rhodium(iii)-catalyzed unreactive C(sp3)-H alkenylation of N-alkyl-1H-pyrazoles with alkynes
Li, Tongyu,Liu, Chang,Wu, Shaonan,Chen, Chen C.,Zhu, Bolin
supporting information, p. 7679 - 7683 (2019/08/30)
The first example of pyrazole-directed rhodium(iii)-catalyzed unreactive C(sp3)-H alkenylation with alkynes has been described, which showed a relatively broad substrate scope with good functional group compatibility. Moreover, we demonstrated that the transitive coordinating center pyrazole could be easily removed under mild conditions.
Industrial production method for pyrazole
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Paragraph 0032; 0033; 0034; 0035; 0036; 0037; 0038-0051, (2017/08/27)
The invention relates to an industrial production method for pyrazole and belongs to the technical field of preparation of pyrazole. The industrial production method for pyrazole, disclosed by the invention, comprises the steps of dropwise adding sulfuric acid into a mixture solution of glycerine and hydrazine hydrate, carrying out a one-step reaction to synthesize a crude pyrazole product, then, using ammonia to neutralize excessive sulfuric acid and absorb sulfur dioxide produced from the reaction, and subjecting the crude pyrazole product to aftertreatment, thereby obtaining a refined pyrazole product. The industrial production method is simple in operation, low in cost and high in yield and is energy-saving and environmentally friendly, the chromaticity of the product is improved, and the quality of the product is improved, so that the method is applicable to large-scale industrial production and automated production.
Versatile Tri(pyrazolyl)phosphanes as Phosphorus Precursors for the Synthesis of Highly Emitting InP/ZnS Quantum Dots
Panzer, René,Guhrenz, Chris,Haubold, Danny,Hübner, René,Gaponik, Nikolai,Eychmüller, Alexander,Weigand, Jan J.
supporting information, p. 14737 - 14742 (2017/10/23)
Tri(pyrazolyl)phosphanes (5R1,R2) are utilized as an alternative, cheap and low-toxic phosphorus source for the convenient synthesis of InP/ZnS quantum dots (QDs). From these precursors, remarkably long-term stable stock solutions (>6 months) of P(OLA)3 (OLAH=oleylamine) are generated from which the respective pyrazoles are conveniently recovered. P(OLA)3 acts simultaneously as phosphorus source and reducing agent in the synthesis of highly emitting InP/ZnS core/shell QDs. These QDs are characterized by a spectral range between 530–620 nm and photoluminescence quantum yields (PL QYs) between 51–62 %. A proof-of-concept white light-emitting diode (LED) applying the InP/ZnS QDs as a color-conversion layer was built to demonstrate their applicability and processibility.
