10010-93-2Relevant articles and documents
Palladium catalyzed addition of arylboronic acid or indole to nitriles: Synthesis of aryl ketones
Das, Tuluma,Chakraborty, Amarnath,Sarkar, Amitabha
, p. 7198 - 7202 (2014)
Aryl ketones can be synthesized conveniently by a palladium catalyzed addition of arylboronic acid to nitriles in aqueous triflic acid. This catalytic system was extended to the addition of unprotected indoles to nitriles under a slightly modified condition to produce 3-acyl indoles in good yields.
3-Substituted pyrazoles and 4-substituted triazoles as inhibitors of human 15-lipoxygenase-1
Pelcman, Benjamin,Sanin, Andrei,Nilsson, Peter,No, Kiyo,Schaal, Wesley,?hrman, Sara,Krog-Jensen, Christian,Forsell, Pontus,Hallberg, Anders,Larhed, Mats,Boesen, Thomas,Kromann, Hasse,Vogensen, Stine Byskov,Groth, Thomas,Claesson, Hans-Erik
, p. 3024 - 3029 (2015)
Investigation of 1N-substituted pyrazole-3-carboxanilides as 15-lipoxygenase-1 (15-LOX-1) inhibitors demonstrated that the 1N-substituent was not essential for activity or selectivity. Additional halogen substituents on the pyrazole ring, however, increased activity. Further development led to triazole-4-carboxanilides and 2-(3-pyrazolyl) benzoxazoles, which are potent and selective 15-LOX-1 inhibitors.
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.
, p. 14737 - 14742 (2017)
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.
New efficient synthetic routes to trifluoromethyl substituted pyrazoles and corresponding β-diketones
Grünebaum, Mariano,Buchheit, Annika,Günther, Christina,Wiemh?fer, Hans-D.
, p. 1555 - 1559 (2016)
An improved and more efficient synthesis procedure for trifluoromethyl substituted pyrazoles, namely 3,5-bis(trifluoromethyl)-1H-pyrazole (1a), 5-(pentafluoroethyl)-3-(trifluoromethyl)-1H-pyrazole (1b), 5-(heptafluoropropyl)-3-(trifluoromethyl)-1H-pyrazol
An efficient synthesis of 1-cyanoacetyl-5-halomethyl-4,5-dihydro-1H- pyrazoles in ionic liquid
Moreira, Dayse N.,Frizzo, Clarissa P.,Longhi, Kelvis,Zanatta, Nilo,Bonacorso, Helio G.,Martins, Marcos A. P.
, p. 1049 - 1054 (2008)
The synthesis of eleven 1-cyanoacetyl-5-hydroxy-5-halomethyl-4,5-dihydro- 1H-pyrazoles from the reaction of 4-alkoxy-3-alken-2-ones f(R 3C(O)C(R2) = C(R1)OR, where R 3 = CF3, CCl3, CHClsub
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Nishiwaki
, p. 885,887 (1967)
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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.