35344-95-7Relevant academic research and scientific papers
Polymorphs of a pyrazole nitronyl nitroxide and its complexes with metal(ii) hexafluoroacetylacetonates
Catala, Laure,Wurst, Klaus,Amabilino, David B.,Veciana, Jaume
, p. 2736 - 2745 (2006)
The synthesis of pyrazol-4-yl nitronyl nitroxide is reported, along with the crystal structures of its polymorphs and coordination compounds with nickel(ii) and cobalt(ii) hexafluoroacetylacetonate. The polymorphic forms of the pure radical show very different magnetic properties: the alpha form shows only antiferromagnetic interactions while those of the beta form reveal competing ferro- and anti-ferromagnetic interactions. This phenomenon can be traced to the relative orientations of the spin carriers in the crystal. These, in turn, are determined in large measure by the hydrogen bonding networks, where a competition between [N-H...O] and [N-H...N] hydrogen bonds is observed. This delicate balance is also seen in the coordination chemistry of the radical acting as a ligand for the hexafluoroacetylacetonate complexes of nickel(ii) and cobalt(ii). In the former, a 2 1 radical metal complex is formed because of coordination of the pyrazolyl nitrogen atom only. In the latter, a cyclic dimer is formed which involves both the nitrogen and oxygen as coordinating atoms. In both cases, the NH groups of the pyrazolyl moiety lead to the formation of hydrogen bonded networks in the crystals. The magnetic properties of the complexes reveal antiferromagnetic interactions. However, the pyrazolyl nitronyl nitroxide has been proven an interesting component for the formation of coordination compounds with hydrogen bonds in between the magnetic components. The Royal Society of Chemistry 2006.
Preparation method of nitrogen unsubstituted-4-formyl pyrazole
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Paragraph 0020; 0021; 0025-0029; 0050; 0051; 0055-0059, (2020/02/14)
The invention relates to a preparation method of nitrogen unsubstituted-4-formyl pyrazole. The preparation method comprises the following steps: taking 4-halogenated pyrazole or a 4-halogenated pyrazole derivative as a raw material; under the action of trifluoroacetic acid, carrying out reaction with 3, 4-dihydro-2H-pyrane to generate 4-halogenated-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole; carrying out lithiation reaction of 4-halogenated-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole and n-butyllithium at a low temperature, adding N, N-dialkyl formamide and other formylation reagents to introduceformyl, hydrolyzing in an acidic aqueous solution to remove protecting groups, and purifying to obtain the nitrogen unsubstituted-4-formyl pyrazole. The nitrogen unsubstituted-4-formyl pyrazole prepared by the preparation method disclosed by the invention is good in biological activity and has wide application in the fields of medicines and pesticides.
CEREBLON BINDERS FOR THE DEGRADATION OF IKAROS
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Page/Page column 318; 319, (2019/10/23)
The present invention provides cereblon binders for the degradation of Ikaros or Aiolos by the ubiquitin proteasome pathway along with their use in therapeutic applications as described herein.
Dearomatization of oxa- or selenadiazolopyridines with neutral nucleophiles as an efficient approach to pharmacologically relevant nitrogen compounds
Starosotnikov, Alexey M.,Shkaev, Dmitry V.,Bastrakov, Maxim A.,Fedyanin, Ivan V.,Shevelev, Svyatoslav A.,Dalinger, Igor L.
, p. 638 - 640 (2018/12/13)
Highly electrophilic 6-nitro-4-azabenzofuroxan and 6-nitro-4-azabenzo[1,2,5]selenadiazole add π-excessive (het)arenes and other neutral nucleophiles at 7-position to give C–C and N–C-bonded adducts, 1,4-dihydropyridines fused with furoxan or selenadiazole ring.
Design, synthesis and biological activities of 2,3-dihydroquinazolin-4(1H)-one derivatives as TRPM2 inhibitors
Zhang, Han,Liu, Huan,Luo, Xiao,Wang, Yuxi,Liu, Yuan,Jin, Hongwei,Liu, Zhenming,Yang, Wei,Yu, Peilin,Zhang, Liangren,Zhang, Lihe
, p. 235 - 252 (2018/05/09)
Transient receptor potential melastatin 2 (TRPM2), a Ca2+-permeable cationic channel, plays critical roles in insulin release, cytokine production, body temperature regulation and cell death as a reactive oxygen species (ROS) and temperature sensor. However, few TRPM2 inhibitors have been reported, especially TRP-subtype selective inhibitors, which hampers the investigation and validation of TRPM2 as a drug target. To discover novel TRPM2 inhibitors, 3D similarity-based virtual screening method was employed, by which 2,3-dihydroquinazolin-4(1H)-one derivative H1 was identified as a TRPM2 inhibitor. A series of novel 2,3-dihydroquinazolin-4(1H)-one derivatives were subsequently synthesized and characterized. Their inhibitory activities against the TRPM2 channel were evaluated by calcium imaging and electrophysiology approaches. Some of the compounds exhibited significant inhibitory activity, especially D9 which showed an IC50 of 3.7 μM against TRPM2 and did not affect the TRPM8 channel. The summarized structure-activity relationship (SAR) provides valuable insights for further development of specific TRPM2 targeted inhibitors.
TRIAZOLOPYRIDINE INHIBITORS OF MYELOPEROXIDASE
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Paragraph 00175, (2017/03/28)
The present invention provides compounds of Formula (I): wherein A is as defined in the specification, and compositions comprising any of such novel compounds. These compounds are myeloperoxidase (MPO) inhibitors and/or eosinophil peroxidase (EPX) inhibitors, which may be used as medicaments.
Application of flow chemistry to the selective reduction of esters to aldehydes
De Munoz, Juan M.,Alcazar, Jesus,De La Hoz, Antonio,Diaz-Ortiz, Angel
supporting information; experimental part, p. 260 - 263 (2012/02/16)
The reduction of esters to aldehydes is an important transformation in organic chemistry and several reducing agents have been described. However, the use of this reaction in medicinal and natural product chemistry is limited due to the instability of the intermediates and the high reactivity of the reaction products. In the current article, the general and selective reduction of esters with diisobutyl-tert-butoxyaluminum hydride in flow is reported. This reagent allows esters to be reduced in the presence of different functional groups, including those considered to be of similar or higher reactivity. Copyright
HETEROARYLAMINO-PHENYLKETONE DERIVATIVES AND THEIR USE AS KINASE INHIBITORS
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Page 36, (2010/02/10)
The present invention relates to compounds that inhibit VEGF receptor tyrosine kinases, especially KDR, pharmaceutical compositions that contain such compounds, methods of treating VEGF receptor kinase-dependent diseases and conditions in mammals using such compounds and composition and methods for their manufacture.
A multifunctional high-spin biradical pyrazolylbipyridine- bisnitronylnitroxide
Zoppellaro, Giorgio,Enkelmann, Volker,Geies, Ahmed,Baumgarten, Martin
, p. 4929 - 4932 (2007/10/03)
(Chemical Equation Presented) Synthesis and UV-vis, IR, and EPR spectroscopic characterizations, together with X-ray structural analysis, of functional nitronyl- and iminonitroxides attached to pyrazolylbipyridine are described. The exchange interactions between the nitronylnitroxides are found to be stronger than for the iminonitroxides. Although the substitution of a pyridine with the pyrazole ring leads to shorter distances and larger dipolar couplings, the exchange interaction is diminished. While compound 1 forms dimers in the solid state, the terpyridine 3 leads to supramolecular π-stacking.
2,6-Bis(pyrazolyl)pyridine functionalised with two nitronylnitroxide and iminonitroxide radicals
Zoppellaro, Giorgio,Geies, Ahmed,Enkelmann, Volker,Baumgarten, Martin
, p. 2367 - 2374 (2007/10/03)
During the last two decades, growing interest in the field of material chemistry has been focused on the synthetic design of organic high-spin molecules for use as novel magnetic materials. Conjugated radicals based on the bis(pyrazolyl)-pyridine core are very attractive in principle, since they per se combine optical, chelating and magnetic properties on a single molecular entity. The functionalisation of this core via the bis(4′-formyl) derivatives with Ullman radicals results in novel functional biradicals, which may further be used for supramolecular architectures. In this paper we describe the synthesis, structure and properties of 2,6-bis[4′-(3-oxo-1-oxyl-4,4,5, 5-tetramethylimidazolin-2-yl)pyrazol-1′-yl]pyridine (Pz2PyNN) and 2,6-bis[4-(1-oxyl-4,4,5,5-tetramethylimidazolin-2-yl)pyrazolyl]pyridine (Pz2PyIN). The two biradicals can clearly be differentiated by UV/Vis, IR and EPR spectroscopy. The optical absorptions of the blue Pz 2PyNN appear around λmax= 610 nm (ε ≈ 1700 M-1 cm-1) while for Pz2PyIN the orange-red colour arises from absorptions at λmax= 468 nm (ε ≈ 1400 M-1 cm-1). A triplet ground state for the bis(nitronylnitroxide) Pz2PyNN with ΔES-T5 ≈ 11.8 ± 4.8 cm-1 can be deduced from the EPR studies because of the increase of the double integrated intensity times temperature at very low temperatures, indicating complete population of the triplet state. For the related bis(iminonitroxide) Pz2PyIN a much smaller (at least one order of magnitude lower) singlet-triplet energy gap with an upper limit of 0.7 cm-1 has been derived (0.7 ≥ ΔES-T ≥ -0.07 cm-1). The new multifunctional biradicals represent the first example of high-spin molecules in the bis(pyrazolyl)pyridine family. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
