3469-69-0Relevant articles and documents
4-Phosphopyrazol-2-yl alanine: A non-hydrolysable analogue of phosphohistidine
Lilley, Matthew,Mambwe, Bezaleel,Thompson, Mark J.,Jackson, Richard F. W.,Muimo, Richmond
, p. 7305 - 7308 (2015)
We report the synthesis of a stable analogue of τ-phosphohistidine: 4-phosphopyrazol-2-yl alanine (pPza). Polyclonal antibodies generated against the mimic show high reactivity and selectivity for τ-phosphohistidine, with minor or no cross-reactivity towards non-phosphorylated histidine or O-phosphoamino acids, including phosphotyrosine.
Cytotoxic Ruthenium(II) Complexes of Pyrazolylbenzimidazole Ligands That Inhibit VEGFR2 Phosphorylation
Acharya, Moulinath,Chakraborty, Ayan,Chakraborty, Manas Pratim,Das, Rahul,Koley, Tuhin Subhra,Mukherjee, Arindam,Purkait, Kallol,Roy, Shantanu Saha,Roy, Souryadip
supporting information, p. 18379 - 18394 (2021/12/01)
Eight new ruthenium(II) complexes of N,N-chelating pyrazolylbenzimidazole ligands of the general formula [RuII(p-cym)(L)X]+ [where the ligand L is 2-(1H-pyrazol-1-yl)-1H-benzo[d]imidazole (L1) substituted at the 4 position of the pyrazole ring by Cl (L2), Br (L3), or I (L4) and X = Cl- and I-] were synthesized and characterized using various analytical techniques. Complexes 1 and 3 were also characterized by single-crystal X-ray crystallography, and they crystallized as a monoclinic crystal system in space groups P21/n and P21/c, respectively. The complexes display good solution stability at physiological pH 7.4. The iodido-coordinated pyrazolylbenzimidazole ruthenium(II) p-cymene complexes (2, 4, 6, and 8) are more resistant toward hydrolysis and have less tendency to form monoaquated complexes in comparison to their chlorido analogues (1, 3, 5, and 7). The halido-substituted 2-(1H-pyrazol-1-yl)-1H-benzo[d]imidazole ligands, designed as organic-directing molecules, inhibit vascular endothelial growth factor receptor 2 (VEGFR2) phosphorylation. In addition, the ruthenium(II) complexes display a potential to bind to DNA bases. The cytotoxicity profile of the complexes (IC50 ca. 9-12 μM for 4-8) against the triple-negative breast cancer cells (MDA-MB-231) show that most of the complexes are efficient. The lipophilicity and cellular accumulation data of the complexes show a good correlation with the cytotoxicity profile of 1-8. The representative complexes 3 and 7 demonstrate the capability of arresting the cell cycle in the G2/M phase and induce apoptosis. The inhibition of VEGFR2 phosphorylation with the representative ligands L2 and L4 and the corresponding metal complexes 3 and 7 in vitro shows that the organic-directing ligands and their complexes inhibit VEGFR2 phosphorylation. Besides, L2, L4, 3, and 7 inhibit the phosphorylation of extracellular signal-regulated kinase 1/2 (ERK1/2) and proto-oncogene tyrosine-protein kinase (Src), capable of acting downstream of VEGFR2 as well as independently. Compounds L2, L4, 3, and 7 have a lesser effect on ERK1/2 and more prominently affect Src phosphorylation. We extended the study for L2 and 3 in the Tg(fli1:gfp) zebrafish model and found that L2 is more effective in vivo compared to 3 in inhibiting angiogenesis.
Method for synthesizing 1 - methyl -4 -iodo pyrazole (by machine translation)
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Paragraph 0050-0053, (2020/06/16)
The invention relates to the technical field 1 - methyl -4 - iodinol synthesis, in particular to a synthesis method of 1 - methyl -4 - iodo pyrazole. The synthesis method of 1 - methyl -4 - iodinol comprises the following steps: (1) mixing 1 - methylpyrazole with iodine, heating to 40 - 80 °C, dropwise adding an oxidizing agent aqueous solution to carry out iodination reaction, and (2) adding alkali liquor to 5 - 9 DEG C to obtain a light yellow crystal, namely 1 - methyl -4 - iodo pyrazole. To 1 - methyl -4 - iodinol synthesis method, 1 - methylpyrazole raw materials are used as the iodinating agent, and an oxidizing agent, an oxidizing agent and hydrogen iodide are added to generate iodine, so that iodine is fully utilized, the reaction rate and product yield are improved, and the synthesis cost 1 - methyl -4 -iodo pyrazole is greatly reduced. (by machine translation)
Deprotonation of 4-ethynylpyrazolium salts
Ahlburg, Nils Lennart,Doppleb, Olivia,Hillrichs, Kai,Namyslo, Jan C.,Hübner, Eike G.,Schmidt, Andreas
, p. 1203 - 1215 (2018/08/06)
4-Ethynyl-1,2-dimethylpyrazolium salts were prepared by methylation of the corresponding 4-ethynyl-1-methylpyrazoles with trimethyloxonium tetrafluoroborate and were deprotonated to give the corresponding pyrazolium-4acetylenides, which are mesomeric betaines. These can be represented as alkynyl- or mesoionic allenylidene-type resonance forms. Calculations and spectroscopic investigations were performed to determine the contribution of each canonical form to the overall structure. Ylides and N-heterocyclic carbenes are tautomers of the betaines. Their relative stabilities have been compared.
