720-94-5Relevant articles and documents
Simple synthesis method of celecoxib
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Paragraph 0021; 0036-0037; 0040-0041; 0044-0045, (2022/03/27)
The invention discloses a simple synthesis method of celecoxib. The method comprises the following steps: taking trifluoroacetoacetate and methylbenzene as starting raw materials, firstly synthesizing a compound I through Friedel-Crafts reaction under the catalysis of aluminum trichloride, and reacting the compound I with p-halobenzene sulfonamide in the presence of hydrazine hydrate under an alkaline condition to obtain celecoxib. The method not only avoids the preparation of the 4-hydrazinobenzenesulfonamide hydrochloride in the traditional method, but also avoids the diazotization reaction step in the production process of the 4-hydrazinobenzenesulfonamide hydrochloride, thereby reducing the risk of industrial production. The method has the advantages of short synthesis steps, one-pot method, simple and easily available raw materials and mild reaction conditions, and is suitable for amplification of chemical production.
In Cellulo Generation of Fluorescent Probes for Live-Cell Imaging of Cylooxygenase-2
Kaur, Jatinder,Bhardwaj, Atul,Wuest, Frank
supporting information, p. 3326 - 3337 (2020/12/09)
Live-cell imaging with fluorescent probes is an essential tool in chemical biology to visualize the dynamics of biological processes in real-time. Intracellular disease biomarker imaging remains a formidable challenge due to the intrinsic limitations of conventional fluorescent probes and the complex nature of cells. This work reports the in cellulo assembly of a fluorescent probe to image cyclooxygenase-2 (COX-2). We developed celecoxib-azide derivative 14, possessing favorable biophysical properties and excellent COX-2 selectivity profile. In cellulo strain-promoted fluorogenic click chemistry of COX-2-engaged compound 14 with non/weakly-fluorescent compounds 11 and 17 formed fluorescent probes 15 and 18 for the detection of COX-2 in living cells. Competitive binding studies, biophysical, and comprehensive computational analyses were used to describe protein-ligand interactions. The reported new chemical toolbox enables precise visualization and tracking of COX-2 in live cells with superior sensitivity in the visible range.
Synthesis, crystal structure and antitumor activity of 3-(2,4-dichlorophenyl)-2-phenyl-5-(p-tolyl)-7-(trifluoromethyl)pyrazolo[1,5-A]pyrimidine
Liu, Jin,Zhao, Juan,Lu, Jiu-Fu
, p. 591 - 596 (2021/02/26)
The title compound, 3-(2,4-dichlorophenyl)-2-phenyl-5-(p-tolyl)- 7-(trifluoromethyl)pyrazolo[1,5-a] pyrimidine (C26H16C12F3N3, Mr = 498.32) has been synthesized by condensation of 4,4,4-trifluoro-1-(p-tolyl)butane- 1,3-dione with 4-(2,4-dichlorophenyl)-3-phenyl-1H-pyrazol-5-amine. The latter was prepared from 2,4-dichlorophenylaceton itrile and ethyl benzoate through Claisen condensation and then cyclization with hydrazine hydrate. The crystal structure of the title compound was determined. In addition, the title compound possesses marked inhibition against the proliferation of human lung adenocarcinoma cell line A549 and human gastric cancer cell line MKN45, displaying promising anticancer activities.