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.
Neuroprotective effect of novel celecoxib derivatives against spinal cord injury via attenuation of COX-2, oxidative stress, apoptosis and inflammation
An, Yan,Fan, Mingxing,Li, Jianing,Liu, Yajun
, (2020/07/07)
A novel series of celecoxib derivatives were synthesized and evaluated for cyclooxygenase (COX-1/COX-2) inhibitory activities for benefit in spinal cord injury (SCI). The title compounds were synthesized by conventional methods in good yields and subsequently tested for inhibitory activity against COX-1/COX-2. The most potent COX-2 inhibitor among the tested derivatives was further assayed for protective effect against experimental SCI of Sprague-Dawley rats. The designed compounds showed considerable inhibition of COX-2 as compared to COX-1 revealing compound 7m as most potent inhibitor of COX-2 isoenzyme (IC50 = 0.04 μM). The expression of mitochondrial apoptotic genes (Bcl-2 and Bax) together with COX-2 and iNOS was restored near to normal as evidenced by western blot analysis in SCI rats. Taken altogether, compound 7m was identified as most potent inhibitor of COX-2. It also showed protective action against SCI via attenuation of COX-2, oxidative stress and apoptosis and inflammation in Male Sprague-Dawley rats.
