921617-76-7Relevant articles and documents
Primary Sulfonamide Functionalization via Sulfonyl Pyrroles: Seeing the N?Ts Bond in a Different Light
Ozaki, Tomoya,Yorimitsu, Hideki,Perry, Gregory J. P.
supporting information, p. 15387 - 15391 (2021/10/04)
Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy-to-access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation.
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.
Preparation method of celecoxib genotoxic impurity
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Paragraph 0013; 0020-0021; 0024-0025; 0028-0029; 0032-0033, (2020/05/01)
The invention provides a preparation method of a celecoxib genotoxic impurity. The method comprises the following steps: step 1, cyclizing G1 and G2 to generate G3; step 2, carrying out sulfonylationon the G3 to obtain G4; 3, generating G5 by the G4, name
NHC-Catalyzed Deamination of Primary Sulfonamides: A Platform for Late-Stage Functionalization
Fier, Patrick S.,Maloney, Kevin M.
supporting information, p. 1441 - 1445 (2019/01/30)
Herein we describe the development and application of a method for the mild, late-stage conversion of primary sulfonamides to several other other functional groups. These reactions occur via initial reductive deamination of sulfonamides to sulfinates via an NHC-catalyzed reaction of transiently formed N-sulfonylimines. The method described here is tolerant of nearly all common functional groups, as exemplified by the late-stage derivatization of several complex pharmaceutical compounds. On the basis of the prevalence of sulfonamide-containing drugs and building blocks, we have developed a method to enable sulfonamides to be applied as versatile synthetic handles for synthetic chemsitry.
New celecoxib derivatives as anti-inflammatory agents
Szabó, Gy?rgy,Fischer, János,Kis-Varga, ágnes,Gyires, Klára
, p. 142 - 147 (2008/09/19)
A series of 1,5-diarylpyrazoles with a substituted benzenesulfonamide moiety was synthesized and evaluated for cyclooxygenase (COX-1/COX-2) inhibitory activities. Some compounds, for example, (±)-2-[4-(5-p-tolyl-3- trifluoromethyl-pyrazole-1-yl)-benzenesulfonylaminooxy]-propionic acid 16 and its disodium salt 21, had a higher in vivo anti-inflammatory activity compared to celecoxib, despite having no in vitro COX-1 or COX-2 inhibitory activity. Their gastrointestinal side effect profile is essentially more favorable than that of celecoxib.
NEW 1 , 2 -DIARYL PYRAZOLES USEFUL AS ANALGETIC AND ANTI-INFLAMMATORY AGENTS
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Page/Page column 15, (2008/06/13)
The present invention relates to new compounds of formula (I), (I) wherein the meaning of R1 is hydrogen atom, C1-C5 acyl group, benzoyl group or R2- COOR3 group, Y is hydrogen atom or alkali ion, R2 is C1-C4 straight or branched alkylidene group and R3 is hydrogen atom, C1-C4 alkyl group or alkali ion, and/or stereoisomers and/or diastereomers and/or pharmaceutically acceptable salts and/or hydrates and/or solvates thereof, which are suitable for the treatment of pain of acute and chronic inflammation origin as well as postoperative pain and dysmenorrhea. The invention also relates to the process of the synthesis of compounds of formula (I) as well as the pharmaceutical composition containing the same and the use for treatment of pain, inflammation and disorders associated with inflammation.
