SC-58236, SC-236
4-[5-(4-氯苯基)-3-(三氟甲基)吡唑-1-基]苯磺酰胺Chemical Name: 4-[5-(4-Chlorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
CAS No. 170569-86-5, 251972-30-2
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator)
合成路线:Claisen condensation of 4'-chloroacetophenone (I) with ethyl trifluoroacetate in the presence of NaOMe provided diketone (II).Subsequent reaction of (II) with 4-sulfamoylphenylhydrazine (III) provided the title 1,5-diaryl pyrazole along with minor amounts of the 1,3-diaryl regioisomer,which was removed by recrystallization from EtOAc and isooctane.
合成路线:The condensation of 4-methylacetophenone (I) with ethyl trifluoroacetate (II) by means of NaOMe in refluxing methanol gives 4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione,which is cyclized with 4-hydrazinophenylsulfonamide (III) in refluxing ethanol.
📌 参考资料/链接：
参考文献标题:Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635,celecoxib)
文献作者:Penning,T.D.; Bertenshaw,S.R.; Talley,J.J.; Carter,J.S.; Collins,P.W.; Docter,S.; Graneto,M.J.; Lee,L.F.; Malecha,J.W.; Miyashiro,J.M.; Rogers,R.S.; Rogier,D.J.; Yu,S.S.; Anderson,G.D.; Burton,E.G.; Cogburn,J.N.; Gregory,S.A.; et al.
参考来源:J Med Chem 1997,40(9),1347