【药物名称】Celecoxib, YM-177, SC-58635, Onsenal, Solexa, Celebrex, Celebra
化学结构式(Chemical Structure):
参考文献No.27493
标题:Substd. pyrazolyl benzenesulfonamides for the treatment of inflammation
作者:Talley, J.J.; Penning, T.D.; Collins, P.W.; Rogier, D.J. Jr.; Malecha, J.W.; Miyashiro, J.M.; Bertenshaw, S.R.; Khanna, I.K.; Granets, M.J.; Rogers, R.S.; Carter, J.S.; Docter, S.H.; Yu, S.S. (Pharmacia Corp.)
来源:EP 0731795; EP 0922697; EP 0924201; JP 1997506350; JP 2000109466; US 5521207; WO 9515316
合成路线图解说明:

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.

参考文献No.33927
标题:Method of preparing 3-haloalkyl-1H-pyrazoles
作者:Zhi, B.; Newaz, M.; Talley, J.J.; Bertenshaw, S. (Pharmacia Corp.)
来源:WO 9637476
合成路线图解说明:

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.

参考文献No.412128
标题:Celecoxib
作者:Graul, A.; Martel, A.M.; Casta馿r, J.
来源:Drugs Fut 1997,22(7),711
合成路线图解说明:

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.

参考文献No.436180
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)
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.
来源:J Med Chem 1997,40(9),1347
合成路线图解说明:

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.

合成路线图解说明:

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.

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