CAS: 170570-09-9; 4-(5-(2,4-Dimethylphenyl)-3-(Trifluoromethyl)-1H-Pyrazol-1-yl)Benzenesulfonamide (Celecoxib Impurity)

该化合物是一种有选择性的环氧酶-2(COX-2)抑制剂,通过在2点添加一个甲基组从Celecoxib结构上产生,这种改变增强了其药用动力特性,包括改善了代谢稳定性和生物利用率;该复合物具有很强的抗炎作用和止痛作用,同时尽量减少了与非选择性COX抑制有关的肠胃副作用;它选择COX-2大于COX-1,使它成为研究与炎症有关的病症,例如关节炎和慢性疼痛的有价值的候选物;甲基替代物还可能影响紧凑性和半衰期,在治疗应用方面提供潜在优势;适用于临床前研究的2-甲基-丙基氧化物用于调查COX-2调解途径.

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457639-26-8 170569-87-6 170571-01-4

合成工艺路线路线简述

    📜2,4-二甲基苯乙酮置于sodium Methylate体系中,用 甲醇,乙醇 用作溶剂,化学反应 44.0H,反应生成塞来昔布杂质7
    参考文献: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)
    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)
    摘要:A Series Of Sulfonamide-Containing 1,5-Diarylpyrazole Derivatives Were Prepared And Evaluated For Their Ability To Block Cyclooxygenase-2 (Cox-2) In Vitro And In Vivo. Extensive Structure-Activity Relationship (Sar) Work Was Carried Out Within This Series,And A Number Of Potent And Selective Inhibitors Of Cox-2 Were Identified. Since An Early Structural Lead (1F,Sc-236) Exhibited An Unacceptably Long Plasma Half-Life,A Number Of Pyrazole Analogs Containing Potential Metabolic Sites Were Evaluated Further In Vivo In An Effort To Identify Compounds With Acceptable Pharmacokinetic Profiles. This Work Led To The Identification Of Ii (4-[5-(4-Methylphenyl)-3-(Trifluoromethyl)-1H-Pyrazol-1-Yl]Benzenesulfonamide,Sc-58635,Celecoxib),Which Is Currently In Phase Iii Clinical Trials For The Treatment Of Rheumatoid Arthritis And Osteoarthritis.
    Doi:10.1021/jm960803Q

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