Selective COX-2 inhibitors. Part 1: Synthesis and biological evaluation of phenylazobenzenesulfonamides

Wei Jern Tsai, Young Ji Shiao, Shwu Jiuan Lin, Wen Fei Chiou, Lie Chwen Lin, Tsang Hsiung Yang, Che Ming Teng, Tain Shung Wu, Li Ming Yang

研究成果: 雜誌貢獻文章

43 引文 (Scopus)

摘要

A series of phenylazobenzenesulfonamide derivatives were designed and synthesized for the evaluation as selective cyclooxygenase-2 (COX-2) inhibitors in a cellular assay using human whole blood (HWB) and an enzymatic assay using purified ovine enzymes. Extensive structure-activity relationships (SAR) were studied within this series, and several of selective COX-2 inhibitors have been identified. Among them, compound 8, 4-(4-amino-2-methylsulfanyl-phenylazo)benzenesulfonamide, showed a potent inhibitory activity to the cyclooxygenase enzymes (IC50's for COX-1: 23.28 μM; COX-2: 2.04 μM), being active but less COX-2 selective than celecoxib.
原文英語
頁(從 - 到)4440-4443
頁數4
期刊Bioorganic and Medicinal Chemistry Letters
16
發行號17
DOIs
出版狀態已發佈 - 九月 1 2006

指紋

Cyclooxygenase 2 Inhibitors
Celecoxib
Cyclooxygenase 2
Assays
Enzyme Assays
Enzymes
Structure-Activity Relationship
Prostaglandin-Endoperoxide Synthases
Inhibitory Concentration 50
Sheep
Blood
Derivatives
benzenesulfonamide

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

引用此文

Selective COX-2 inhibitors. Part 1 : Synthesis and biological evaluation of phenylazobenzenesulfonamides. / Tsai, Wei Jern; Shiao, Young Ji; Lin, Shwu Jiuan; Chiou, Wen Fei; Lin, Lie Chwen; Yang, Tsang Hsiung; Teng, Che Ming; Wu, Tain Shung; Yang, Li Ming.

於: Bioorganic and Medicinal Chemistry Letters, 卷 16, 編號 17, 01.09.2006, p. 4440-4443.

研究成果: 雜誌貢獻文章

Tsai, Wei Jern ; Shiao, Young Ji ; Lin, Shwu Jiuan ; Chiou, Wen Fei ; Lin, Lie Chwen ; Yang, Tsang Hsiung ; Teng, Che Ming ; Wu, Tain Shung ; Yang, Li Ming. / Selective COX-2 inhibitors. Part 1 : Synthesis and biological evaluation of phenylazobenzenesulfonamides. 於: Bioorganic and Medicinal Chemistry Letters. 2006 ; 卷 16, 編號 17. 頁 4440-4443.
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abstract = "A series of phenylazobenzenesulfonamide derivatives were designed and synthesized for the evaluation as selective cyclooxygenase-2 (COX-2) inhibitors in a cellular assay using human whole blood (HWB) and an enzymatic assay using purified ovine enzymes. Extensive structure-activity relationships (SAR) were studied within this series, and several of selective COX-2 inhibitors have been identified. Among them, compound 8, 4-(4-amino-2-methylsulfanyl-phenylazo)benzenesulfonamide, showed a potent inhibitory activity to the cyclooxygenase enzymes (IC50's for COX-1: 23.28 μM; COX-2: 2.04 μM), being active but less COX-2 selective than celecoxib.",
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author = "Tsai, {Wei Jern} and Shiao, {Young Ji} and Lin, {Shwu Jiuan} and Chiou, {Wen Fei} and Lin, {Lie Chwen} and Yang, {Tsang Hsiung} and Teng, {Che Ming} and Wu, {Tain Shung} and Yang, {Li Ming}",
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T2 - Synthesis and biological evaluation of phenylazobenzenesulfonamides

AU - Tsai, Wei Jern

AU - Shiao, Young Ji

AU - Lin, Shwu Jiuan

AU - Chiou, Wen Fei

AU - Lin, Lie Chwen

AU - Yang, Tsang Hsiung

AU - Teng, Che Ming

AU - Wu, Tain Shung

AU - Yang, Li Ming

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N2 - A series of phenylazobenzenesulfonamide derivatives were designed and synthesized for the evaluation as selective cyclooxygenase-2 (COX-2) inhibitors in a cellular assay using human whole blood (HWB) and an enzymatic assay using purified ovine enzymes. Extensive structure-activity relationships (SAR) were studied within this series, and several of selective COX-2 inhibitors have been identified. Among them, compound 8, 4-(4-amino-2-methylsulfanyl-phenylazo)benzenesulfonamide, showed a potent inhibitory activity to the cyclooxygenase enzymes (IC50's for COX-1: 23.28 μM; COX-2: 2.04 μM), being active but less COX-2 selective than celecoxib.

AB - A series of phenylazobenzenesulfonamide derivatives were designed and synthesized for the evaluation as selective cyclooxygenase-2 (COX-2) inhibitors in a cellular assay using human whole blood (HWB) and an enzymatic assay using purified ovine enzymes. Extensive structure-activity relationships (SAR) were studied within this series, and several of selective COX-2 inhibitors have been identified. Among them, compound 8, 4-(4-amino-2-methylsulfanyl-phenylazo)benzenesulfonamide, showed a potent inhibitory activity to the cyclooxygenase enzymes (IC50's for COX-1: 23.28 μM; COX-2: 2.04 μM), being active but less COX-2 selective than celecoxib.

KW - Anti-inflammatory

KW - Isosterism

KW - Phenylazobenzenesulfonamide

KW - Resveratrol

KW - SAR

KW - Selective COX-2 inhibitors

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