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

Research output: Contribution to journalArticle

43 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4440-4443
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume16
Issue number17
DOIs
Publication statusPublished - Sep 1 2006

Fingerprint

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

Keywords

  • Anti-inflammatory
  • Isosterism
  • Phenylazobenzenesulfonamide
  • Resveratrol
  • SAR
  • Selective COX-2 inhibitors

ASJC Scopus subject areas

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

Cite this

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.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 16, No. 17, 01.09.2006, p. 4440-4443.

Research output: Contribution to journalArticle

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. In: Bioorganic and Medicinal Chemistry Letters. 2006 ; Vol. 16, No. 17. pp. 4440-4443.
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AU - Lin, Lie Chwen

AU - Yang, Tsang Hsiung

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