Selective COX-2 inhibitors. Part 2: Synthesis and biological evaluation of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamides

Shwu Jiuan Lin, Wei Jern Tsai, Wen Fei Chiou, Tsang Hsiung Yang, Li Ming Yang

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Two series of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamide derivatives were designed and synthesized for the evaluation as selective cyclooxygenase-2 (COX-2) inhibitors in a cellular assay using human whole blood (HWB). Extensive structure-activity relationships (SAR) were studied within these series. Several compounds were found to be novel and selective COX-2 inhibitors. Among them, the most potent and selective was 4-(3-carboxy-4-hydroxy-benzylideneamino)benzenesulfonamide (20, LA2135), (IC50's for COX-1: 85.13 μM; COX-2: 0.74 μM; SI: 114.5), being more active COX-2 selective than celecoxib.

Original languageEnglish
Pages (from-to)2697-2706
Number of pages10
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number5
DOIs
Publication statusPublished - Mar 1 2008

Fingerprint

Cyclooxygenase 2 Inhibitors
Celecoxib
Cyclooxygenase 2
Structure-Activity Relationship
Inhibitory Concentration 50
Assays
Blood
Derivatives
benzenesulfonamide

Keywords

  • Anti-inflammatory
  • Benzenesulfonamide
  • Benzylideneamino
  • Isosterism
  • Phenyliminomethyl
  • 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 2 : Synthesis and biological evaluation of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamides. / Lin, Shwu Jiuan; Tsai, Wei Jern; Chiou, Wen Fei; Yang, Tsang Hsiung; Yang, Li Ming.

In: Bioorganic and Medicinal Chemistry, Vol. 16, No. 5, 01.03.2008, p. 2697-2706.

Research output: Contribution to journalArticle

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abstract = "Two series of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamide derivatives were designed and synthesized for the evaluation as selective cyclooxygenase-2 (COX-2) inhibitors in a cellular assay using human whole blood (HWB). Extensive structure-activity relationships (SAR) were studied within these series. Several compounds were found to be novel and selective COX-2 inhibitors. Among them, the most potent and selective was 4-(3-carboxy-4-hydroxy-benzylideneamino)benzenesulfonamide (20, LA2135), (IC50's for COX-1: 85.13 μM; COX-2: 0.74 μM; SI: 114.5), being more active COX-2 selective than celecoxib.",
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AU - Yang, Li Ming

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