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

doi:10.1016/j.bmc.2007.11.033

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 journal › Article › peer-review

26 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 language	English
Pages (from-to)	2697-2706
Number of pages	10
Journal	Bioorganic and Medicinal Chemistry
Volume	16
Issue number	5
DOIs	https://doi.org/10.1016/j.bmc.2007.11.033
Publication status	Published - Mar 1 2008

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

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

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.",

keywords = "Anti-inflammatory, Benzenesulfonamide, Benzylideneamino, Isosterism, Phenyliminomethyl, Resveratrol, SAR, Selective COX-2 inhibitors",

author = "Lin, {Shwu Jiuan} and Tsai, {Wei Jern} and Chiou, {Wen Fei} and Yang, {Tsang Hsiung} and Yang, {Li Ming}",

year = "2008",

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doi = "10.1016/j.bmc.2007.11.033",

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T2 - Synthesis and biological evaluation of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamides

AU - Lin, Shwu Jiuan

AU - Tsai, Wei Jern

AU - Chiou, Wen Fei

AU - Yang, Tsang Hsiung

AU - Yang, Li Ming

PY - 2008/3/1

Y1 - 2008/3/1

N2 - 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.

AB - 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.

KW - Anti-inflammatory

KW - Benzenesulfonamide

KW - Benzylideneamino

KW - Isosterism

KW - Phenyliminomethyl

KW - Resveratrol

KW - SAR

KW - Selective COX-2 inhibitors

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

Abstract

Keywords

ASJC Scopus subject areas

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