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

doi:10.1016/j.bmcl.2006.06.036

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

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

46 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 language	English
Pages (from-to)	4440-4443
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	16
Issue number	17
DOIs	https://doi.org/10.1016/j.bmcl.2006.06.036
Publication status	Published - 2006 Sept 1

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2006.06.036

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title = "Selective COX-2 inhibitors. Part 1: Synthesis and biological evaluation of phenylazobenzenesulfonamides",

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.",

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}",

note = "Funding Information: We gratefully thank the National Science Council of Republic of China Grants NSC-94-2320-B-077-005 (L.-M.Y.) and NSC-94-2320-B-038-030 (S.-J.L.), and National Research Institute of Chinese Medicine for research funding (Grant NRICM-95-DMC-007). Copyright: Copyright 2008 Elsevier B.V., All rights reserved.",

year = "2006",

month = sep,

day = "1",

doi = "10.1016/j.bmcl.2006.06.036",

language = "English",

volume = "16",

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T1 - Selective COX-2 inhibitors. Part 1

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

N1 - Funding Information: We gratefully thank the National Science Council of Republic of China Grants NSC-94-2320-B-077-005 (L.-M.Y.) and NSC-94-2320-B-038-030 (S.-J.L.), and National Research Institute of Chinese Medicine for research funding (Grant NRICM-95-DMC-007). Copyright: Copyright 2008 Elsevier B.V., All rights reserved.

PY - 2006/9/1

Y1 - 2006/9/1

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.

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SN - 0960-894X

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

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ER -

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

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