Synthesis and evaluation of 1,5-diaryl-substituted tetrazoles as novel selective cyclooxygenase-2 (COX-2) inhibitors.

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Al-Hourani BJ, Sharma SK, Mane JY, Tuszynski J, Baracos V, Kniess T, Suresh M, Pietzsch J, Wuest F

Synthesis and evaluation of 1,5-diaryl-substituted tetrazoles as novel selective cyclooxygenase-2 (COX-2) inhibitors.

Bioorg Med Chem Lett. 2011 Mar 15;21(6):1823-6. doi: 10.1016/j.bmcl.2011.01.057. Epub 2011 Jan 21.

PubMed ID

21316237 [ View in PubMed

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Abstract

A series of 1,5-diaryl-substituted tetrazole derivatives was synthesized via conversion of readily available diaryl amides into corresponding imidoylchlorides followed by reaction with sodium azide. All compounds were evaluated by cyclooxygenase (COX) assays in vitro to determine COX-1 and COX-2 inhibitory potency and selectivity. Tetrazoles 3a-e showed IC(50) values ranging from 0.42 to 8.1 mM for COX-1 and 2.0 to 200 muM for COX-2. Most potent compound 3c (IC(50) (COX-2)=2.0 muM) was further used in molecular modeling docking studies.

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Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Celecoxib	Prostaglandin G/H synthase 2	IC 50 (nM)	30	N/A	N/A	Details