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Cyclooxygenase-2 inhibitors. 1,5-diarylpyrrol-3-acetic esters with enhanced inhibitory activity toward cyclooxygenase-2 and improved cyclooxygenase-2/ cyclooxygenase-1 selectivity

Journal of Medicinal Chemistry, ISSN: 0022-2623, Vol: 50, Issue: 22, Page: 5403-5411
2007
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Article Description

The important role of cyclooxygenase-2 (COX-2) in the pathogenesis of inflammation and side effect limitations of current COX-2 inhibitor drugs illustrates a need for the design of new compounds based on alternative structural templates. We previously reported a set of substituted 1,5-diarylpyrrole derivatives, along with their inhibitory activity toward COX enzymes. Several compounds proved to be highly selective COX-2 inhibitors and their affinity data were rationalized through docking simulations. In this paper, we describe the synthesis of new 1,5-diarylpyrrole derivatives that were assayed for their in vitro inhibitory effects toward COX isozymes. Among them, the ethyl-2-methyl-5-[4-(methylsulfonyl)phenyl]-1-[3-fluorophenyl]-1H-pyrrol-3- acetate (1d), which was the most potent and COX-2 selective compound, also showed a very interesting in vivo anti-inflammatory and analgesic activity, laying the foundations for developing new lead compounds that could be effective agents in the armamentarium for the management of inflammation and pain. © 2007 American Chemical Society.

Bibliographic Details

Biava, Mariangela; Porretta, Giulio Cesare; Poce, Giovanna; Supino, Sibilla; Forli, Stefano; Rovini, Michele; Cappelli, Andrea; Manetti, Fabrizio; Botta, Maurizio; Sautebin, Lidia; Rossi, Antonietta; Pergola, Carlo; Ghelardini, Carla; Vivoli, Elisa; Makovec, Francesco; Anzellotti, Paola; Patrignani, Paola; Anzini, Maurizio

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Pharmacology, Toxicology and Pharmaceutics

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