PMID: 2109057Feb 1, 1990Paper

Synthesis and structure-activity relationships of anti-inflammatory 9,10-dihydro-9-oxo-2-acridine-alkanoic acids and 4-(2-carboxyphenyl)aminobenzenealkanoic acids

Journal of Pharmaceutical Sciences
I B Taraporewala, J M Kauffman

Abstract

Eighteen test compounds, in three chemical series, were prepared as potential anti-inflammatory agents and evaluated by the rat hindpaw carrageenan-induced edema assay. The compounds, isosteric with known anti-inflammatory and antiallergic cyclo-oxygenase and lipoxygenase inhibitors, are 10-methyl-9,10-dihydro-9-oxo-2-acridinealkanoic acids, 9,10-dihydro-9-oxo-2-acridinealkanoic acids, and 4-(2-carboxyphenyl)aminobenzenealkanoic acids. Compounds within each of these series differ in the structure of the alkanoic acid side chain. Compounds containing the acetic acid and the branched 2-propionic acid side chain showed inhibition of carrageenan-induced edema. The activity of compounds with these side chains and the inactivity of those with carboxy, oxyacetic, thioacetic, and 3-propionic acid side chains is in accordance with the proposed template model of Appleton and Brown for the active site of cyclo-oxygenase, rather than with the alternative active site model proposed by Gund and Shen. One compound, (+-)-2-[N-(2-carboxyphenyl)-4-aminophenyl]propionic acid (3c), showed edema inhibition at 50 mg/kg po, comparable to that of an equivalent dose level of (+)-naproxen. Compounds 4a and 5a, which contain a carboxylic acid side chain,...Continue Reading

Citations

Jul 20, 2002·Chemical & Pharmaceutical Bulletin·Eleni RekkaAngeliki Kourounakis
Sep 25, 2014·Acta Crystallographica. Section E, Structure Reports Online·Antar A AbdelhamidJim Simpson
Jul 9, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Eleni PontikiGeorge Geromichalos
Mar 24, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Thalia LiargkovaConstantinos Avgoustakis
Jan 5, 2018·SAR and QSAR in Environmental Research·O KouatlyA Geronikaki
Jan 20, 2011·Chemical Biology & Drug Design·Asunción BurgueteAntonio Monge
Sep 24, 2009·Journal of Enzyme Inhibition and Medicinal Chemistry·Dimitra Hadjipavlou-LitinaDionissios Papaioannou
Sep 24, 2009·Journal of Enzyme Inhibition and Medicinal Chemistry·Zrinka RajićIvan Kosalec
Feb 16, 2015·Plant Foods for Human Nutrition·Felipe Jiménez-AspeeGuillermo Schmeda-Hirschmann
May 18, 2012·Journal of Enzyme Inhibition and Medicinal Chemistry·Michael G KallitsakisKonstantinos E Litinas
Nov 17, 2009·Journal of Enzyme Inhibition and Medicinal Chemistry·D Hadjipavlou-LitinaD Papaioannou
Jul 5, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Evangelia TsolakiAnil K Saxena
Aug 7, 2007·Journal of Enzyme Inhibition and Medicinal Chemistry·Dimitra Hadjipavlou-LitinaHaralambos E Katerinopoulos
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Maria Luiza ZeraikVanderlan S Bolzani
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ioanna KostopoulouAnastasia Detsi
Nov 24, 2004·European Journal of Pharmacology·Anna Tavridou, Vangelis G Manolopoulos
Sep 28, 2005·Bioorganic & Medicinal Chemistry·George N ZiakasPanos N Kourounakis
Nov 28, 2006·Bioorganic & Medicinal Chemistry·Ioanna C SiskouPanos N Kourounakis
Sep 15, 2005·Chemical Reviews·A S Michaelidou, D Hadjipavlou-Litina
Mar 4, 2008·Journal of Medicinal Chemistry·Athina A GeronikakiAnil K Saxena
Nov 27, 2009·European Journal of Medicinal Chemistry·Dimitra Hadjipavlou-LitinaDionissios Papaioannou
Oct 5, 2010·Bioorganic & Medicinal Chemistry·Angeliki P KourounakisAnastasios Nikitakis
Oct 5, 2010·European Journal of Medicinal Chemistry·Maria IspikoudiKonstantina C Fylaktakidou
Apr 22, 2011·Bioorganic & Medicinal Chemistry·Panagiota Moutevelis-MinakakisDimitra Hadjipavlou-Litina
Apr 26, 2011·European Journal of Medicinal Chemistry·A-M KatsoriD Hadjipavlou-Litina

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