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Molecules 2009, 14(2), 667-681; doi:10.3390/molecules14020667

Anti-inflammatory Activity and PGE2 Inhibitory Properties of Novel Phenylcarbamoylmethyl Ester-Containing Compounds

Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University, Kasr El-Eini Street, Cairo 11562, Egypt
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Received: 17 December 2008 / Revised: 2 February 2009 / Accepted: 6 February 2009 / Published: 11 February 2009
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Abstract

A variety of 4-(un)substituted phenylcarbamoyl methyl ester-containing compounds 3a-d, 5a-d and 7a-d were synthesized via reaction in N,N-dimethylformamide of (un)substituted chloroacetanilides 2a-d with the potassium salts of ibuprofen (1), naproxen (4) and N-acetylanthranilic acid (6). Moreover, other 4-(un)substituted phenylcarbamoylmethyl ester-containing compounds 10a-d were synthesized via the attack of (un)substituted chloroacetanilides 2a-d on one of the carboxylic acid groups of the potassium salt of 4-(2-carboxyethylcarboxamido)benzoic acid (8)in N,N-dimethylformamide, with subsequent cyclization of the other one giving finally a pyrrolidinone structure. Anti-inflammatory properties of the synthesized compounds were evaluated in vivo utilizing a standard acute carrageenan-induced paw oedema method in rats and the most promising prepared anti-inflammatory active agents were evaluated for ulcerogenic liability in rats using ibuprofen and naproxen as reference standards in both screenings. PGE2 inhibitory properties of the highly promising anti-inflammatory agents synthesized and low gastric ulcerogenic liabilities were tested with a PGE2 assay kit technique. View Full-Text
Keywords: Ibuprofen; Naproxen; 4-(Un)substituted phenylcarbamoylmethyl esters; Anti-inflammatory; Ulcerogenic liability; PGE2 Ibuprofen; Naproxen; 4-(Un)substituted phenylcarbamoylmethyl esters; Anti-inflammatory; Ulcerogenic liability; PGE2
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Barsoum, F.; Georgey, H.; Abdel-Gawad, N. Anti-inflammatory Activity and PGE2 Inhibitory Properties of Novel Phenylcarbamoylmethyl Ester-Containing Compounds. Molecules 2009, 14, 667-681.

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