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Molecules 2012, 17(12), 14651-14672; doi:10.3390/molecules171214651

Synthesis and Pharmacological Evaluation of Novel Phenyl Sulfonamide Derivatives Designed as Modulators of Pulmonary Inflammatory Response

Laboratory of Evaluation and Synthesis of Bioactive Substances (LASSBio®), Federal University of Rio de Janeiro, P.O. Box 68024, 21944-971, Rio de Janeiro, RJ, Brazil
Graduate Program of Chemistry (PGQu), Chemistry Institute, Federal University of Rio de Janeiro, Rio de Janeiro, 21941-909, RJ, Brazil
Laboratory of Inflammation—Oswaldo Cruz Institute, Oswaldo Cruz Foundation (FIOCRUZ), Rio de Janeiro, 21045-900, RJ, Brazil
Author to whom correspondence should be addressed.
Received: 17 October 2012 / Revised: 19 November 2012 / Accepted: 5 December 2012 / Published: 10 December 2012
(This article belongs to the Section Medicinal Chemistry)
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In this paper we report the design, synthesis and pharmacological evaluation of a new series of phenyl sulfonamide derivatives 2ah and 38 planned by structural modification on the anti-inflammatory prototype LASSBio-468 (1). Among the synthesized analogues, the tetrafluorophthalimide LASSBio-1439 (2e) stands out showing an in vitro anti-TNF-α effect similar to the standard thalidomide. The relevance of tetrafluorination of the phthalimide nucleus was also confirmed by the anti-inflammatory profile of 2e, through oral administration, in a murine model of pulmonary inflammation. The corresponding tetrafluorocarboxyamide metabolite LASSBio-1454 (15), generated from partial hydrolysis of the derivative 2e, presented a significant in vitro effect and a pronounced anti-inflammatory activity in vivo.
Keywords: inflammation; TNF-α; LASSBio-468; LASSBio-596; phthalimide inflammation; TNF-α; LASSBio-468; LASSBio-596; phthalimide

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Barbosa, M.L.C.; Ramos, T.J.F.; de Arantes, A.C.S.; Martins, M.A.; Silva, P.M.R.; Barreiro, E.J.; Lima, L.M. Synthesis and Pharmacological Evaluation of Novel Phenyl Sulfonamide Derivatives Designed as Modulators of Pulmonary Inflammatory Response. Molecules 2012, 17, 14651-14672.

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