Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response

In this paper we report the design, synthesis and pharmacological evaluation of a new series of phenyl sulfonamide derivatives 2a-h and 3-8 planned by structural modification on the anti-inflammatory prototype LASSBio-468 (1). Among the synthesized analogues, the tetrafluorophthalimide LASSBio-1439...

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Published in:	Molecules (Basel, Switzerland) Vol. 17; no. 12; pp. 14651 - 14672
Main Authors:	Barbosa, Maria Letícia de Castro, Ramos, Thiago José Figueira, de Arantes, Ana Carolina Santos, Martins, Marco Aurélio, Silva, Patrícia Machado Rodrigues E, Barreiro, Eliezer J, Lima, Lídia Moreira
Format:	Journal Article
Language:	English
Published:	Switzerland MDPI AG 10-12-2012 MDPI
Subjects:	Animals Anti-Inflammatory Agents - administration & dosage Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - chemistry Asthma Chronic obstructive pulmonary disease Design Inflammation Isoindoles - chemistry Isoindoles - therapeutic use LASSBio-468 LASSBio-596 Lipopolysaccharides - toxicity Mice phthalimide Phthalimides - administration & dosage Phthalimides - chemical synthesis Pneumonia - chemically induced Pneumonia - drug therapy Pneumonia - pathology Reagents Signal transduction Structure-Activity Relationship Sulfonamides - administration & dosage Sulfonamides - chemical synthesis Sulfonamides - chemistry TNF-&#945 Tumor Necrosis Factor-alpha - antagonists & inhibitors Tumor Necrosis Factor-alpha - metabolism Tumor necrosis factor-TNF Brazil Rio de Janeiro Brazil
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Abstract	In this paper we report the design, synthesis and pharmacological evaluation of a new series of phenyl sulfonamide derivatives 2a-h and 3-8 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.
AbstractList	In this paper we report the design, synthesis and pharmacological evaluation of a new series of phenyl sulfonamide derivatives 2a–h and 3–8 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. In this paper we report the design, synthesis and pharmacological evaluation of a new series of phenyl sulfonamide derivatives 2a-h and 3-8 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. In this paper we report the design, synthesis and pharmacological evaluation of a new series of phenyl sulfonamide derivatives 2a – h and 3 – 8 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 .
Author	Martins, Marco Aurélio Barreiro, Eliezer J Ramos, Thiago José Figueira Barbosa, Maria Letícia de Castro Silva, Patrícia Machado Rodrigues E Lima, Lídia Moreira de Arantes, Ana Carolina Santos
AuthorAffiliation	2 Graduate Program of Chemistry (PGQu), Chemistry Institute, Federal University of Rio de Janeiro, Rio de Janeiro, 21941-909, RJ, Brazil 1 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 3 Laboratory of Inflammation—Oswaldo Cruz Institute, Oswaldo Cruz Foundation (FIOCRUZ), Rio de Janeiro, 21045-900, RJ, Brazil
AuthorAffiliation_xml	– name: 3 Laboratory of Inflammation—Oswaldo Cruz Institute, Oswaldo Cruz Foundation (FIOCRUZ), Rio de Janeiro, 21045-900, RJ, Brazil – name: 1 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 – name: 2 Graduate Program of Chemistry (PGQu), Chemistry Institute, Federal University of Rio de Janeiro, Rio de Janeiro, 21941-909, RJ, Brazil
Author_xml	– sequence: 1 givenname: Maria Letícia de Castro surname: Barbosa fullname: Barbosa, Maria Letícia de Castro organization: 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 – sequence: 2 givenname: Thiago José Figueira surname: Ramos fullname: Ramos, Thiago José Figueira – sequence: 3 givenname: Ana Carolina Santos surname: de Arantes fullname: de Arantes, Ana Carolina Santos – sequence: 4 givenname: Marco Aurélio surname: Martins fullname: Martins, Marco Aurélio – sequence: 5 givenname: Patrícia Machado Rodrigues E surname: Silva fullname: Silva, Patrícia Machado Rodrigues E – sequence: 6 givenname: Eliezer J surname: Barreiro fullname: Barreiro, Eliezer J – sequence: 7 givenname: Lídia Moreira surname: Lima fullname: Lima, Lídia Moreira
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/23222927$$D View this record in MEDLINE/PubMed
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SubjectTerms	Animals Anti-Inflammatory Agents - administration & dosage Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - chemistry Asthma Chronic obstructive pulmonary disease Design Inflammation Isoindoles - chemistry Isoindoles - therapeutic use LASSBio-468 LASSBio-596 Lipopolysaccharides - toxicity Mice phthalimide Phthalimides - administration & dosage Phthalimides - chemical synthesis Pneumonia - chemically induced Pneumonia - drug therapy Pneumonia - pathology Reagents Signal transduction Structure-Activity Relationship Sulfonamides - administration & dosage Sulfonamides - chemical synthesis Sulfonamides - chemistry TNF-&#945 Tumor Necrosis Factor-alpha - antagonists & inhibitors Tumor Necrosis Factor-alpha - metabolism Tumor necrosis factor-TNF
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Title	Synthesis and pharmacological evaluation of novel phenyl sulfonamide derivatives designed as modulators of pulmonary inflammatory response
URI	https://www.ncbi.nlm.nih.gov/pubmed/23222927 https://www.proquest.com/docview/1531938611 https://pubmed.ncbi.nlm.nih.gov/PMC6268662 https://doaj.org/article/8b16ce12ee7a4efe8c6700c3b4a3a081
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