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

Molecules

Volumn 17, Issue 12, 2012, Pages 14651-14672

  De Castro Barbosa, Maria Letícia ^a   Ramos, Thiago José Figueira ^b   De Arantes, Ana Carolina Santos ^b   Martins, Marco Aurélio ^b   Silva, Patrícia Machado Rodriguese ^b   Barreiro, Eliezer J ^a   Lima, Lídia Moreira ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b INSTITUTO OSWALDO CRUZ   (Brazil)

Author keywords

Inflammation; LASSBio 468; LASSBio 596; Phthalimide; TNF a

Indexed keywords

ANTIINFLAMMATORY AGENT; ISOINDOLE DERIVATIVE; LASSBIO 468; LASSBIO-468; LIPOPOLYSACCHARIDE; PHTHALIMIDE DERIVATIVE; SULFONAMIDE; TUMOR NECROSIS FACTOR ALPHA;

ANIMAL; ARTICLE; CHEMICALLY INDUCED DISORDER; CHEMISTRY; DRUG ANTAGONISM; METABOLISM; MOUSE; PATHOLOGY; PNEUMONIA; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ISOINDOLES; LIPOPOLYSACCHARIDES; MICE; PHTHALIMIDES; PNEUMONIA; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84871546857     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules171214651     Document Type: Article

References (32)

1. Moldoveanu, B.; Otmishi, P.; Jani, P.; Walker, J.; Sarmiento, X.; Guardiola, J.; Saad, M.; Yu, J. Inflammatory mechanisms in the lung. J. Inflamm. Res. 2009, 2, 1-11.
2. Medzhitov, R. Inflammation 2010: New adventures of an old flame. Cell 2010, 140, 771-776.
3. Dai, J.; Liu, B.; Li, Z. Regulatory T cells and Toll-like receptors: What is the missing link? Int. Immunopharmacol. 2009, 9, 528-533.
4. Mukhopadhyay, S.; Hoidal, J.R.; Mukherjee, T.K. Role of TNFα in pulmonary pathophysiology. Respir. Res. 2006, 7, 125.
5. Wheeler, A.P.; Bernard, G.R. Acute lung injury and the acute respiratory distress syndrome: A clinical review. Lancet 2007, 369, 1553-1564.
6. Hashimoto, Y. Structural development of biological response modifiers based on thalidomide. Bioorg. Med. Chem. 2002, 10, 461-479.
7. Barbosa, M.L.C.; Fumian, M.M.; Miranda, A.L.P.; Barreiro, E.J.; Lima, L.M. Therapeutic approaches for tumor necrosis factor inhibition. Braz. J. Pharm. Sci. 2011, 47, 427-446.
8. Lima, L.M.; Castro, P.; Machado, A.L.; Fraga, C.A.; Lugnier, C.; de Moraes, V.L.; Barreiro, E.J. Synthesis and anti-inflammatory activity of phthalimide derivatives, designed as new thalidomide analogues. Bioorg. Med. Chem. 2002, 10, 3067-3073.
9. Alexandre-Moreira, M.S.; Takiya, C.M.; de Arruda, L.B.; Pascarelli, B.; Gomes, R.N.; Castro Faria Neto, H.C.; Lima, L.M.; Barreiro, E.J. LASSBio-468: A new achiral thalidomide analogue which modulates TNF-alpha and NO production and inhibits endotoxic shock and arthritis in an animal model. Int. Immunopharmacol. 2005, 5, 485-494.
10. Lima, L.M.; Manssour Fraga, C.A.; Gonçalvez Koatz, V.L.; Barreiro, E.J. Thalidomide and analogs as anti-inflammatory and immunomodulator drug candidates. Anti-Inflamm. Anti-Allergy Agents Med. Chem. 2006, 5, 79-95.
11. Niwayama, S.; Turk, B.E.; Liu, J.O. Potent inhibition of tumor necrosis factor-alpha production by tetrafluorothalidomide and tetrafluorophthalimides. J. Med. Chem. 1996, 39, 3044-3045.
12. Muller, G.W.; Chen, R.; Huang, S.Y.; Corral, L.G.; Wong, L.M.; Patterson, R.T.; Chen, Y.; Kaplan, G.; Stirling, D.I. Amino-substituted thalidomide analogs: Potent inhibitors of TNF-alpha production. Bioorg. Med. Chem. Lett. 1999, 9, 1625-1630.
13. Gütschow, M.; Hecker, T.; Thiele, A.; Hauschildt, S.; Eger, K. Aza analogues of Thalidomide: Synthesis and evaluation as inhibitors of tumor necrosis factor-α production in vitro. Bioorg. Med. Chem. 2001, 9, 1059-1065.
14. Bastos, R.S.; da Cunha, A.S.; da Silva, L.C.; de Oliveira, C.C.P.; Rezende, C.M.; Pinto, A.C. Preparo da para-cloroanilina: Um experimento simples, rápido e barato. Quim. Nova 2008, 31, 172-173.
15. Barbosa, M.L.C.; Melo, G.M.A.; Cupertino da Silva, Y.K.; Lopes, R.O.; de Souza, E.T.; de Queiroz, A.C.; Smaniotto, S.; Alexandre-Moreira, M.S.; Barreiro, E.J.; Lima, L.M. Synthesis and pharmacological evaluation of N-phenyl-acetamide sulfonamides designed as novel non-hepatotoxic analgesic candidates. Eur. J. Med. Chem. 2009, 44, 3612-3620.
16. Stewart, J. Sulfonation of acetanilide. J. Chem. Soc. 1922, 121, 2558.
17. Furniss, B.S.; Hannaford, A.J.; Rogers, V.; Smith, P.W.G.; Tatchell, A.R. Vogel's Textbook of Practical Organic Chemistry, 4th ed.; Longmann: London, UK, 1978.
18. Cremlyn, R.J.; Swinbourne, F.J.; Nunes, R.J. Phthalimidobenzenesulphonyl derivatives. Quim. Nova 1985, 8, 61-62.
19. Almansa, C.; Alfón, J.; de Arriba, A.F.; Cavalcanti, F.L.; Escamilla, I.; Gómez, L.A.; Miralles, A.; Soliva, R.; Bartrolí, J.; Carceller, E.; et al. Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. J. Med. Chem. 2003, 46, 3463-3475.
20. Capitosti, S.M.; Hansen, T.P.; Brown, M.L. Thalidomide analogues demonstrate dual inhibition of both angiogenesis and prostate cancer. Bioorg. Med. Chem. 2004, 12, 327-336.
21. Trujillo-Ferrara, J.; Correa-Basurto, J.; Espinosa, J.; García, J.; Martínez, F.; Miranda, R. Solvent-free synthesis of arylamides and arylimides, analogues of acetylcholine. Synth. Commun. 2005, 35, 2017-2023.
22. Julémont, F.; de Leval, X.; Michaux, C.; Damas, J.; Charlier, C.; Durant, F.; Pirotte, B.; Dogné, J.-M. Spectral and crystallographic study of pyridinic analogues of nimesulide: Determination of the active form of methanesulfonamides as COX-2 selective inhibitors. J. Med. Chem. 2002, 45, 5182-5185.
23. Brewster, J.H.; Fusco, A.M.; Carosino, L.E.; Corman, B.G. Reduction of phthalic acid and its derivatives by zinc. J. Org. Chem. 1963, 28, 498-501.
24. Eisch, J.J.; Sanchez, R. Selective, oxophilic imination of ketones with bis(dichloroaluminum) phenylimide. J. Org. Chem. 1986, 51, 1848-1852.
25. Hashimoto, Y. Novel biological response modifiers derived from thalidomide. Curr. Med. Chem. 1998, 5, 163-178.
26. Collin, X.; Robert, J.-M.; Wielgosz, G.; Le Baut, G.; Bobin-Dubigeon, C.; Grimaud, N.; Petit, J.-Y. New anti-inflammatory N-pyridinyl(alkyl)phthalimides acting as tumour necrosis factor-α production inhibitors. Eur. J. Med. Chem. 2001, 36, 639-649.
27. Schumacher, H.; Smith, R.L.; Williams, R.T. The metabolism of thalidomide: The spontaneous hydrolysis of thalidomide in solution. Br. J. Pharmacol. Chemother. 1965, 25, 324-337.
28. Melchert, M.; List, A. The thalidomide saga. Int. J. Biochem. Cell Biol. 2007, 39, 1489-1499.
29. Rocco, P.R.M.; Xisto, D.G.; Silva, J.D.; Diniz, M.F.F.M.; Almeida, R.N.; Luciano, M.N.; Medeiros, I.A.; Cavalcanti, B.C.; Ferreira, J.R.O.; de Moraes, M.O.; et al. LASSBio-596: Da descoberta aos ensaios pré-clínicos. Rev. Virtual Quim. 2010, 2, 10-27.
30. Lee, Y.M.; Moon, M.U.; Vajpayee, V.; Filimonov, V.D.; Chi, K.W. Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts. Tetrahedron 2010, 66, 7418-7422.
31. Cragoe, E.J., Jr.; Hamilton, C.S. The synthesis of arsenicals containing certain heterocyclic Nuclei. J. Am. Chem. Soc. 1945, 67, 536-539.
32. Pons, M.; Feliz, M.; Giralt, E. 13C-NMR spectra of fluorinated molecules using 19F-13C polarization transfer. Tetrahedron Lett. 1985, 26, 2817-2820.