Design, Synthesis, Antinociceptive and Anti-Inflammatory Activities of Novel Piroxicam Analogues

doi:10.3390/molecules171214126

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Molecules 2012, 17(12), 14126-14145; doi:10.3390/molecules171214126

Article

Design, Synthesis, Antinociceptive and Anti-Inflammatory Activities of Novel Piroxicam Analogues

Amanda Silva de Miranda^1,2, Walfrido Bispo Júnior^3,4, Yolanda Karla Cupertino da Silva^3,4, Magna Suzana Alexandre-Moreira^3,4, Rosane de Paula Castro⁵, José Ricardo Sabino⁵, Luciano Morais Lião⁶, Lídia Moreira Lima^1,2 and Eliezer J. Barreiro^1,2,*

¹ Bio® – Laboratório de Avaliação e Síntese de Substâncias Bioativas, Faculdade de Farmácia, Universidade Federal do Rio de Janeiro, P.O. Box 68024, 21944-971, Rio de Janeiro, RJ, Brazil ² Química, Instituto de Química, Universidade Federal do Rio de Janeiro, 21941-909, Rio de Janeiro, RJ, Brazil ³ LaFI – Laboratório de Farmacologia e Imunidade, Instituto de Ciências Biológicas e da Saúde, Universidade Federal de Alagoas, 57072-970, Maceió, AL, Brazil ⁴ Rede Nordeste de Biotecnologia, Universidade Federal de Alagoas, 57072-970, Maceió, AL, Brazil ⁵ Instituto de Física, Universidade Federal de Goiás, 74001-970, Goiânia, GO, Brazil ⁶ Instituto de Química, Universidade Federal de Goiás, 74001-970, Goiânia, GO, Brazil

* Author to whom correspondence should be addressed.

Received: 6 November 2012; in revised form: 19 November 2012 / Accepted: 20 November 2012 / Published: 28 November 2012

(This article belongs to the Section Medicinal Chemistry)

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Abstract: In this paper we report the design, synthesis, antinociceptive and anti-inflammatory activities of a series of benzothiazine N-acylhydrazones 14a–h, planned by structural modification of piroxicam (1), a non steroidal anti-inflammatory drug. Among the synthesized analogues, compounds 14f (LASSBio-1637) and 14g (LASSBio-1639) were identified as novel antinociceptive and anti-inflammatory prototypes, active by oral administration, acting by a mechanism of action that seems to be different from that of piroxicam, since they were inactive as an inhibitor of cyclooxygenase (COX-1 and COX-2) at concentrations of 10 mM.

Keywords: piroxicam; inflammation; pain; acylhydrazone; NSAID; COX

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Cite This Article

MDPI and ACS Style

de Miranda, A.S.; Júnior, W.B.; da Silva, Y.K.C.; Alexandre-Moreira, M.S.; Castro, R.P.; Sabino, J.R.; Lião, L.M.; Lima, L.M.; Barreiro, E.J. Design, Synthesis, Antinociceptive and Anti-Inflammatory Activities of Novel Piroxicam Analogues. Molecules 2012, 17, 14126-14145.

AMA Style

de Miranda AS, Júnior WB, da Silva YKC, Alexandre-Moreira MS, Castro RP, Sabino JR, Lião LM, Lima LM, Barreiro EJ. Design, Synthesis, Antinociceptive and Anti-Inflammatory Activities of Novel Piroxicam Analogues. Molecules. 2012; 17(12):14126-14145.

Chicago/Turabian Style

de Miranda, Amanda S.; Júnior, Walfrido B.; da Silva, Yolanda K.C.; Alexandre-Moreira, Magna S.; Castro, Rosane P.; Sabino, José R.; Lião, Luciano M.; Lima, Lídia M.; Barreiro, Eliezer J. 2012. "Design, Synthesis, Antinociceptive and Anti-Inflammatory Activities of Novel Piroxicam Analogues." Molecules 17, no. 12: 14126-14145.

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