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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

1,2, 3,4, 3,4, 3,4, 5, 5, 6, 1,2 and 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 / Revised: 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 14ah, 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 piroxicam; inflammation; pain; acylhydrazone; NSAID; COX
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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