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

• Main Authors: Eliezer J. Barreiro, Lídia Moreira Lima, Rosane de Paula Castro, José Ricardo Sabino, Luciano Morais Lião, Magna Suzana Alexandre-Moreira, Walfrido Bispo Júnior, Yolanda Karla Cupertino da Silva, Amanda Silva de Miranda
• Format: Article
• Language: English
• Published: MDPI AG 2012-11-01
• Series: Molecules
• Subjects: piroxicam; inflammation; pain; acylhydrazone; NSAID; COX
• Online Access: http://www.mdpi.com/1420-3049/17/12/14126
• ISSN: 1420-3049

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.