Novel Chemical Transformations of Tenoxicam

✍ Scribed by Kristóf Kóczián; József Kökösi; Károly Mazák; Béla Noszál

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: German
• Weight: 107 KB
• Volume: 88
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200590171

✦ Synopsis

Both N-and O-substituted derivatives of the anti-inflammatory drug tenoxicam ( 4-hydroxy-2-methyl-N-(pyridin-2-yl)-2H-thieno[2,3-e] [1,2]thiazine-3-carboxamide 1,1-dioxide; 1) were synthesized, and various chemical transformations were investigated. Both selective hydrolysis and reaction of 1'-N-methyltenoxicam (5) with a variety of N-nucleophiles were performed (Scheme 1). Also, five new 4-O-acyl derivatives 10 were prepared as potential prodrugs (Scheme 2). The 4-chloro derivatives of 1 and its analog 8 could be successfully transformed into the novel tetra-and tricyclic ring systems 12 and 13, respectively, the latter being a conformationally restricted 1,5-diaryl-pyrazole designed as a potential COX-2 inhibitor.