Synthesis and structure analysis of cyclodehydration product of piroxicam: a metabolite detected in dogs and monkeys

Eur J Med Chem. 2009 Aug;44(8):3368-71. doi: 10.1016/j.ejmech.2009.03.010. Epub 2009 Mar 24.

Abstract

We report here a novel synthesis of 6-methyl-6H-7-oxopyrido[1,2-a]pyrimido[5,4-c]-1,2-benzothiazine-5,5-dioxide or cyclodehydration product of piroxicam, a metabolite detected in dogs and monkeys that was synthesized in 6% yield earlier. The reaction of benzoyl chloride with piroxicam in the presence of triethylamine afforded the piroxicam metabolite in good yield. A comparison of spectral data of the synthesized compound with the reported values remained inconclusive. The structure of the compound was confirmed unambiguously by single-crystal X-ray analysis.

MeSH terms

  • Acetates / chemistry
  • Animals
  • Crystallography, X-Ray
  • Dogs / metabolism*
  • Haplorhini / metabolism*
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Conformation
  • Piroxicam / chemical synthesis
  • Piroxicam / chemistry*
  • Piroxicam / metabolism*
  • Spectrum Analysis
  • Water / chemistry*

Substances

  • Acetates
  • Water
  • Piroxicam
  • ethyl acetate