Antiinflammatory agents. 4. Syntheses and biological evaluation of potential prodrugs of 2-amino-3-benzoylbenzeneacetic acid and 2-amino-3-(4-chlorobenzoyl)benzeneacetic acid

  • J Med Chem. 1990 Aug;33(8):2296-304. doi: 10.1021/jm00170a039.
D A Walsh  1 ,  H W Moran ,  D A Shamblee ,  W J Welstead Jr ,  J C Nolan ,  L F Sancilio ,  G Graff
Affiliations
  • 1. Department of Chemical Research, A.H. Robins Company, Richmond, Virginia 23261-6609.
PMID: 2115589 DOI: 10.1021/jm00170a039
Abstract

A series of potential prodrugs of 2-amino-3-benzoylbenzeneacetic acid (amfenac) and 2-amino-3-(4-chlorobenzoyl)benzeneacetic acid were synthesized and evaluated for their cyclooxygenase inhibiting properties, antiinflammatory potency, and gastrointestinal irritation liability. One compound, 2-amino-3-(4-chlorobenzoyl)benzeneacetamide, possessed a therapeutic index 1 order of magnitude greater than that of indomethacin.

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