Synthesis and anti-inflammatory activities of some N-[pyridyl(phenyl)carbonylamino]-tert-butyl/phenyl-1,2,3,6- tetrahydropyridines

Chem Pharm Bull (Tokyo). 1991 Mar;39(3):786-91. doi: 10.1248/cpb.39.786.

Abstract

Nucleophilic attack of tert-butyl/phenylpyridines 3 on 1-chloro-2,4-dinitrobenzene 4 results in the formation of tert-butyl/phenyl substituted 2,4-dinitrophenylpyridinium chlorides 5. Benzoyl hydrazide and pyridyl acid hydrazides 6 were reacted with the pyridinium chlorides 5 furnishing the 2,4-dinitroanilino derivatives 7, which were subsequently hydrolyzed with water: p-dioxane to yield N-[pyridyl(phenyl)carbonylimino]-tert-butyl/phenylpyridinium ylides 8. The title compounds 9, N-[pyridyl(phenyl)carbonylamino]-tert-butyl/phenyl-1,2,3,6- tetrahydropyridines, were obtained by sodium borohydride reduction of the pyridinium ylides 8. The anti-inflammatory activities of compounds 9a-p were determined using the carrageenan-soaked sponge model of inflammation in Sprague Dawley rats. All compounds tested showed moderate to good anti-inflammatory effects compared to indomethacin. Compounds 9b, 9c and 9p were the most active analogs of the group in this model.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacology
  • Rats

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Pyridines