Synthesis of N-(carbonylamino)-1,2,3,6-tetrahydropyridines with analgesic, antiinflammatory, and hyperglycemic activity

J Med Chem. 1982 Feb;25(2):191-5. doi: 10.1021/jm00344a020.

Abstract

A group of N-(carbonylamino)-1,2,3,6-tetrahydropyridines was synthesized to investigate the effects that changes in functionality at the carbonyl group have on analgesic, antiinflammatory, and hyperglycemic activities. One of the most active analgesic compounds was N-[(ethoxycarbonyl)amino]-1,2,3,6-tetrahydropyridine (5o), which was comparable to that of morphine. Pretreatment with naloxone did not alter the activity of 5o or 5q. N-[(2-Furanylcarbonyl)amino]-1,2,3,6-tetrahydropyridine (5q) was the most potent hyperglycemic agent, elevating blood glucose 181% at 2 and 4 h after a 100 mg/kg po dose.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Analgesics / chemical synthesis*
  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Blood Glucose / metabolism*
  • Chemical Phenomena
  • Chemistry
  • Female
  • Male
  • Mice
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacology
  • Rats
  • Rats, Inbred Strains

Substances

  • Analgesics
  • Anti-Inflammatory Agents
  • Blood Glucose
  • Pyridines