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

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.