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.
D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis*; D001786:Blood Glucose / Q000378:metabolism*; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D008297:Male; D051379:Mice; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D011919:Rats, Inbred Strains
D000700:Analgesics; D000893:Anti-Inflammatory Agents; D001786:Blood Glucose; D011725:Pyridines