Some reactions of 1,4-dihydropyridines with organic azides. Synthesis of 2,7-diazabicyclo[4.1.0]hept-3-enes with analgesic and antiprotozoal activity.
The 1,3-dipolar cycloaddition reaction of 1,4-dihydropyridines, 2, with organic azides, 3, afford 2,7-diazabicyclo[4.1.0]hept-3-enes, 4, which exhibit significant analgesic and antiprotozoal activities. The most active analgesics, 4a and 4c, were more potent than aspirin or dextropropoxyphene. Diazabicyclo[4.1.0]hept-3-enes 4a-e exert potent antiprotozoal activity, inhibiting growth of Trichomonas vaginalis at concentrations of less than 10 micrograms/mL of medium. The broad spectrum pharmacological screen also revealed moderate hypoglycemic (4a), antiinflammatory (4c), antidepressant (4d and 4e) and antihistaminic (4f) activities.
D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis*; D001386:Azides; D008297:Male; D051379:Mice; D011725:Pyridines; D013329:Structure-Activity Relationship
D000700:Analgesics; D000981:Antiprotozoal Agents; D001386:Azides; D011725:Pyridines