Some Reactions of 1,4-Dihydropyridines with Organic Azides. Synthesis of 2,7-Diazabicyclohept-3-enes with Analgesic and Antiprotozoal Activity

Article abstract of DOI:10.1021/jm00136a017

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 μg/mL of medium.The broad spectrum pharmacological screen also revealed moderate hypoglycemic (4a), antiinflammatory (4c), antidepressant (4d and 4e) and antihistaminic (4f) activities.