Journal of Medicinal Chemistry p. 462 - 464 (1981)
Update date:2022-08-03
Topics: Synthesis Analgesic Experimental 1,4-dihydropyridines organic azides Antiprotozoal
Warren, Brent K.
Knaus, Edward E.
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.
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