Copper catalyzed azide-alkyne cycloaddition was used for the first time to access a small series of eight novel 1,2,3-triazole linked isoflavone benzodiazepine hybrids. As part of this work, a previously unreported alkyne substituted pyrrolo[1,4]benzodiazepine was synthesized using a Sonogashira coupling reaction. Two previously unreported azide substituted isoflavones were also synthesized using TMS-azide as a key reagent. The eight new 1,2,3-triazole linked products, and several precursors, were evaluated as potential anti-inflammatory compounds. This revealed that two of the triazole linked isoflavone benzodiazepine hybrids together with one of the azido-isoflavone precursors showed useful NO inhibitory activity when compared to natural isoflavones.