In the present study, we describe the synthesis of a new set of 1,2,4-triazolo[1,5-a]pyridines and their fused ring systems. The products were assayed for various types of biological activities like anti-inflammatory and antioxidative activity. Compounds 4c, 4f, 12a, 14, 16, and 19 were found to reduce carrageenan- and dextran-induced inflammation in rats. In addition, compounds 4f and 12a were found to have antioxidative radical scavenging activity. Furthermore, these compounds were tested in the model system Caenorhabiditis elegans and there increased heat stress resistance, reduced the formation of advanced glycation end products, and finally extended the life span.