The chemical behavior of 4-(dimethylaminomethylene)-1-phenyl-3-(pyridin-3-yl)-1H-pyrazol-5(4H)-one (enaminone) (2) toward some active methylene reagents has been reported to give pyrazolopyridine derivatives. All the reactions were carried out by conventional heating and microwave irradiation technique. The antioxidant activity of the prepared compounds was studied using 1,1-phenyl-2-picrylhydrazyl (DPPH) assay. Compounds (4c) and (4d) showed the highest activity. The antitumor activity against liver and breast cell lines was tested. Compounds (6), (9) and (11) showed the highest activity for liver cell line while compounds (6) and (9) showed the highest activity for breast cell line. Compounds (4a–d) were screened for their antibacterial activity against Gram-positive, Gram-negative bacteria and antifungal activity.