A new set of 1H-indenopyrdine-based derivatives were synthesized using the compound 4-(4-hydroxy-3-methoxyphenyl)-2-oxo-2,5-dihydro-1H-indeno[1,2-b]pyridine-3-carbonitrile (1) as the key starting compound. The molecular structures of the new derivatives were identified using various spectroscopic techniques and elemental analysis. All the new analogues were screened as antimicrobial against different strains of +ve gm, -ve gm bacteria and the opportunistic pathogenic yeast C. albicans. Some of the new indenopyrdines exhibited moderate antimicrobial activity comparing to gentamicin as a standard drug. On the reverse, the free radical scavenging activity of the new compounds using DPPH assay protocol revealed that most of the compounds were potent antioxidant agents while comparing to ascorbic acid as a positive antioxidant control.