The present study describes mono substituted indeno [1,2-b] quinolines (3 a-c and 5) have much more antiproliferative potentials than positive controls against A549, HeLa, MCF7 and Hep3B cell lines (IC 50 values 1.1-29.6 μg/mL) and show similar cytotoxicity (14.3 % to 19.8 %) to cells such as controls. Moreover, the mono substituted indeno[1,2-b]quinoline amines (3 ac and 5) exhibit significant antimicrobial activity with MIC values between 15.62 μg/mL and 250 μg/mL. The compounds can also bind to DNA in the groove binding mode with a binding constant range of 1.1 × 10 3 -1.1 × 10 5 M À 1 . The anticancer and antibacterial properties of compounds were confirmed with the molecular docking simulation for their pharmacokinetic. As a result, the preliminary experimental data and a multi-criteria decision-making methodology (MCDM) indicated that the mono substituted indeno[1,2-b]quinoline amine derivatives, especially 3 a and 5, exhibit effective pharmacological properties. parameters and their interaction with related cells at the molecular level.