In an effort to develop safe and potent anti-diabetic and anticancer agents, a series of novel pyrazine fused Indole derivatives II-(4a-4l) was prepared. It was synthesized via Schiff’s base with appropriately 2- aminopyrazine followed by n-benzoylation and Schiff’s base with substituted benzaldehydes. All the synthesized compounds were performed characterized by IR, 1HNMR and MASS spectral analysis and evaluated for their antidiabetic and anticancer activities. Various molecular properties have been predicted by using Qikprop module (Table.No.2) and most of the compounds were beyond the recommended range. Based on the predicted ADME parameters, majority of the compounds had predicted CNS activity. Compounds II4d, and II-4j had mostly inactive CNS activity. All the compounds except compounds II-4d (94.2%) and II4j (97.67%) had 100% human oral absorption and most of the 10 compounds (II-4a to II-4l) were not permeable through skin. The molecular docking studies were performed in order to find the possible protein ligand interactions of the dataset ligands. Glide dock scores of the dataset ligands were shown in Table 4 along with the interaction of amino acids including their number. Among the docked ligands, dock scores of all the compounds ranged from -9.2 (compound II-4c, II-4a) to -5.2 (compound II-4k). Finally, the anticancer activity was found by brine shrimp lethality bioassay and allium cepa root tip meristem model. Anti-diabetic activity was carried out by glucose diffusion inhibitory study. From the results, the compound II-4c (IC-50 value 47.82μg for antidiabetic) (38.01 μg/ml for anticancer) exhibited good activities.