A new series of coumarin linked imidazo[2,1-b][1,3,4]thiadiazoles were synthesized and evaluated for their cytotoxicity against human T-lymphocyte (CEM), human cervix carcinoma (HeLa) and murine leukemia cells (L1210). Among the tested compounds, 3-[5-bromo-2-(thiophen-2-ylmethyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]-2H-chromen-2-one 9b exhibited cytotoxicity at 0.77 μM against CEM, 1.6 μM against L1210and 0.38 μM against HeLa cells and, 6-(2-oxo-2H-chromen-3-yl)-2-(thiophen-2-ylmethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-carbaldehyde 10b showed cytotoxicity at 3.5 μM against CEM and at 9.5 μM against HeLa cells. Further, molecular docking simulations performed to evaluate the possibility of synthesized analogs as inhibitors of heat shock protein 90 (Hsp90), Pdb ID: 1UYL revealing that docking predictions are in good agreement with in-vitro results (-10.7 for 9b and -10.5 for 10b). The in-silico ADME parameters, pharmacokinetics and drug-likeness of all derivatives were examined in detail using Swiss ADME webserver. Better stability exhibited by 8b, 9a, 10b and 11b during molecular dynamics simulation experiments.