New metal complexes of Schiff base (L) prepared from condensation reaction of 2-aminopyridine and 6-formyl-7-hydroxy-5-methoxy-2-methylbenzopyran-4-one with metal ions; Mn(II), Co(II), Ni(II) and Cu(II) are synthesized. Different analysis tools such as elemental analyses, FTIR, thermal analyses, conductivity, mass spectrometry, electronic spectra and magnetic susceptibility measurements are all used to elucidate the structures of the newly prepared metal complexes. The IR spectral data suggested that the ligand behaves as a monobasic bidentate ligand toward the central metal ion with ON donor atoms. The thermal decomposition kinetics of all complexes was estimated by Coats-Redfern. Ni-L and Co-L complexes were selected to study their thermal decomposition under non-isothermal conditions using Flynn-Wall-Ozawa and Starink methods at different three heating rates (5, 10 and 15°C min -1 ). The values of the activation energy (E) obtained by the all methods are in good agreement. All complexes are thermally stable as reflected from the high value of their activation energies. Ni-L complex has the highest thermal stability, and Mn-L complex has the lowest one indicating that Mn-L complex has fast rate of successive decomposition. The Schiff base L, Cu-L and Mn-L compounds were screened for in vitro cytotoxicity against normal standard fibroblast cells (3T3) using MTT assay. Among these compounds, Mn-L complex enhanced growth inhibition and cell death in a concentrationdependent manner for the standard fibroblast cells (3T3). Mn-L complex was then subjected against four human cancer cell lines; human hepatocellular carcinoma (Huh-7), human Hepatoblastoma (Hep G2) and human cervical cancer cells (HeLa & HeLa-Fas) for anticancer activity. Results indicate that Mn-L complex may be useful leads for anticancer drug development in the future.