Three novel metal complexes of 4-Amino-6-oxo-5-thiophen-2-yl-8-thioxo-3,5,6,7,8,9-hexahydro- 4Hpyrano[2,3-d; 6,5d']dipyrimidin-2-yl)-acetonitrile(L1),5-Thiophen-2-yl-2-thioxo-2,3,5,7-tetrahydro- 1H-pyrano[2,3-d; 6,5-d']dipyrimidine-4,6-dione (L2) and 6-Amino-5-thiophen-2-yl-2-thioxo-1,2,3,5- tetrahydro-pyrano[2,3-d; 6,5-d']dipyrimidin-4-one (L3) with Mn(II) were synthesized and characterized with physicochemical and spectroscopic techniques. The electron density of HOMOs is localized on the dipyrimidin-4-on ring, specially on the donating centers, N1 of amino group, O7 of C]O group and S8 of C]S group. The Infrared spectra suggest that three ligands (L1, L2 and L3) interact with metal ions as a tridentate. As a potential application, the ligands in comparison with the newly synthesized metal complexes were screened for its anticancer activity against breast cancer cell line (MCF-7) and colon cancer cell line (HCT-116). The [Mn(L3)Cl2(H2O)].H2O complex has higher anti-breast cancer activity than free ligand. The antibacterial and antifungal activities of the ligands, metal salt and its complexes were tested against some microorganisms (bacteria and fungi). The complexes showed increment antibacterial and antifungal profile in comparison with the free ligands