Novel series of chrysin compound containing the organosulfur moiety from the Schiff bases derived from chrysin and 2-(phenylthio)aniline and their copper complexes were synthesized. They were characterized using analytical and spectral techniques. All the Cu(II) complexes exhibit the distortion square planar geometry. The in vitro antimicrobial activities of the investigated compounds were tested against the bacterial species, Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, and Klebsiella pneumoniae and fungal species, Aspergillus niger, Fusarium solani, Rhizoctonia bataicola and Candida albicans by disc diffusion process. Free radical scavenging, superoxide dismutase, glutathione peroxidase and antioxidant activities of the copper complexes have also been studied. The DNA-cleavage activities of Cu(II) complexes, have been investigated by using agarose gel electrophoresis. Furthermore, interaction of copper complexes with bovine serum albumin was investigated by fluorescence spectrometry. The anticancer activities of the complexes have been carried out towards HeLa and HCT116 cancer cells. The pretreatment of chrysin compounds containing the organosulfur moiety of Cu(II) complexes ([CuHL4l(OAc)], [CuHL4m(OAc)] and [CuHL4n(OAc)]) elicited marked anti-inflammtory effects in carrageenan induced paw edema test in mice during various assessment times (1–5 hrs).