In this study, firstly, (4R)-2-(3-hydroxyphenyl)thiazolidine-4-carboxylic acid (1) and (4R)-2-(3-(3,4-dicyanophenoxy)phenyl)thiazolidine-4-carboxylic acid (2) were prepared. Then, the novel type metallophthalocyanines (ZnPc (3), CuPc (4), and CoPc (5)) bearing thiazolidine groups in peripheral positions were synthesized using by compound (2). The synthesized new compounds (1-5) were characterized by the combination of standard spectroscopic methods such as FT-IR, H-1 NMR, C-13 NMR, UV-Vis spectral data, and MALDI-TOF. Aggregation behaviors of peripheral tetra-substituted metallophthalocyanines were investigated in dimethyl sulfoxide (DMSO) media. Fluorescence properties and fluorescence quantum yield of the new type zinc phthalocyanine (3) were performed in DMSO at room temperature. The anticancer activity of novel type metallophthalocyanines bearing thiazolidine groups in peripheral positions were investigated on rat glioma cancer (C6), human prostate carcinoma (DU-145), and normal human lung fibroblast (WI-38) cell lines. Finally, the biological and chemical activities of (4R)-2-(3-(3,4-dicyanophenoxy)phenyl)thiazolidine-4-carboxylic acid (2) and its novel type metallophthalocyanines (ZnPc (3), CuPc (4), and CoPc (5)) have been compared with many parameters obtained using theoretical methods that are the Gaussian software and molecular docking.