In this work, in vitro antibacterial and Leishmanicidal activities of a ligand and phthalocyanine derivatives (2, 3, 3a–3c and 4) were tested for six selected standard bacteria and one Leishmania species. The synthesis of fluorinated pyrazoline compound (2) was first carried out from a chalcone precursor (1). Then, peripherally tetra-substituted metallophthalocyanines (zinc(II) (3a), cobalt(II) (3b) and iron(II) (3c)) and axially di-substituted silicon(IV) (4) containing fluorinated pyrazoline groups were obtained. The characterizations of 2, 3, 3a–3c and 4 were performed by IR,1H and 13C NMR, MALDI-TOF-MS and UV-Vis spectra and elemental analyses. The antibacterial and Leishmanicidal activities of the pyrazoline and phthalocyanine compounds were investigated.