The synthesis of a novel series of Schiff bases of 2-hydroxy-6-chloro-3-formylquinoline (4a–e) and its Zn (II) and Cu (II) complexes are described in the present paper. The chemical structures of compounds have been elucidated by IR, 1H NMR and Mass spectral data. Fluorescence properties of all the synthesized compounds have been tested. Molecular modeling tools were also used for a further analysis in order to estimate the druggability of the reported quinoline Schiff base derivatives.