The new diamine 2,20-(piperazine-1,4-diylbis(methylene))dianiline (A1) was synthesized by reaction of 2-nitrobenzylchloride and piperazine. Its corresponding Mn(II) and Zn(II) macrocyclic Schiff-base complexes were prepared via the metal templated [1+1] cyclocondensation of this diamine and 2,6-diacetylpyridine or 2,6-pyridinedicarbaldehyde. The diamine and all the macrocyclic complexes were characterized by elemental analysis, mass spectrometry and spectroscopic methods such as: FT-IR, 1H and 13C NMR. Also, the crystal structures of [MnL1(ClO4)2] (1) and [ZnL1(H2O)2](ClO4)2 (3) complexes were obtained by single-crystal X-ray crystallography. The cytotoxic properties of all macrocyclic complexes were studied. The results showed, some of these complexes were more potent than doxorubicin in U87 MG cell line predicating their therapeutic potential in treatment of glioblastoma. Also, the complexes were tested for in vitro antibacterial properties against some Gram-positive and Gram-negative bacteria. The complexes had antibacterial properties and in some cases even more than those of Tobramycin and Tetracycline as standards.