Following a 1:1 molar ratio condensation of ethyl 2-amino 5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate with various aryl aldehydes, tridentate Schiff bases were produced. These novel aminothiophene Schiff bases were synthesised as zinc chloride complexes using a metal:ligand ratio of 1:1. Molar conductivity, elemental analysis, IR, and UV-visible spectroscopy were used to characterise these compounds. Tetrahedral complexes were generated by Schiff bases exhibiting monobasic tridentate interaction with the central Zn(II) ion. In comparison to the parent Schiff bases, these complexes were assessed for their anti-inflammatory properties and for their enhanced biological activity.