The current study describes the synthesis of heterocycles incorporating 2-pyrazoline and 1,3-thiazol-4-one moieties. The cycloaddition of thiosemicarbazide with diverse chalcones afforded N-thiocarbamoyl pyrazolines, which then reacted with chloroacetic acid to yield 2-pyrazolinyl-1,3-thiazol-4(5H)-ones. The active methylene group at position 5 of the synthesized thiazolones increases its reactivity with aromatic aldehydes, forming the arylidene derivatives. The chemical structures of these compounds were determined through spectral and elemental analyses. Additionally, the compounds were assessed for the antibacterial effectiveness against both Gram-positive and Gram-negative bacteria, as well as against specific species of fungi.