The reaction of 5-acetyl-8-quinolinol (1) and corresponding chalcone derivatives 2a–f with hydroxylamine hydrochloride in boiling pyridine gave the corresponding oximes 3 and 4a–f respectively in almost quantitative yields. Further interaction of 3 and 4a–e with phenyl isocyanate and/or thiocyanate the corresponding carbamate and/or thiocarbamate (5a,b) and (6a–e, 7a–e) were achieved. Metal chelates of 1, 3, and 4e,f with bivalent metal cations like Fe(II), Cu(II), and Zn(II) have been synthesized and characterized by elemental and IR-spectral analysis. The synthesized compounds were biologically screened to study the structure activity relationship, (SAR) and the effect of complexation and type of metal cation on the potency of the more biologically active compounds