Synthesis and structure activity relationship of new antibacterial active multi substituted quinoline-azetidinone mannich bases

Novel Mannich bases (Z)-2-(5-(3-chloro-2-oxo-4-p-tolylazetidin-1-yl)quinolin-8-yloxy)-N’-(2-oxo-1-(piperidin-1- ylmethyl)indolin-3-ylidine)acetohydrazides were synthesized by the condensation of 2-(5-(3-chloro-2-oxo-4-ptolylazetidin- 1-yl)quinolin-8-yloxy)acetohydrazide with Isatin afford corresponding (Z)-2-(5-(3-chloro-2-oxo-4-ptolylazetidin- 1-yl)quinolin-8-yloxy)-N’-(2-oxoindolin-3-ylidene)acetohydrazide. This was subjected to mannich reaction with cyclic secondary amines such as piperidine / morpholine / N-Methyl Piperazine in presence of formaldehyde in DMF to give corresponding Mannich bases (Z)-2-(5-(3-chloro-2-oxo-4-p-tolylazetidin-1- yl)quinolin-8-yloxy)-N’-(2-oxo-1-(piperidin-1-ylmethyl)indolin-3-ylidine)acetohydrazide in excellent yields. The structures of these newly synthesized compounds were characterized by 1H-NMR, 13C-NMR, Mass, IR and elemental analysis. The prepared compounds have been screened on some stains of bacteria and fungai.