Journal of Chemical and Pharmaceutical Research (ISSN : 0975-7384)

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Original Articles: 2012 Vol: 4 Issue: 6

Synthesis, characterization and biological evaluation of multi substituted quinoline-thiazolidinone mannich bases


A series of total six novel Quinoline Schiff bases were prepared from 5-amino-8-hydroxy quinoline and substituted aldehydes. All quinoline schiff bases were refluxed with thioacetic acid in presence of anhydrous zinc chloride and solvent N,N-dimethyl formamide to afforded novel series of 4-thiazolidinone [1a-f]. Novel Mannich bases (Z)-N'-(2- oxo-1-(piperidin-1-ylmethyl)indolin-3-ylidene)-2-((5-(4-oxo-2-(4-substitutedphenyl)thiazolidin-3-yl)quinolin-8-yl) oxy)acetohydrazide were synthesized by the condensation of 2-((5-(4-oxo-2-(4-substitutedphenyl)thiazolidin-3- yl)quinolin-8-yl)oxy)acetohydrazide with Isatin afford corresponding (Z)-2-((5-(4-oxo-2-(4-substituted phenyl)thiazolidin-3-yl)quinolin-8-yl)oxy)-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 bases (Z)-N'-(2-oxo-1-(piperidin-1-ylmethyl)indolin- 3-ylidene)-2-((5-(4-oxo-2-(4-substitutedphenyl)thiazolidin-3-yl)quinolin-8-yl)oxy) 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.

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