Sat, 16 Dec 2017

Synthesis, QSAR and Antibacterial Activity of Some Novel Azetidinone Containing Quinoline Derivatives

M. Nagendra Babu1*, N. Pramod1, P. Amrutha1, D. Kanchana1, G.Mahaboob Basha1,C. Gopinath1

1. Annamacharya College of Pharmacy, Department of Pharmaceutical Chemistry, Rajampet, Kadapa District, Andhra Pradesh, India.


ABSTRACT

The synthesis of novel azetidinone containing quinoline derivatives involves, cyclization reaction to form quinoline-3-carbaldehyde followed by Schiff’s base formation and finally resulted into azetidinone derivatives as target molecules. Firstly, quinoline-3-carbaldehyde was prepared from N-phenylacetamide with POCl3 in dimethyl formamide (Vilsmeyer Hacck reagent) under reflux through cyclization. The formed quinoline derivative was treated with substituted aromatic amines in presence of glacial acetic acid through grindstone process to get Schiff’s bases of quinoline derivatives. Finally, these Schiff’s bases were allowed to react with acetyl chloride and triethyl amine in presence of dimethyl formamide under reflux to achieve azetidinone ring formation resulting in the novel azetidinone containing quinoline derivatives. The synthesized compounds were identified by melting point and TLC as well as characterized by IR spectroscopy. The titled compounds were screened for antibacterial activity using agar well diffusion method against Staphylococcus aureus, Escherichia coli. Most of the compounds showed good antibacterial activity against G(-)ve bacteria and mild activity against G(+)ve bacteria when compared to the standard, Amoxicillin. QSAR study was performed, results revealed that the target molecules possess higher logP values which indicates that the physicochemical parameters proportional to the biological activity. Due to its high logP value the target molecules may possess CNS activities.

Keywords: Vilsmeyer Hacck reagent, quinoline derivatives, azetidinones, antibacterial activities.


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