Microwave assisted synthesis of N’-(Alkanylidene)-2-propylquinoline-4-carbohydrazide derivatives and their antimicrobial potential

BABATUNDE, L. BELLO and KING T., IYAYE and MARKUS, W. GERMANN and OLAYINKA, O. AJANI and SADE, J. OLORUNSHOLA (2017) Microwave assisted synthesis of N’-(Alkanylidene)-2-propylquinoline-4-carbohydrazide derivatives and their antimicrobial potential. In: Seventh International Conference on Advances in Applied Science and Environmental Engineering - ASEE 2017, 01-02 July, 2017, Kuala Lumpur, Malaysia.

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Abstract

The quinoline core is a benzo-fused pyridine which exhibits wide range of therapeutic potenials that have been proven to have remarkable utilities in medicinal chemistry research. Discovery of new antibacterial agents is crucial to counter the challenge of drug-resistant bacterial infections. The aim of this present study is to synthesize N’-(alkanylidene)-2-propylquinoline-4-carbohydrazide derivati ves 4a-h in order to evaluate their antimicrobial properties for possible future drug discovery. Pfitzinger synthetic approach was used herein to convert isatin to 1 which upon esterification afforded 2 which was subsequently converted to 3 by hydrazinolysis. Microwave irradiation technique has been used herein as green method to access a series of functionalized N’-(alkanylidene)-2-propylquinoline-4-carbo hydrazide derivatives 4a-h in high yields within short time. The proposed structures of synthesized targeted compounds were validated spectroscopically by IR, UV, 1H-NMR, 13C-NMR and DEPT-135 as well as through analytical data. The in vitro screening was investigated against six bacterial isolates using agar diffusion method while the minimum inhibitory concentration (MIC) was evaluated using serial dilution method. Out of all the series of 4a-h, 2-propyl-(N’-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)quinoline-4-carbohydrazide 4e emerged as the most active antimicrobial agent. This targeted quinoline motif 4e might pave way for new bioactive template from future drug development.

Item Type: Conference or Workshop Item (Paper)
Uncontrolled Keywords: Pfitzinger approach, bioactive heterocycle, quinoline, hydrazinolysis, drug design, spectroscopy.
Depositing User: Mr. John Steve
Date Deposited: 11 Mar 2019 11:31
Last Modified: 11 Mar 2019 11:31
URI: http://publications.theired.org/id/eprint/447

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