Palladium–catalyzed Sonogashira Synthesis of Mono- And Bisalkynylated Derivatives of Quinoline-5,8-dione and their Antimicrobial Activity

Description

– Palladium–catalyzed Sonogashira Synthesis of Mono- And Bisalkynylated Derivatives of Quinoline-5,8-dione and their Antimicrobial Activity –

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Abstract

The synthesis of five mono- and five bis-alkynylated derivatives of quinoline-5,8-diones is reported. The intermediate 6,7-dibromoquinoline-5,8-dione was obtained by nitrosation of 8- hydroxyquinoline, followed by reduction and subsequent bromination and oxidation.

The coupling reaction of 6,7-dibromoquinoline-5,8-dione via palladium-catalyzed Sonogashira cross-coupling gave the alkynylated products.

The chemical structures of the products were confirmed using spectroscopic methods which include UV-visible spectrophotometry, Fourier Transform-Infrared (FT-IR) spectroscopy, 1 H and 13C-NMR spectroscopy. The antimicrobial properties of the synthesized products were determined on Escherichia Coli 1, Escherichia Coli 12,

Klebsiella Pneumonia, Pseudomonas aeruoginosa and Staphylococcus aureus using the agar-diffusion method. Results showed significant improvement in antibacterial activities compared with ampicillin and gentamycin.

Introduction

The chemistry of quinoline-5,8-dione as a functionality is a developing field because of its various biological activities.

Quinoline-5,8-dione 1, the parent functionality of a large number of medicinal compounds have been of great interest to drug researchers due to its biological functions as antifungal, antibacterial, antiparasitic and antitumor agents. 

Streptonigrin and Lavendamycin are known antibiotic, antitumor agents containing the quinoline-5,8-dione functional group. 

Since the discovery of the parent compound, many structural modifications have been carried out in search of compounds with improved biological activities. Thus, subsequent variations in the parent structure have given rise to a large number of derivatives of medicinal interest.

Substituted quinoline-5,8-diones are useful antifungicides and antibactericides whereas some of the polynuclear quinones built on the dihaloquinoline quinine scaffold are useful tuberculostatic and cytostatic substances.

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