Abstract
Purpose: To synthesize new antimicrobial azo-pyrazolone derivatives III & IV and evaluate their antimicrobial activities using a combination of in vitro and molecular docking studies. Methods: Azopyrazolone compounds were prepared from the reaction of substituted aniline diazonium with ethyl acetoacetate to give azoxobutyric acid derivatives (II) which were then reacted with phenyl hydrazine or hydrazine hydrate. The pyrazolone derivatives (IV) were acetylated with glacial acetic acid to yield new acetylated pyrazolones (V). An agar dilution method was used to demonstrate the antimicrobial activities of the pyrazolone derivatives and their minimum inhibitory concentration (MIC) values calculated. Molecular docking studies were employed to further evaluate the most active compounds (on the basis of the MICs obtained). Results: The new pyrazolone derivatives showed varying antimicrobial activities (from negligible to strong) against a number of microorganisms. Derivatives IIIb and Vb showed potent activities against Bacillus subtilis, Sarcina lutea, Staphylococcus aureus and Enterococcus faecalis . However, the new compounds did not show antifungal activity. Molecular docking results for compounds IIIb and Vb were consistent with their antimicrobial activities and proved that the compounds inhibited glucosamine-6-phosphate synthase. Conclusion: The new dichloropyrazolone compounds IIIa and Vb possess potent antimicrobial activities. These compounds have promising potential for use as new antibacterial agents or as templates for the design of new antimicrobial drugs. Keywords: Azo-pyrazolone, Dichloropyrazolone, Antimicrobial, Molecular docking
Highlights
Literature survey has revealed that pyrazolone compounds exhibit a variety of biological activities [1,2,3,4,5]
In the review of reported biological activities of these derivatives, it was seen that a number of substituted phenylhydrazones bearing a pyrazole ring (IIIa-c, IVa-c and Va-c) have been synthesized (Figure 1)
To identify the possible mechanism of action of the newly synthesized compounds, they were subjected to molecular docking studies with glucosamine-6-phosphate synthase using the program of MOE site finder
Summary
Literature survey has revealed that pyrazolone compounds exhibit a variety of biological activities [1,2,3,4,5]. The azo-pyrazolone derivatives have potent cytotoxic [6,7], antiinflammatory [8,9,10] and antibacterial activities [11]. Pyrazolones 1 and 2 have antimicrobial activities and are considered novel types of non-nucleoside reverse transcriptase inhibitors against HIV-1 [12]. Drazoxolon 3 is an azo compound containing. In the review of reported biological activities of these derivatives, it was seen that a number of substituted phenylhydrazones bearing a pyrazole ring (IIIa-c, IVa-c and Va-c) have been synthesized (Figure 1).
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