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. 2015 Apr;23(2):202-9.
doi: 10.1016/j.jsps.2014.07.009. Epub 2014 Jul 28.

Design, synthesis and antibacterial potential of 5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-1-substituted-4,5-dihydropyrazoles

Mohammed F El-Behairy  1 , Tarek E Mazeed  2 , Aida A El-Azzouny  1 , Mohamed N Aboul-Enein  1
Affiliations

Design, synthesis and antibacterial potential of 5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-1-substituted-4,5-dihydropyrazoles

Mohammed F El-Behairy et al. Saudi Pharm J. 2015 Apr.

Abstract

A series of 5-(benzo[d][1,3]dioxol-5-yl)-3-tert-butyl-1-substituted-4,5-dihydropyrazole derivatives 4a-e and 6a-g have been synthesized and spectrally characterized. The antibacterial activity of the novel candidates has been screened using the agar diffusion test. These compounds were endowed with high antibacterial activity against different Gram +ve and Gram -ve bacteria when compared with standard antibacterial drugs. In the light of zone of inhibition and MIC results, Sarcina and Staphylococcus aureus are the most sensitive bacteria where pyrrolidinomethanone derivative 4e showed MICs at 80 and 110 nM, respectively. While hydroxypiperidinoethanone derivative 6c showed MIC at 90 nM for Sarcina.

Keywords: 1,3-Benzodioxole; 2-Pyrazoline; Antibacterial.

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Figures

Figure 1
Figure 1
Antimicrobial candidates containing 1,3-benzodioxol system.
Figure 2
Figure 2
Antimicrobial candidates containing pyrazoline-methanone and ethanone scaffolds.
Figure 3
Figure 3
Pharmacophoric similarity between β-lactams and the expected metabolic products.
Scheme 1
Scheme 1
Reagents and conditions: (i) CH2Cl2, K2CO3, DMF, reflux, 4 h; (ii) pinacolone 50% KOH, CH3OH, 70 °C, 5 h; (iii) H2N–NH2·H2O, ethanol, reflux, 2 h;
Scheme 2
Scheme 2
See this image and copyright information in PMC

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