Synthesis and Antimicrobial Activity of Nitroalkenyl Arenes

Nicoletti, Gina; Cornell, Hugh J.; Hügel, Helmut; White, Kylie; Nguyễn, Thu Hà; Zalizniak, Liliana; Nugegoda, Dayanthi

doi:10.2174/2211352511311020012

Cited by 9 publications

(33 citation statements)

References 1 publication

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“…This compound has been evaluated in different assays, and the results in Table 3 are from an assay in which I was evaluated against 4-fluoro-β-nitrostyrene (without the β-methyl group), which showed that I was much better than 4-fluoro-β-nitrostyrene and also A-1. In all of our work, we have found this to be the case (see [12,13]). Table 1 shows the MICs in μg mL −1 of β-nitrostyrene analogues tested against four strains of bacteria and a fungus.…”

Section: Analysis Of Assayssupporting

confidence: 51%

“…Three assays, as previously described [12,13], were used to determine the antibacterial efficacy of the β-nitrostyrenes by their activity against a panel of 4 bacteria and a fungus (Candida albicans). The results appear as the minimum inhibitory concentration (MIC) for each compound and are presented in the Tables 1 and 2 The three assays were performed as follows: Assay 1.…”

Section: Methodsmentioning

confidence: 99%

“…3,4-Methylenedioxy-β-methyl-β-nitrostyrene (A-1) was prepared by piperidine-catalysed condensation of piperonal with nitroethane, as previously described [13].…”

Section: Methodsmentioning

confidence: 99%

“…Our previous research on the structure activity relationships (SARs) of nitrostyrene derivatives for antibacterial activity revealed that the presence of a fluorine atom at the para position on the benzene ring showed the highest activity against Gram-negative bacteria [12,13]. The aim of the present research work is to study the effect of various halogen substitutions at different ring and side chain positions of β-nitrostyrene derivatives on antibacterial activity.…”

Section: Introductionmentioning

confidence: 97%

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Comparisons of Halogenated β-Nitrostyrenes as Antimicrobial Agents

et al. 2014

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Abstract:The influence of three types of halogen-substituted E-β-methyl-β-nitrostyrenes (such as Compounds B, D, H) to overcome bacterial activity that is currently a significant health threat was studied. The evaluations of their bio-potency was measured and related to their structure and activity relationships for the purposes of serving to inhibit and overcoming resistant microorganisms. In particular, fluorine-containing β-nitrostyrenes were found to be highly active antimicrobial agents. The addition of the β-bromo group enhanced the antibacterial activity significantly. Our work has illustrated that halogen substituents at both the 4-position in the aromatic ring and also at the β-position on the alkene side chain of nitropropenyl arenes enhanced the antimicrobial activity of these compounds.

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Section: Analysis Of Assayssupporting

confidence: 51%

Section: Methodsmentioning

confidence: 99%

“…3,4-Methylenedioxy-β-methyl-β-nitrostyrene (A-1) was prepared by piperidine-catalysed condensation of piperonal with nitroethane, as previously described [13].…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

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Comparisons of Halogenated β-Nitrostyrenes as Antimicrobial Agents

et al. 2014

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“…The antimicrobial activity of a range of β-methyl-β-nitrostyrene derivatives 4 against Gram positive, Gram negative bacteria and fungi were evaluated by Nicoletti et al [14] who had previously found that:…”

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confidence: 99%

A Study of Fluorinated β-Nitrostyrenes as Antimicrobial Agents

Cornell

Nicoletti

et al. 2012

Applied Sciences

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Abstract:The effect of variously fluorine-substituted β-methyl-β-nitrostyrenes on their antimicrobial activity was investigated. Their efficacy was determined by minimum inhibition concentration (MIC) in cultures of Gram positive and Gram negative bacteria and a fungus. Highest activity against the Gram negative bacterium, E.coli, was achieved with 4-fluorine-aryl substituted β-methyl-β-nitrostyrenes, while most compounds gave excellent results against gram positive bacteria. Importantly, the addition of the β-methyl group profoundly enhanced the antibacterial activity of the compounds tested. The comparative K D values for the most potent compounds against E.coli were much lower than those required for the gram positive and fungus counterparts. This investigation illustrated that fluorine substituted nitropropenylarenes have enhanced antimicrobial activity suitable for antibiotic applications.

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