Comparisons of Halogenated β-Nitrostyrenes as  Antimicrobial Agents

Cornell, Hugh J.; Nguyễn, Thu Hà; Nicoletti, Gina; Jackson, Neale; Hügel, Helmut

doi:10.3390/app4030380

Cited by 17 publications

(27 citation statements)

References 25 publications

(34 reference statements)

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“…Melting points and NMR data of the synthesized β-nitrostyrenes were consistent with the literature values (Gairaud and Lappin, 1953; Somasekhara et al, 1971; Bose et al, 1992; Wang and Wang, 2002; Al-Zereini et al, 2007; Yan et al, 2008; Kumar et al, 2012; Manna et al, 2013; Cornell et al, 2014). …”

Section: Resultssupporting

confidence: 88%

“…1-chloro-4-((E)-2-nitroprop-1-enyl) benzene (2) (Cornell et al, 2014 ): IR (cm −1 ): 3180, 2980, 1653, 1503, 1397, 1299, 1081, 973, 816; 1 H NMR (DMSO-D6,300 MHz): δ 2.37 (s, 3H), 7.30 (d, J = 8.4 Hz, 2H), 7.37 (d, J = 8.7 Hz, 2H), 7.97 (s, 1H); ESI-MS (m/z): 198 (M + +1); Anal. Calcd for (C 9 H 8 ClNO 2 ): C, 54.70; H, 4.08; Cl, 17.94; N, 7.09.…”

Section: Methodsmentioning

confidence: 99%

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β-Nitrostyrenes as Potential Anti-leishmanial Agents

et al. 2016

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Development of new therapeutic approach to treat leishmaniasis has become a priority. In the present study, the antileishmanial effect of β-nitrostyrenes was investigated against in vitro promastigotes and amastigotes. A series of β-nitrostyrenes have been synthesized by using Henry reaction and were evaluated for their antimicrobial activities by broth microdilution assay and in vitro antileishmanial activities against Leishmania donovani promastigotes by following standard guidelines. The most active compounds were futher evaluated for their in vitro antileishmanial activities against intracellular amastigotes. Among the tested β-nitrostyrenes, compounds 7, 8, 9, 12, and 17 exhibited potential activities (MICs range, 0.25–8 μg/mL) against clinically significant human pathogenic fungi. However, the microbactericidal concentrations (MBCs) and the microfungicidal concentrations (MFCs) were found to be either similar or only two-fold greater than the MICs. Anti-leishmanial results demonstrated that compounds 9, 12, 14, and 18 were found to be most active among the tested samples and exhibited 50% inhibitory concentration (IC50) by 23.40 ± 0.71, 37.83 ± 3.74, 40.50 ± 1.47, 55.66 ± 2.84 nM against L. donovani promastigotes and 30.5 ± 3.42, 21.46 ± 0.96, 26.43 ± 2.71, and 61.63 ± 8.02 nM respectively against intracellular L. donovani promastigotes amastigotes respectively which are comparable with standard AmB (19.60 ± 1.71 nM against promastigotes and 27.83 ± 3.26 nM against amastigotes). Compounds 9, 12, 14, and 18 were found to have potent in vitro leishmanicidal activity against L. donovani and found to be non-toxic against mammalian macrophages even at a concentration of 25 μM. Nitric oxide (NO) estimation studies reveals that these compounds are moderately inducing NO levels.

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Section: Resultssupporting

confidence: 88%

Section: Methodsmentioning

confidence: 99%

β-Nitrostyrenes as Potential Anti-leishmanial Agents

et al. 2016

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“…This compound can be usually synthesized via condensation of nitroalkanes with different aromatic aldehydes. The reaction is often catalyzed by addition of bases such as alcoholic potassium hydroxide or alcoholic methylamine or zinc chloride . Different amines were used to react with β‐nitrostyrene in acetonitrile to give the target Mannich bases.…”

Section: Resultsmentioning

confidence: 82%

“…The nitro‐antimicrobial agents, nitrofurazone and nitrofuran drugs, were the first heterocyclic nitro compound used in human medicine for its antibacterial properties . β‐Nitrostyrene and its derivatives have been screened in the literature as antimicrobial agents with excellent outcomes . Herein in the current research, we have concentrated on the synthesis of some novel nitro Mannich bases and address its antibacterial activity.…”

Section: Introductionmentioning

confidence: 99%

Novel Pyruvate Kinase (PK) Inhibitors: New Target to Overcome Bacterial Resistance

et al. 2020

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In the present investigation, some novel nitro Mannich bases derived from Michael type addition of activated nitro olefin, β‐nitrostyrene with various amines either primary or secondary including some amino sugars were designed and synthesized. The produced Mannich bases have been full characterized through different spectroscopic techniques. Antimicrobial evaluation has been performed against the Gram positive S. aureus and methicillin‐resistant S. aurues (MRSA) infections. 5 of the synthesized compounds represent the best candidates in the biological screening, they have exhibited good activity with MIC values range from 100 to 250 μg/ml. The active agents have been tested for pyruvate kinase inhibition activity with % of inhibition range from 30 to 79 % with IC50 in a nano molar range. They also exhibited significant Pyruvate kinase inhibition in nanomolar range with IC50 of 1066, 662, 1887, 418 and 1128 ng/ml, respectively (versus 196 ng/ml for AZD7545). Molecular docking calculations for active agents were performed. A complete conformational analysis molecular modeling utilizing Gaussian 09 program (HF/DFT) was used to verify the mode of bonding through the optimized geometries as well as essential quantum parameters were calculated using frontier energies (EHOMO & ELUMO) for the active candidates indicating the overall stability of the structure.

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“…(11,12) This approach does not require medication, and hence, does not generate drug resistance. (13)(14)(15)(16) Because this sterilization method is effective for treating antibiotic-resistant strains, it has been receiving increasing attention. (17,18) PDI uses a specific-wavelength LED or laser irradiation on a photosensitizer (PS).…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Photodynamic Inactivation Efficiency Using Conventional and Decorative Light-Emitting Diode Lamps

2017

Sensors and Materials

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We studied the bacterial inactivation effects of conventional and decorative light-emitting diode (LED) lamps. We used erythrosine and toluidine blue O as photosensitizers, mixed them with bacteria, painted the mixture on nutrient agar (NA), and then irradiated the NA with commercial green, red, and white LED lamps. The experimental results showed a positive photodynamic inactivation effect on Escherichia coli and Staphylococcus aureus reduction in the experiment. Thus, we demonstrated a decrease in the in vitro growth of E. coli and S. aureus by using easily available LED lamps. This experiment revealed the possibility of using conventional and decorative lighting for daily bacterial inactivation in the future.

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Comparisons of Halogenated β-Nitrostyrenes as Antimicrobial Agents

Cited by 17 publications

References 25 publications

β-Nitrostyrenes as Potential Anti-leishmanial Agents

β-Nitrostyrenes as Potential Anti-leishmanial Agents

Novel Pyruvate Kinase (PK) Inhibitors: New Target to Overcome Bacterial Resistance

Evaluation of Photodynamic Inactivation Efficiency Using Conventional and Decorative Light-Emitting Diode Lamps

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