Halogenated Cinnamanilides and Their Activity Against Selected Gram-Negative Bacteria

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14110%2F25%3A00142681" target="_blank" >RIV/00216224:14110/25:00142681 - isvavai.cz</a>

Výsledek na webu

<a href="https://www.mdpi.com/2673-4583/18/1/22" target="_blank" >https://www.mdpi.com/2673-4583/18/1/22</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/ecsoc-29-26718" target="_blank" >10.3390/ecsoc-29-26718</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Halogenated Cinnamanilides and Their Activity Against Selected Gram-Negative Bacteria

Popis výsledku v původním jazyce

Recently published halogenated anilides of chlorinated and trifluorinated cinnamic acids, such as (2E)-N-[3,5-bis(trifluoromethyl)phenyl]-3-(3,4-dichlorophenyl)prop-2-enamide, (2E)-N-(3,5-dichlorophenyl)-3-[3-(trifluoromethyl)phenyl]prop-2-enamide, or (2E)-N-[3,5- bis(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)phenyl]prop-2-enamide, showed excel- lent antibacterial activities in vitro against Gram-positive bacteria, especially against refer- ence and quality control strains Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212, as well as against representatives of multidrug-resistant bacteria, clinical isolates of methicillin-resistant S. aureus (MRSA), and vancomycin-resistant E. faecalis (VRE) with minimum inhibitory concentrations (MICs) against staphylococci &lt; 0.2 μg/mL and against enterococci &lt; 4 μg/mL. It should be noted that all these compounds are rather lipophilic (software predicted log P values close to 5) and carry electron-withdrawing substituents that allow them to be classified as so-called Michael acceptors. All these facts inspired further investigation of the spectrum of effectiveness against other bacteria, and the most effective agents with various substitutions in both the anilide part and on the phenyl ring of the parent cinnamic acid were chosen and tested against selected pathogenic Gram-negative bacteria, such as reference and quality control strains Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27859, and a clinical isolate of Klebsiella pneumoniae 797. Unfortunately, it was found that none of the selected halogenated anilide derivatives with such high potency against Gram-positive bacteria demonstrated better efficacy against the tested Gram-negative bacteria than a MIC of 256 μg/mL.

Název v anglickém jazyce

Halogenated Cinnamanilides and Their Activity Against Selected Gram-Negative Bacteria

Popis výsledku anglicky

Recently published halogenated anilides of chlorinated and trifluorinated cinnamic acids, such as (2E)-N-[3,5-bis(trifluoromethyl)phenyl]-3-(3,4-dichlorophenyl)prop-2-enamide, (2E)-N-(3,5-dichlorophenyl)-3-[3-(trifluoromethyl)phenyl]prop-2-enamide, or (2E)-N-[3,5- bis(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)phenyl]prop-2-enamide, showed excel- lent antibacterial activities in vitro against Gram-positive bacteria, especially against refer- ence and quality control strains Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212, as well as against representatives of multidrug-resistant bacteria, clinical isolates of methicillin-resistant S. aureus (MRSA), and vancomycin-resistant E. faecalis (VRE) with minimum inhibitory concentrations (MICs) against staphylococci &lt; 0.2 μg/mL and against enterococci &lt; 4 μg/mL. It should be noted that all these compounds are rather lipophilic (software predicted log P values close to 5) and carry electron-withdrawing substituents that allow them to be classified as so-called Michael acceptors. All these facts inspired further investigation of the spectrum of effectiveness against other bacteria, and the most effective agents with various substitutions in both the anilide part and on the phenyl ring of the parent cinnamic acid were chosen and tested against selected pathogenic Gram-negative bacteria, such as reference and quality control strains Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27859, and a clinical isolate of Klebsiella pneumoniae 797. Unfortunately, it was found that none of the selected halogenated anilide derivatives with such high potency against Gram-positive bacteria demonstrated better efficacy against the tested Gram-negative bacteria than a MIC of 256 μg/mL.

Druh

D - Stať ve sborníku

CEP obor

—

OECD FORD obor

30107 - Medicinal chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název statě ve sborníku

Halogenated Cinnamanilides and Their Activity against Selected Gram-negative Bacteria

ISBN

—

ISSN

2673-4583

e-ISSN

—

Počet stran výsledku

7

Strana od-do

1-7

Název nakladatele

MDPI

Místo vydání

ECSOC-29

Místo konání akce

ECSOC-29

Datum konání akce

14. 11. 2025

Typ akce podle státní příslušnosti

WRD - Celosvětová akce

Kód UT WoS článku

—