Activity of N-Phenylpiperazine Derivatives Against Bacterial and Fungal Pathogens
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62157124%3A16170%2F19%3A43877847" target="_blank" >RIV/62157124:16170/19:43877847 - isvavai.cz</a>
Alternative codes found
RIV/00216224:14740/19:00107988 RIV/61989592:15310/19:73596649 RIV/62157124:16370/19:43877847
Result on the web
<a href="https://doi.org/10.2174/1389203720666190913114041" target="_blank" >https://doi.org/10.2174/1389203720666190913114041</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.2174/1389203720666190913114041" target="_blank" >10.2174/1389203720666190913114041</a>
Alternative languages
Result language
angličtina
Original language name
Activity of N-Phenylpiperazine Derivatives Against Bacterial and Fungal Pathogens
Original language description
Background: As the bacterial resistance to antibacterial chemotherapeutics is one of the greatest problems in modern medicine, efforts are made to develop new antimicrobial drugs. Compounds with a piperazine ring have proved to be promising agents against various pathogens. Objective: The aim of the study was to prepare a series of new N-phenylpiperazines and determine their activity against various pathogens. Method: Target compounds were prepared by multi-step synthesis starting from an appropriate substituted acid to an oxirane intermediate reacting with 1-(4-nitrophenyl)piperazine. Lipophilicity and pK(a) values were experimentally determined. Other molecular parameters were calculated. The inhibitory activity of the target compounds against Staphylococcus aureus, four mycobacteria strains, Bipolaris sorokiniana, and Fusarium avenaceum was tested. In vitro antiproliferative activity was determined on a THP-1 cell line, and toxicity against plant was determined using Nicotiana tabacum. Results: In general, most compounds demonstrated only moderate effects. 1-(2-Hydroxy-3-{[4-(propan-2-yloxy)benzoyl]oxy}propyl)-4-(4-nitropbenyl)piperazinediium dichloride and 1-{3-[(4-butoxybenzoyl)-oxy]-2-hydroxypropyl} -4-(4-nitrophenyl)piperazinediium dichloride showed the highest inhibition activity against M. kansasii (MIC - 15.4 and 15.0 mu M, respectively) and the latter also against M. marinum (MIC = 15.0 mu M). 1-(2-Hydroxy-3-{[4-(2-propoxyethoxy)benzoyl]oxy}propyl)-4-(4-nitrophenyl)piperazinediium dichloride had the highest activity against F. avenaceum (MIC - 14.2 mu M). All the compounds showed only insignificant toxic effects on human and plant cells. Conclusion: Ten new 1-(4-nitrophenyl)piperazine derivatives were prepared and analyzed, and their antistaphylococcal, antimycobacterial, and antifungal activities were determined. The activity against M. kansasii was positively influenced by higher lipophilicity, the electron-donor properties of substituent R and a lower dissociation constant. The exact mechanism of action will be investigated in follow-up studies.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
30107 - Medicinal chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Current protein & peptide science
ISSN
1389-2037
e-ISSN
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Volume of the periodical
20
Issue of the periodical within the volume
11
Country of publishing house
AE - UNITED ARAB EMIRATES
Number of pages
11
Pages from-to
1119-1129
UT code for WoS article
000492730400011
EID of the result in the Scopus database
2-s2.0-85074379906