Detailed Information on Publication Record
2019
Activity of N-Phenylpiperazine Derivatives Against Bacterial and Fungal Pathogens
POSPÍŠILOVÁ, Šárka, Pavlína MARVANOVÁ, Jakub TREML, Agnes M. MORICZ, Peter G. OTT et. al.Basic information
Original name
Activity of N-Phenylpiperazine Derivatives Against Bacterial and Fungal Pathogens
Authors
POSPÍŠILOVÁ, Šárka (203 Czech Republic), Pavlína MARVANOVÁ (203 Czech Republic), Jakub TREML (203 Czech Republic), Agnes M. MORICZ (348 Hungary), Peter G. OTT (348 Hungary), Petr MOKRÝ (203 Czech Republic), Klára ODEHNALOVÁ (203 Czech Republic), Ondrej ŠEDO (203 Czech Republic, guarantor, belonging to the institution), Alois ČÍŽEK (203 Czech Republic) and Josef JAMPÍLEK (203 Czech Republic)
Edition
CURRENT PROTEIN & PEPTIDE SCIENCE, Bentham Science Publishers, 2019, 1389-2037
Other information
Language
English
Type of outcome
Článek v odborném periodiku
Field of Study
10608 Biochemistry and molecular biology
Country of publisher
United States of America
Confidentiality degree
není předmětem státního či obchodního tajemství
References:
Impact factor
Impact factor: 2.520
RIV identification code
RIV/00216224:14740/19:00107988
Organization unit
Central European Institute of Technology
UT WoS
000492730400011
Keywords in English
N-phenylpiperazines; synthesis; lipophilicity; dissociation constant; antimycobacterials; antifungals; cytotoxicity
Tags
International impact, Reviewed
Změněno: 2/11/2024 20:21, Ing. Martina Blahová
Abstract
V originále
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.
Links
| GBP206/12/G151, research and development project |
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| LQ1601, research and development project |
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| 90043, large research infrastructures |
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