The structure-antimicrobial activity relationships of a promising class of the compounds containing the N-arylpiperazine scaffold

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62157124%3A16170%2F16%3A43874557" target="_blank" >RIV/62157124:16170/16:43874557 - isvavai.cz</a>

Alternative codes found

RIV/62157124:16370/16:43874557

Result on the web

<a href="http://dx.doi.org/10.3390/molecules21101274" target="_blank" >http://dx.doi.org/10.3390/molecules21101274</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/molecules21101274" target="_blank" >10.3390/molecules21101274</a>

Result language

angličtina

Original language name

The structure-antimicrobial activity relationships of a promising class of the compounds containing the N-arylpiperazine scaffold

Original language description

This research was focused on in silico characterization and in vitro biological testing of the series of the compounds carrying a N-arylpiperazine moiety. The in silico investigation was based on the prediction of electronic, steric and lipohydrophilic features. The molecules were screened against Mycobacterium avium subsp. paratuberculosis CIT03, M. smegmatis ATCC 700084, M. kansasii DSM 44162, M. marinum CAMP 5644, Staphylococcus aureus ATCC 29213, methicillin-resistant S. aureus 63718, Escherichia coli ATCC 25922, Enterococcus faecalis ATCC 29212, Candida albicans CCM 8261, C. parapsilosis CCM 8260 and C. krusei CCM 8271, respectively, by standardized microdilution methods. The eventual antiproliferative (cytotoxic) impact of those compounds was examined on a human monocytic leukemia THP-1 cell line, as a part of the biological study. Promising potential against M. kansasii was found for 1-[3-(3-ethoxyphenylcarbamoyl)oxy-2-hydroxypropyl]-4-(3-trifluoromethylphenyl)piperazin-1-ium chloride (MIC = 31.75 ?M), which was comparable to the activity of isoniazid (INH; MIC = 29.17 ?M). Moreover, 1-{2-hydroxy-3-(3-methoxyphenylcarbamoyl)oxy)propyl}-4-(4-fluorophenyl)piperazin-1-ium chloride was even more effective (MIC = 17.62 ?M) against given mycobacterium. Among the tested N-arylpiperazines, 1-{2-hydroxy-3-(4-methoxyphenylcarbamoyl)oxy)propyl}-4-(3-trifluoromethylphenyl)piperazin-1-ium chloride was the most efficient against M. marinum (MIC = 65.32 ?M). One of the common features of all investigated substances was their insignificant antiproliferative (i.e., non-cytotoxic) effect. The study discussed structure-antimicrobial activity relationships considering electronic, steric and lipophilic properties. (C) 2016 by the authors; licensee MDPI.

Czech name

—

Czech description

—

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

FR - Pharmacology and apothecary chemistry

OECD FORD branch

—

Project

—

Continuities

V - Vyzkumna aktivita podporovana z jinych verejnych zdroju

Publication year

2016

Confidentiality

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

Name of the periodical

Molecules

ISSN

1420-3049

e-ISSN

—

Volume of the periodical

21

Issue of the periodical within the volume

10

Country of publishing house

CH - SWITZERLAND

Number of pages

25

Pages from-to

—

UT code for WoS article

000389917900011

EID of the result in the Scopus database

—