Antimicrobial and ADME properties of methoxylated, methylated and nitrated 2-hydroxynaphthalene-1 carboxanilide

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F86652079%3A_____%2F25%3A00618735" target="_blank" >RIV/86652079:_____/25:00618735 - isvavai.cz</a>

Result on the web

<a href="https://pub.iapchem.org/ojs/index.php/admet/article/view/2642" target="_blank" >https://pub.iapchem.org/ojs/index.php/admet/article/view/2642</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.5599/admet.2642" target="_blank" >10.5599/admet.2642</a>

Result language

angličtina

Original language name

Antimicrobial and ADME properties of methoxylated, methylated and nitrated 2-hydroxynaphthalene-1 carboxanilide

Original language description

Many new compounds are being prepared to overcome the problem of increasing microbial resistance and the increasing number of infections. Experimental approach:This study includes a series of twenty-seven mono-, di-and trisubstituted 2-hydroxynaphthalene-1-carboxanilides designed as multitarget agents. The compounds are substituted with methoxy, methyl, and nitro groups, as well as additionally with chlorine, bromine, and trifluoromethyl at various positions. All the compounds wereevaluated for antibacterial activities against Gram-positive and Gram-negative bacteria and mycobacteria. Cytotoxicity on human cells was also tested. Key results:Three compounds showed activity comparable to clinically used drugs. N-(3,5-Dimethylphenyl)-2-hydroxynaphthalene-1-carboxamide (13) showed only antista-phylococcal activity (minimum inhibitory concentration(MIC) = 54.9μM), 2-hydroxy-N-[2-methyl-5-(trifluoro-methyl)phenyl]naphthalene-1-carboxamide(22) and 2-hydroxy-N-[4-nitro-3-(trifluoromethyl)phenyl]naphtha-lene-1-carboxamide(27) were active across the entire spectrum of tested bacteria/mycobacteria, both against the sensitive set and against resistant isolates (MICs range 0.3 to 92.6μM). Compound 22was even active against E. coli(MIC = 23.2μM). The active agents showed no in vitrocytotoxicity up to a concentration of 30 μM. Conclusion:Compounds with trifluoromethyl in the meta-anilideposition, experimental lipophilicity expressed as log k(logarithm of the capacity factor) in the range of 0.31 to 0.34 and calculated electron σ parameter for the anilide substituent higher than 0.59 were effective. The investigated compounds meet the definition of Michael acceptors. Based on ADME screening, the investigated compounds 13, 22and 27should have suitable physicochemical parameters for good bioavailability in the organism. Therefore, these are promising agentsfor further study.

Czech name

—

Czech description

—

Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

30104 - Pharmacology and pharmacy

Project

<a href="/en/project/LM2023048" target="_blank" >LM2023048: Czech Carbon Observation System</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2025

Confidentiality

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

Name of the periodical

ADMET and DMPK

ISSN

1848-7718

e-ISSN

1848-7718

Volume of the periodical

13

Issue of the periodical within the volume

1

Country of publishing house

HR - CROATIA

Number of pages

21

Pages from-to

2642

UT code for WoS article

001422088100001

EID of the result in the Scopus database

2-s2.0-105001719341