Trifluoromethylcinnamanilide Michael Acceptors for Treatment of Resistant Bacterial Infections

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F86652079%3A_____%2F22%3A00566362" target="_blank" >RIV/86652079:_____/22:00566362 - isvavai.cz</a>

Alternative codes found

RIV/00027162:_____/22:N0000184 RIV/00216224:14110/22:00127694 RIV/62157124:16170/22:43880276

Result on the web

<a href="https://www.mdpi.com/1422-0067/23/23/15090" target="_blank" >https://www.mdpi.com/1422-0067/23/23/15090</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/ijms232315090" target="_blank" >10.3390/ijms232315090</a>

Result language

angličtina

Original language name

Trifluoromethylcinnamanilide Michael Acceptors for Treatment of Resistant Bacterial Infections

Original language description

A series of thirty-two anilides of 3-(trifluoromethyl)cinnamic acid (series 1) and 4-(trifluoromethyl)cinnamic acid (series 2) was prepared by microwave-assisted synthesis. All the compounds were tested against reference strains Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 and resistant clinical isolates of methicillin-resistant S. aureus (MRSA) and vancomycin-resistant E. faecalis (VRE). All the compounds were evaluated in vitro against Mycobacterium smegmatis ATCC 700084 and M. marinum CAMP 5644. (2E)-3-[3-(Trifluoromethyl)phenyl]-N-[4-(trifluoromethyl)phenyl]prop-2-enamide (1j), (2E)-N-(3,5-dichlorophenyl)-3-[3-(trifluoromethyl)phenyl]prop-2-enamide (1o) and (2E)-N-[3-(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)-phenyl]prop-2-enamide (2i), (2E)-N-[3,5-bis(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)phenyl]-prop-2-enamide (2p) showed antistaphylococcal (MICs/MBCs 0.15-5.57 mu M) as well as anti-enterococcal (MICs/MBCs 2.34-44.5 mu M) activity. The growth of M. marinum was strongly inhibited by compounds 1j and 2p in a MIC range from 0.29 to 2.34 mu M, while all the agents of series 1 showed activity against M. smegnatis (MICs ranged from 9.36 to 51.7 mu M). The performed docking study demonstrated the ability of the compounds to bind to the active site of the mycobacterial enzyme InhA. The compounds had a significant effect on the inhibition of bacterial respiration, as demonstrated by the MTT assay. The compounds showed not only bacteriostatic activity but also bactericidal activity. Preliminary in vitro cytotoxicity screening was assessed using the human monocytic leukemia cell line THP-1 and, except for compound 2p, all effective agents did show insignificant cytotoxic effect. Compound 2p is an interesting anti-invasive agent with dual (cytotoxic and antibacterial) activity, while compounds 1j and 1o are the most interesting purely antibacterial compounds within the prepared molecules.

Czech name

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Czech description

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Type

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

CEP classification

—

OECD FORD branch

10608 - Biochemistry and molecular biology

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2022

Confidentiality

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

Name of the periodical

International Journal of Molecular Sciences

ISSN

1422-0067

e-ISSN

1422-0067

Volume of the periodical

23

Issue of the periodical within the volume

23

Country of publishing house

CH - SWITZERLAND

Number of pages

22

Pages from-to

15090

UT code for WoS article

000897240400001

EID of the result in the Scopus database

2-s2.0-85143746002