Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F86652079%3A_____%2F22%3A00556983" target="_blank" >RIV/86652079:_____/22:00556983 - isvavai.cz</a>

Alternative codes found

RIV/00027162:_____/22:N0000026 RIV/61989592:15310/22:73618429 RIV/00216224:14110/22:00125675 RIV/62157124:16170/22:43880280 RIV/61989592:15640/22:73618429

Result on the web

<a href="https://www.mdpi.com/1422-0067/23/6/3159" target="_blank" >https://www.mdpi.com/1422-0067/23/6/3159</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/ijms23063159" target="_blank" >10.3390/ijms23063159</a>

Result language

angličtina

Original language name

Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides

Original language description

A series of eighteen 4-chlorocinnamanilides and eighteen 3,4-dichlorocinnamanilides were designed, prepared and characterized. All compounds were evaluated for their activity against gram-positive bacteria and against two mycobacterial strains. Viability on both cancer and primary mammalian cell lines was also assessed. The lipophilicity of the compounds was experimentally determined and correlated together with other physicochemical properties of the prepared derivatives with biological activity. 3,4-Dichlorocinnamanilides showed a broader spectrum of action and higher antibacterial efficacy than 4-chlorocinnamanilides however, all compounds were more effective or comparable to clinically used drugs (ampicillin, isoniazid, rifampicin). Of the thirty-six compounds, six derivatives showed submicromolar activity against Staphylococcus aureus and clinical isolates of methicillin-resistant S. aureus (MRSA). (2E)-N-[3,5-bis(trifluoromethyl)phenyl]- 3-(4-chlorophenyl)prop-2-enamide was the most potent in series 1. (2E)-N-[3,5-bis(Trifluoromethyl)phenyl]-3-(3,4-dichlorophenyl)prop-2-enamide, (2E)-3-(3,4-dichlorophenyl)-N-[3-(trifluoromethyl)phenyl]prop-2-enamide, (2E)-3-(3,4-dichloro- phenyl)-N-[4-(trifluoromethyl)phenyl]prop-2-enamide and (2E)-3-(3,4-dichlorophenyl)- N-[4-(trifluoromethoxy)phenyl]prop-2-enamide were the most active in series 2 and in addition to activity against S. aureus and MRSA were highly active against Enterococcus faecalis and vancomycin-resistant E. faecalis isolates and against fast-growing Mycobacterium smegmatis and against slow-growing M. marinum, M. tuberculosis non-hazardous test models. In addition, the last three compounds of the above-mentioned showed insignificant cytotoxicity to primary porcine monocyte-derived macrophages.

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

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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

6

Country of publishing house

CH - SWITZERLAND

Number of pages

20

Pages from-to

3159

UT code for WoS article

000775429300001

EID of the result in the Scopus database

2-s2.0-85126269076