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

J 2022

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

STRHARSKY, Tomas; Dominika PINDJAKOVA; Jiří KOS; Lucia VRABLOVA; Hana MICHNOVA et al.

Základní údaje

Originální název

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

Autoři

STRHARSKY, Tomas; Dominika PINDJAKOVA; Jiří KOS; Lucia VRABLOVA; Hana MICHNOVA; Jan HOSEK; Nicol STRAKOVA; Veronika LELAKOVA; Lenka LEVA; Lenka KAVANOVA; Michal ORAVEC; Alois CIZEK a Josef JAMPILEK

Vydání

International Journal of Molecular Sciences, Basel, MDPI, 2022, 1422-0067

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10608 Biochemistry and molecular biology

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14110/22:00125675

Organizační jednotka

Lékařská fakulta

Klíčová slova anglicky

cinnamamides; antimicrobial activity; cytotoxicity; lipophilicity; structure-activity relationships

Štítky

14110512, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 19. 4. 2022 09:25, Mgr. Tereza Miškechová

Anotace

V originále

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.

Návaznosti

90123, velká výzkumná infrastruktura

Název: CzeCOS III

Citovat

STRHARSKY, Tomas; Dominika PINDJAKOVA; Jiří KOS; Lucia VRABLOVA; Hana MICHNOVA; Jan HOSEK; Nicol STRAKOVA; Veronika LELAKOVA; Lenka LEVA; Lenka KAVANOVA; Michal ORAVEC; Alois CIZEK a Josef JAMPILEK. Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides. International Journal of Molecular Sciences. Basel: MDPI, 2022, roč. 23, č. 6, s. 1-20. ISSN 1422-0067. Dostupné z: https://doi.org/10.3390/ijms23063159.

@article{1847637,
   author = {Strharsky, Tomas and Pindjakova, Dominika and Kos, Jiří and Vrablova, Lucia and Michnova, Hana and Hosek, Jan and Strakova, Nicol and Lelakova, Veronika and Leva, Lenka and Kavanova, Lenka and Oravec, Michal and Cizek, Alois and Jampilek, Josef},
   article_location = {Basel},
   article_number = {6},
   doi = {https://doi.org/10.3390/ijms23063159},
   keywords = {cinnamamides; antimicrobial activity; cytotoxicity; lipophilicity; structure-activity relationships},
   language = {eng},
   issn = {1422-0067},
   journal = {International Journal of Molecular Sciences},
   title = {Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides},
   url = {https://www.mdpi.com/1422-0067/23/6/3159},
   volume = {23},
   year = {2022}
}

TY  - JOUR
ID  - 1847637
AU  - Strharsky, Tomas - Pindjakova, Dominika - Kos, Jiří - Vrablova, Lucia - Michnova, Hana - Hosek, Jan - Strakova, Nicol - Lelakova, Veronika - Leva, Lenka - Kavanova, Lenka - Oravec, Michal - Cizek, Alois - Jampilek, Josef
PY  - 2022
TI  - Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides
JF  - International Journal of Molecular Sciences
VL  - 23
IS  - 6
SP  - 1-20
EP  - 1-20
PB  - MDPI
SN  - 14220067
KW  - cinnamamides
KW  - antimicrobial activity
KW  - cytotoxicity
KW  - lipophilicity
KW  - structure-activity relationships
UR  - https://www.mdpi.com/1422-0067/23/6/3159
N2  - 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.
ER  -

STRHARSKY, Tomas; Dominika PINDJAKOVA; Jiří KOS; Lucia VRABLOVA; Hana MICHNOVA; Jan HOSEK; Nicol STRAKOVA; Veronika LELAKOVA; Lenka LEVA; Lenka KAVANOVA; Michal ORAVEC; Alois CIZEK a Josef JAMPILEK. Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides. \textit{International Journal of Molecular Sciences}. Basel: MDPI, 2022, roč.~23, č.~6, s.~1-20. ISSN~1422-0067. Dostupné z: https://doi.org/10.3390/ijms23063159.

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