Photosynthesis-Inhibiting Activity of
N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides

J 2021

Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides

KOS, Jiří, Tomáš GONĚC, Michal ORAVEC, Izabela JENDRZEJEWSKA, Josef JAMPÍLEK et. al.

Základní údaje

Originální název

Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides

Autoři

KOS, Jiří (203 Česká republika, garant, domácí), Tomáš GONĚC (203 Česká republika, domácí), Michal ORAVEC (203 Česká republika), Izabela JENDRZEJEWSKA (616 Polsko) a Josef JAMPÍLEK (703 Slovensko)

Vydání

Molecules, MDPI Basel, 2021, 1420-3049

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

30104 Pharmacology and pharmacy

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

Odkaz na plný text výsledku nebo domovskou stránku výsledku.

Impakt faktor

Impact factor: 4.927

Kód RIV

RIV/00216224:14160/21:00122029

Organizační jednotka

Farmaceutická fakulta

DOI

http://dx.doi.org/10.3390/molecules26144336

UT WoS

000676741300001

Klíčová slova anglicky

hydroxynaphthalene-carboxamides; PET inhibition; spinach chloroplasts; structure-activity relationships

Štítky

14110512, podil, rivok, ÚChL

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 22. 4. 2022 09:53, PharmDr. Tomáš Goněc, Ph.D.

Anotace

V originále

A set of twenty-four 3-hydroxynaphthalene-2-carboxanilides, disubstituted on the anilide ring by combinations of methoxy/methyl/fluoro/chloro/bromo and ditrifluoromethyl groups at different positions, was prepared. The compounds were tested for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3,5-Difluorophenyl)-, N-(3,5-dimethylphenyl)-, N-(2,5-difluorophenyl)- and N-(2,5-dimethylphenyl)-3-hydroxynaphthalene-2-carboxamides showed the highest PET-inhibiting activity (IC50 similar to 10 mu M) within the series. These compounds were able to inhibit PET in photosystem II. It has been found that PET-inhibiting activity strongly depends on the position of the individual substituents on the anilide ring and on the lipophilicity of the compounds. The electron-withdrawing properties of the substituents contribute towards the PET activity of these compounds.

Citovat

KOS, Jiří, Tomáš GONĚC, Michal ORAVEC, Izabela JENDRZEJEWSKA a Josef JAMPÍLEK. Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides. Molecules. MDPI Basel, 2021, roč. 26, č. 14, s. 1-9. ISSN 1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules26144336.

@article{1784759,
   author = {Kos, Jiří and Goněc, Tomáš and Oravec, Michal and Jendrzejewska, Izabela and Jampílek, Josef},
   article_number = {14},
   doi = {http://dx.doi.org/10.3390/molecules26144336},
   keywords = {hydroxynaphthalene-carboxamides; PET inhibition; spinach chloroplasts; structure-activity relationships},
   language = {eng},
   issn = {1420-3049},
   journal = {Molecules},
   title = {Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides},
   url = {https://www.mdpi.com/1420-3049/26/14/4336},
   volume = {26},
   year = {2021}
}

TY  - JOUR
ID  - 1784759
AU  - Kos, Jiří - Goněc, Tomáš - Oravec, Michal - Jendrzejewska, Izabela - Jampílek, Josef
PY  - 2021
TI  - Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides
JF  - Molecules
VL  - 26
IS  - 14
SP  - 1-9
EP  - 1-9
PB  - MDPI Basel
SN  - 14203049
KW  - hydroxynaphthalene-carboxamides
KW  - PET inhibition
KW  - spinach chloroplasts
KW  - structure-activity relationships
UR  - https://www.mdpi.com/1420-3049/26/14/4336
N2  - A set of twenty-four 3-hydroxynaphthalene-2-carboxanilides, disubstituted on the anilide ring by combinations of methoxy/methyl/fluoro/chloro/bromo and ditrifluoromethyl groups at different positions, was prepared. The compounds were tested for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3,5-Difluorophenyl)-, N-(3,5-dimethylphenyl)-, N-(2,5-difluorophenyl)- and N-(2,5-dimethylphenyl)-3-hydroxynaphthalene-2-carboxamides showed the highest PET-inhibiting activity (IC50 similar to 10 mu M) within the series. These compounds were able to inhibit PET in photosystem II. It has been found that PET-inhibiting activity strongly depends on the position of the individual substituents on the anilide ring and on the lipophilicity of the compounds. The electron-withdrawing properties of the substituents contribute towards the PET activity of these compounds.
ER  -

KOS, Jiří, Tomáš GONĚC, Michal ORAVEC, Izabela JENDRZEJEWSKA a Josef JAMPÍLEK. Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides. \textit{Molecules}. MDPI Basel, 2021, roč.~26, č.~14, s.~1-9. ISSN~1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules26144336.

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