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.

Basic information

Original name

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

Authors

KOS, Jiří (203 Czech Republic, guarantor, belonging to the institution), Tomáš GONĚC (203 Czech Republic, belonging to the institution), Michal ORAVEC (203 Czech Republic), Izabela JENDRZEJEWSKA (616 Poland) and Josef JAMPÍLEK (703 Slovakia)

Edition

Molecules, MDPI Basel, 2021, 1420-3049

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

Switzerland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

Odkaz na plný text výsledku nebo domovskou stránku výsledku.

Impact factor

Impact factor: 4.927

RIV identification code

RIV/00216224:14160/21:00122029

Organization unit

Faculty of Pharmacy

DOI

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

UT WoS

000676741300001

Keywords in English

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

Abstract

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 and Josef JAMPÍLEK. Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides. Molecules. MDPI Basel, 2021, vol. 26, No 14, p. 1-9. ISSN 1420-3049. Available from: 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 and Josef JAMPÍLEK. Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides. \textit{Molecules}. MDPI Basel, 2021, vol.~26, No~14, p.~1-9. ISSN~1420-3049. Available from: https://dx.doi.org/10.3390/molecules26144336.

Detailed Information on Publication Record