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

Article in a journal

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

Switzerland

Confidentiality degree

is not subject to a state or trade secret

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

EID Scopus

2-s2.0-85111292238

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.

Cite

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.

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