期刊
MOLECULES
卷 26, 期 14, 页码 -出版社
MDPI
DOI: 10.3390/molecules26144336
关键词
hydroxynaphthalene-carboxamides; PET inhibition; spinach chloroplasts; structure-activity relationships
资金
- Slovak Research and Development Agency [APVV-17-0373, APVV-17-0318]
- Ministry of Education, Youth and Sports of the Czech Republic within the CzeCOS program [LM2018123, CZ.02.1.01/0.0/0.0/16_019/0000797]
By modulating the position of substituents on the anilide ring and the lipophilicity of the compounds, the PET-inhibiting activity of the compounds can be enhanced.
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.
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