Abstract
In this study a series of twelve n-alkoxy-substituted 2-hydroxynaphthalene-1-carboxanilides was prepared and characterized. The discussed compounds were prepared by microwave-assisted synthesis. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The highest PET inhibition was observed for meta-substituted compounds, whereas 2-hydroxy-N-(3-propoxyphenyl)naphthalene-1-carboxamide showed the highest PET inhibition within the whole series. In spite of medium or moderate PET-inhibiting activity it was found that the compounds inhibit PET in photosystem II. The activity of all positional isomers is strongly influenced by lipophilicity and the length/bulkiness of the alkoxy chain.
Highlights
Salicylanilides (N-substituted hydroxybenzamides) represent compounds with a wide range of pharmacological activities, including anti-inflammatory [1], anthelmintic [2] and antimicrobial [3,4,5,6,7,8,9] properties
At present approximately 20 mechanisms of action of herbicides are known [16], over 50% of commercially available herbicides act by reversible binding to photosystem II (PS II), a membrane-protein complex in the thylakoid membranes, which catalyses the oxidation of water and the reduction of plastoquinone [17], and thereby inhibit photosynthesis [18,19,20]
All the studied compounds were prepared according to Scheme 1
Summary
Salicylanilides (N-substituted hydroxybenzamides) represent compounds with a wide range of pharmacological activities, including anti-inflammatory [1], anthelmintic [2] and antimicrobial [3,4,5,6,7,8,9] properties. According to the results reported recently, salicylanilides and their analogues were found to be inhibitors of photosynthetic electron transport (PET). In the context of the previously-described amides/carbamates [4,5,6,7,8,9,10,11,12,13,14,15,21,22], new N-(n-alkoxy)phenylamides of 2-hydroxynaphthalene-1-carboxylic acid were prepared and tested for their photosynthesis-inhibiting activity – the inhibition of photosynthetic electron transport in spinach chloroplasts (Spinacia oleracea L.).
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