Publication details
Antimycobacterial N-alkoxyphenylhydroxynaphthalenecarboxamides affecting photosystem II
| Authors | |
|---|---|
| Year of publication | 2017 |
| Type | Article in Periodical |
| Magazine / Source | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS |
| Citation | |
| Doi | http://dx.doi.org/10.1016/j.bmcl.2017.03.050 |
| Keywords | Hydroxynaphthalenecarboxamides; Hill reaction; Photosystem II; Structure-activity relationships |
| Description | N-(Alkoxyphenyl)-2-hydroxynaphthalene-1-carboxamides (series A) and N-(alkoxyphenyI)-1-hydroxy-naphthalene-2-carboxamides (series B) affecting photosystem (PS) II inhibited photosynthetic electron transport (PET) in spinach chloroplasts. Their inhibitory activity depended on the compound lipophilicity as well as on the position of the alkoxy substituent. The most potent PET inhibitors were 2-hydroxy-N-phenylnaphthalene-1-carboxamide and N-[3-(but-2-yloxy)phenyl]-2-hydroxynaphthalene-1-carboxamide within series A (IC50 = 28.9 and 42.5 mu M, respectively) and 1-hydroxy-N-(3-propoxyphenyl)naphthalene-2-carboxamide and 1-hydroxy-N-(3-ethoxyphenyl)-naphthalene-2-carboxamide (IC50= 2.0 and 3.1 mu M, respectively) within series B. The inhibitory activity of C'(3) or C'(4) alkoxy substituted compounds of series B was considerably higher than that of C'(2) ones within series A. The PET-inhibiting activities of both series were compared with the PET inhibition of isomeric N-alkoxypheny1-3-hydroxynaphthalene-2-carboxamides (series C) reported recently. Interactions of the studied compounds with chlorophyll a and aromatic amino acids present in pigment-protein complexes mainly in PS II were documented by fluorescence spectroscopy. The section between P(68)0 and plastoquinone Q(B) in the PET chain occurring on the acceptor side of PS II can be suggested as the site of action of the compounds. (C) 2017 Elsevier Ltd. All rights reserved. |