Antibacterial and Herbicidal Activity of Ring-Substituted 2-Hydroxynaphthalene-1-carboxanilides

Abstract

Abstract:In this study, a series of twenty-two ring-substituted 2-hydroxynaphthalene-1-carboxanilides were prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium marinum, M. kasasii, M. smegmatis. and M. avium paratuberculosis. The compounds were also tested for their activity related OPEN ACCESSMolecules 2013, 18 9398 to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. 2-Hydroxy-N-phenylnaphthalene-1-carboxanilide and 2-hydroxy-N-(3-trifluoromethylphenyl)naphthalene-1-carboxamide (IC 50 = 29 µmol/L) were the most active PET inhibitors. Some of tested compounds showed the antibacterial and antimycobacterial activity against the tested strains comparable or higher than the standards ampicillin or isoniazid. Thus, for example, 2-hydroxy-N-(3-nitrophenyl)naphthalene-1-carboxamide showed MIC = 26.0 µmol/L against methicillin-resistant S. aureus and MIC = 51.9 µmol/L against M. marinum, or 2-hydroxy-N-phenylnaphthalene-1-carboxamide demonstrated MIC = 15.2 µmol/L against M. kansasii. The structure-activity relationships for all compounds are discussed.

Preparation and Herbicidal Activity of Halogenated 8-Hydroxyquinoline-2-carboxanilides

“…Microwave-assisted synthesis [17,18,20] facilitated the process of obtaining ring-substituted 8-hydroxyquinoline-2-carboxanilides, thus synthesis of the target compounds was carried out only by one step. At first the carboxyl group was activated with phosphorus trichloride.…”

“…In addition, according to the results reported recently, some quinoline derivatives and their analogues/isosteres also showed noteworthy herbicidal activities [7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Although at present approximately 20 mechanisms of action of herbicides are known [21], 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 [22], and thereby inhibit photosynthesis [23][24][25].…”

“…Although at present approximately 20 mechanisms of action of herbicides are known [21], 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 [22], and thereby inhibit photosynthesis [23][24][25]. Some organic compounds, possessing an amide (-NHCO-) group, e.g., substituted anilides [11,[15][16][17][18]20], or a wide variety of compounds containing the quinoline system [9,10,[12][13][14]19] were found to interact with tyrosine radicals Tyr Z and Tyr D (or their surroundings) which are situated in D 1 and D 2 proteins on the donor side of PS II. Due to this interaction, interruption of the photosynthetic electron transport occurs.…”

“…Due to this interaction, interruption of the photosynthetic electron transport occurs. In the context of the previously-described azanaphtalenes and their isosteres [7][8][9][10][11][12][13][14][15][16][17][18][19][20], new simple modifications of quinoline that can possess interesting biological activity were investigated. The compounds were tested for their photosynthesis-inhibiting activity -the inhibition of photosynthetic electron transport in spinach chloroplasts (Spinacia oleracea L.).…”

Chromatographic and Computational Study of Hydro-lipophilic Properties of <em>N</em>-Alkoxyphenylhydroxy-naphthalenecarboxamides

“…Log k, calculated from the capacity factor k, is used as the lipophilicity index converted to log P scale [4]. N-Alkoxy-3-hydroxynaphthalene-2-carboxanilides, N-alkoxy-1-hydroxynaphthalene-2-carboxanilides and N-alkoxy-2-hydroxynaphthalene-1-carboxanilides were recently synthesized and tested for their antibacterial and antimycobacterial activity as well as for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts [9][10][11][12][13][14]. Since it was found that the lipophilicity of these significantly biologically effective agents determined their activity, in this study hydrolipophilic properties of all three series are investigated.…”