135-61-5Relevant articles and documents
Antibacterial and herbicidal activity of ring-substituted 3-hydroxynaphthalene-2-carboxanilides
Kos, Jiri,Zadrazilova, Iveta,Pesko, Matus,Keltosova, Stanislava,Tengler, Jan,Gonec, Tomas,Bobal, Pavel,Kauerova, Tereza,Oravec, Michal,Kollar, Peter,Cizek, Alois,Kralova, Katarina,Jampilek, Josef
, p. 7977 - 7997 (2013)
In this study, a series of twenty-two ring-substituted 3-hydroxy- Nphenylnaphthalene- 2-carboxanilides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four Staphylococcus strains and against two mycobacterial species. 3-Hydroxy-N-(2-methoxyphenyl)naphthalene-2-carboxamide showed high biological activity (MIC = 55.0 μmol/L) against S. aureus as well as methicillinresistant strains. N-(2-Fluorophenyl)-3-hydroxynaphthalene-2- carboxamide showed higher activity (MIC = 28.4 μmol/L) against M. marinum than the standard isoniazid and 3-hydroxy-N-(4-nitrophenyl)naphthalene-2- carboxamide expressed higher activity (MIC = 13.0 μmol/L) against M. kansasii than the standard isoniazid. Cytotoxicity assay of effective antimicrobial compounds was performed using the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC50 value of the most active compound 3-hydroxy-N-(3-nitrophenyl)naphthalene-2-carboxamide was 16.9 μmol/L. The structure-activity relationships of all compounds are discussed.
3-Hydroxynaphthalene-2-carboxanilides and their antitrypanosomal activity
Kos, Jiri,Kapustikova, Iva,Clements, Carol,Gray, Alexander I.,Jampilek, Josef
, p. 887 - 892 (2018/02/12)
Abstract: Series of ring-substituted 3-hydroxynaphthalene-2-carboxanilides were screened for their in vitro activity against wild-type S427 (bloodstream form) of Trypanosoma brucei brucei. 3-Hydroxy-N-(3-trifluoromethylphenyl)- and 3-hydroxy-N-(4-trifluoromethylphenyl)naphthalene-2-carboxamides showed the highest biological activity (MIC?=?1.56 and 2.08?μmol/dm3, respectively). Antitrypanosomal activity was correlated with the experimentally determined lipophilicity and acid–base dissociation constants of the compounds as well as with the calculated electronic properties of individual anilide substituents expressed as Hammett’s σ parameters. The substitution in the meta- or para-position of anilide of derivatives with higher lipophilicity by an electron-withdrawing moiety is favourable for higher activity. The optimum thermodynamic pKa T value was found to be ca. 7.5. The structure–activity relationships of all compounds are discussed. Graphical abstract: [Figure not available: see fulltext.].
Process for the preparation of pure, aromatic o-hydroxy-carboxylic acid aryl amides
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, (2008/06/13)
Process for the preparation of pure aromatic o-hydroxy-carboxylic acid aryl amides by condensing an aromatic o-hydroxy-carboxylic acid with an aryl amine in the presence of phosphorus chlorides in an organic solvent or diluent, which process comprises treating the reaction mixture or the reaction product with 1 to 25 %, calculated on the weight of the reaction product, of an aliphatic amino-polycarboxylic acid as chelate forming agent. It is not necessary to purify the products, because they are obtained in such a pure form that they can be used directly as coupling components for azo pigments.