3651-62-5Relevant academic research and scientific papers
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.].
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 (2013/08/23)
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.
3,3-bis(aryl)-5-((N-(un)substituted)amido)naphthopyrans, their preparation, compositions and (co)polymer matrices containing them
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, (2008/06/13)
The object of the present invention is novel naphthopyran compounds as well as the compositions and (co)polymer matrices containing them. Said compounds have interesting photochromic properties. Another object of the present invention is a method of preparing said novel compounds.
SYNTHESIS AND PROPERTIES OF o-QUINONE DIAZIDES. PHOTOLYSIS OF 3-(p-TOLYLCARBAMOYL)-1,2-NAPHTHOQUINONE 1-DIAZIDE
Erlikh, R. D.,Zaitseva, L. G.,Sarkisyan, A. Ts.,Partalla, N. A.
, p. 1363 - 1367 (2007/10/02)
The photochemical decomposition of 3-(p-tolylcarbamoyl)-1,2-naphthoquinone 1-diazide in aqueous or alcohol solutions of dioxane or tetrahydrofuran leads to high yields of indenecarboxylic acid or its esters.Whereas indenecarboxylic acid exists exclusively in the form of the 3-isomer, the methyl and ethyl esters form a tautomeric mixtures (approximately 1:1.5) of the 1- and 3-isomers.The ratio of the isomeric esters does not depend significantly on temperature (20-50 deg C) or on the polarity and acid-base characteristics of the solvent.
