- Investigation of hydro-lipophilic properties of n-alkoxyphenylhydroxynaphthalenecarboxamides ?
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The evaluation of the lipophilic characteristics of biologically active agents is indispensable for the rational design of ADMET-tailored structure–activity models. N-Alkoxy-3-hydroxynaphthalene-2-carboxanilides, N-alkoxy-1-hydroxynaphthalene-2-carboxanilides, and N-alkoxy-2-hydroxynaphthalene-1-carboxanilides were recently reported as a series of compounds with antimycobacterial, antibacterial, and herbicidal activity. As it was found that the lipophilicity of these biologically active agents determines their activity, the hydro-lipophilic properties of all three series were investigated in this study. All 57 anilides were analyzed using the reversed-phase high-performance liquid chromatography method for the measurement of lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, a range of software lipophilicity predictors for the estimation of clogP values of a set of N-alkoxyphenylhydroxynaphthalenecarboxamides was employed and subsequently cross-compared with experimental parameters. Thus, the empirical values of lipophilicity (logk) and the distributive parameters (π) were compared with the corresponding in silico characteristics that were calculated using alternative methods for deducing the lipophilic features. To scrutinize (dis)similarities between the derivatives, a PCA procedure was applied to visualize the major differences in the performance of molecules with respect to their lipophilic profile, molecular weight, and violations of Lipinski’s Rule of Five.
- Kapustikova, Iva,Bak, Andrzej,Gonec, Tomas,Kos, Jiri,Kozik, Violetta,Jampilek, Josef
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- Enhanced Reactivity of Aerobic Diimide Olefin Hydrogenation with Arylboronic Compounds: An Efficient One-Pot Reduction/Oxidation Protocol
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A catalyst-free and efficient method for simultaneous olefin hydrogenation and oxidation of arylboronate esters to phenols with hydrazine hydrate and molecular oxygen is presented. The process is based on the utilization of a readily available Lewis acidic arylboron compound, which evades common problems associated with the catalyst-free aerobic hydrogenation of olefins with diimide. Using an operationally simple procedure, the protocol smoothly delivers phenol derivatives and various alkanes in excellent yields with remarkable functional group compatibility. The method allows the reaction to be scaled up to 1 g of the starting materials.
- Santra, Surojit,Guin, Joyram
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supporting information
p. 7253 - 7257
(2015/11/25)
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- Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides
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A series of fifteen new N-alkoxyphenylanilides of 3-hydroxynaphthalene-2-carboxylic acid was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra and M. avium subsp. paratuberculosis. Some of the tested compounds showed antibacterial and antimycobacterial activity against the tested strains comparable with or higher than that of the standards ampicillin or rifampicin. 3-Hydroxy-N-(2-propoxyphenyl)naphthalene-2-carboxamide and N-[2-(but-2-yloxy)-phenyl]-3-hydroxynaphthalene-2-carboxamide had MIC = 12 μM against all methicillin-resistant S. aureus strains; thus their activity is 4-fold higher than that of ampicillin. The second mentioned compound as well as 3-hydroxy-N-[3-(prop-2-yloxy)phenyl]-naphthalene-2-carboxamide had MICs = 23 μM and 24 μM against M. tuberculosis respectively. N-[2-(But-2-yloxy)phenyl]-3-hydroxynaphthalene-2-carboxamide demonstrated higher activity against M. avium subsp. paratuberculosis than rifampicin. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using THP-1 cells, and no significant lethal effect was observed for the most potent compounds. The compounds were additionally tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3-Ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 4.5 μM) was the most active PET inhibitor. The structure-activity relationships are discussed.
- Gonec, Tomas,Zadrazilova, Iveta,Nevin, Eoghan,Kauerova, Tereza,Pesko, Matus,Kos, Jiri,Oravec, Michal,Kollar, Peter,Coffey, Aidan,O'Mahony, Jim,Cizek, Alois,Kralova, Katarina,Jampilek, Josef
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p. 9767 - 9787
(2015/08/06)
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- COUMARIN DERIVATIVES AND METHODS OF USE IN TREATING CYSTIC FIBROSIS, CHRONIC OBSTRUCTIVE PULMONARY DISEASE, AND MISFOLDED PROTEIN DISORDERS
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Novel CFTR corrector compounds that are effective in rescuing halide efflux, delF508-CFTR protein processing, and apical functional chloride ion transport in a cell are provided. Also provided are methods for treating protein folding disorders (e.g., cyst
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Page/Page column 52; 53
(2014/10/04)
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- COUMARIN DERIVATIVES AND METHODS OF USE IN TREATING HYPERPROLIFERATIVE DISEASES
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Coumarin derivative compounds and methods for the treatment of hyperproliferative diseases, such as cancer, polycystic kidney disease, and fibrosis of different tissues (e.g., idiopathic pulmonary fibrosis), are provided. The methods include administering
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Page/Page column 51; 52
(2014/10/04)
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- An insight into the extraction of transition metal ions by picolinamides associated with intramolecular hydrogen bonding and rotational isomerization
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The clear connection between molecular structures of N-substituted picolinamides and extraction behaviour has been rationalized by highlighting the relationship between intramolecular hydrogen bonding and rotational isomerism. To this aim aromatic pyridine-2,6-dicarboxamides 1a-1c with N-substitution and their analogues 3a and 3b containing intramolecular hydrogen bonds were designed and synthesized. The results from the liquid-liquid extraction towards some representative transition metal picrates including Ag+, Hg 2+, Pb2+, Cd2+, Zn2+, Cu 2+, Co2+ and Ni2+ salts demonstrated that the higher selectivity and efficiency towards Hg2+ (88.6-95.4%) over other metal cations stem mainly from N-substitution via disruption of intramolecular H-bonding. X-ray structural analysis, and ordinary and variable-temperature proton and carbon NMR experiments provided supporting information for expounding the difference in extraction ability among these ligands, particularly the importance of N-substitution that leads to the formation of rotamers affecting the extraction process.
- Li, Yan,Jia, Yiming,Wang, Zhenwen,Li, Xianghui,Feng, Wen,Deng, Pengchi,Yuan, Lihua
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p. 29702 - 29714
(2014/08/05)
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- THIENOPYRIMIDINES FOR PHARMACEUTICAL COMPOSITIONS
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The present invention relates to novel pharmaceutical compositions of general formula (I) comprising thienopyrimidine compounds. Moreover, the present invention relates to the use of the thienopyrimidine compounds of the invention for the production of pharmaceutical compositions for the prophylaxis and/or treatment of diseases which can be influenced by the inhibition of the kinase activity of Mnk1 and/or Mnk2 (Mnk2a or Mnk2b) and/or variants thereof.
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Page/Page column 55
(2010/11/25)
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- Synthesis and characterization of some polyalkyl- and polyalkoxy-anilines
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Since poly-3-alkylthiophenes are more processible than polythiophene, it is expected that poly-o-alkyl and poly-o-alkoxyanilines will evince better processibility than polyaniline.Hence, poly-o-alkyl and poly-o-alkoxyanilines (alkyl=CH3, C2H5, C3H7, alkox
- Ahmad, Naseer,Feng, Ping,Schursky, Helen,Shah, Sharmila,Antonacci, Desiree,et al.
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p. 673 - 678
(2007/10/02)
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- GRAPHITE CATAlYZED REDUCTION OF AROMATIC AND ALIPHATIC NITRO COMPOUNDS WITH HYDRAZINE HYDRATE
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Aromatic and aliphatic nitro compounds were readily reduced to amino compounds in excellant yields with graphite and hydrazine hydrate.
- Han, Byung Hee,Shin, Dae Hyun,Cho, Sung Yun
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p. 6233 - 6234
(2007/10/02)
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- Herbicidal N-(haloacetyl)-N-(N'-methylenepyrrolidonyl)-2-alkoxyanilines useful as herbicides
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Herbicidal N-(haloacetyl)-N-(N'-methylenepyrrolidonyl)-2-alkoxyanilines are provided in this invention having the formula: STR1 where R is alkyl of 1-6 carbon atoms, R' is hydrogen or lower alkyl of 1-3 carbon atoms, and X is halogen. Another feature of the invention is the provision of N-(N'-methylenepyrrolidone)-2-alkoxyaniline or intermediates useful in making such herbicides. These intermediates are prepared by reaction of a 2-alkoxyaniline with an N-methylolpyrrolidone or an N-halomethylenepyrrolidone. The herbicide product than is obtained by acylation of the intermediate with a haloacetyl halide. The compounds of the present invention show good herbicidal activity against grassy weeds.
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