- 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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- Synthesis method of m-phenetidine by one-pot reaction
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The invention discloses a synthesis method of m-phenetidine by a one-pot reaction. The method comprises the following steps: m-aminophenol, alkali and a solvent are thrown into a reaction vessel, and then only an alkylating agent or a catalyst and an alkylating agent are added at the same time, after materials are added, the reaction vessel is enclosed, and stirring is carried out for 0.5-1 hour at room temperature; the temperature is raised to 40-80 DEG C, a reaction is carried out for 1-8 hours, after the reaction, obtained reaction solution is cooled to room temperature and filtered, and filtrate is obtained; reduced pressure distillation for the filtrate is carried out, and m-phenetidine is obtained. The synthesis method of m-phenetidine has the characteristics of low reaction temperature, high safety performance, convenient operation, high purity and high yield of the product, etc.
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Paragraph 0033; 0034
(2016/12/07)
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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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- [Cp?RhCl2]2-catalyzed alkyne hydroamination to 1,2-dihydroquinolines
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[Cp?RhCl2]2 catalyzes the formation of 1,2-dihydroquinolines from the reaction of two terminal alkynes and an aniline. This reaction is believed to proceed via an alkyne hydroamination followed by an alkyne insertion.
- Kumaran, Elumalai,Leong, Weng Kee
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p. 1779 - 1782
(2015/05/20)
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- Design, synthesis, and anticonvulsant activity evaluation of 4-(3-Alkoxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-ones
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A series of 4-(3-alkoxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-ones were synthesized using the appropriate synthetic route and evaluated experimentally in the maximal electroshock test; their neurotoxicities were evaluated by the rotarod neurotoxicity test. The structures of these compounds were confirmed by IR, MS, 1H-NMR, and elementary analysis. All target compounds exhibited anticonvulsant activity to varying degrees in the maximal electroshock test. 4-(3-Benzyloxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one (4i) was the most promising compound with an ED50 value of 30.5 mg/kg and a protective index (PI) of 18.63, showing a higher safety than the standard carbamazepine (PI = 6.45). In addition, the potency of compound 4i against seizures induced by pentylenetetrazole and 3-mercaptopropionic acid suggested its broad-spectrum activity, and the mechanisms of action including inhibition of voltage-gated ion channels and modulation of GABAergic activity might be involved in its anticonvulsant activity. Copyright
- Shu, Bing,Zheng, Yan,Wang, Shi-Ben,Deng, Xian-Qing,Quan, Zhe-Shan
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p. 127 - 133
(2013/04/10)
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- Hydrogenative cleavage of azo compounds catalyzed by commercial zinc dust using ammonium acetate
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Addition of ammonium acetate followed by commercial zinc dust to the solution of azo compounds in methanol appears to offer a general and convenient means for reducing both symmetrical and unsymmetrical azo compounds to the corresponding amine/s at ambient temperature. Many other reducible and hydrogenolysable groups like -OCH3, -OH, -COOH, -CH3, -COCH3 and halogens are tolerated. The reduction is fast, clean, high yielding and inexpensive compared to earlier methods.
- Srinivasa,Abiraj,Gowda, D. Channe
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p. 192 - 195
(2007/10/03)
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- Facile Transfer Hydrogenation of Azo Compounds to Hydrazo Compounds and Anilines by Using Raney Nickel and Hydrazinium Monoformate
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Azo compounds are conveniently reduced to either partially reduced hydrazo compounds or completely reduced anilines by employing Raney nickel in presence of hydrazinium monoformate depending upon reaction conditions. The other reducible moieties like -COOH and halogens are tolerated. The reduction process is selective, rapid and high yielding.
- Prasad,Gowda, Shankare,Gowda, D. Channe
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- Rapid cleavage of azo compounds to amine/s using Raney nickel and ammonium formate or formic acid
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Azo compounds, both symmetrical and unsymmetrical are cleaved to amine/s by using Raney nickel and ammonium formate or formic acid in methanol at room temperature. The reductive cleavage is very fast, clean, cost effective and high yielding as compared to earlier methods and many other functionality such as -OH, -CH3 -OCH3, -COOH, -COCH3 and halogen remained unaffected.
- Gowda, D. Channe,Gowda, Shankare,Abiraj
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p. 1774 - 1776
(2007/10/03)
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- KINETICS OF ALKALINE HYDROLYSIS AND CORRELETION STUDIES OF m- AND p-SUBSTITUTED PIPERIDINOETHYL PHENYLCARBAMATES
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Kinetics of alkaline hydrolysis have been studied with a series of 15 m- and p-substituted piperidinoethyl phenylcarbamates.The rate constants have been determined at 70, 60, 50, and 40 deg C and the activation parameters have been calculated.These values have been correlated with the substituent constants ?, , , F, R, ?.Validity of the Hammett equation and the Swain-Lupton equation has been confirmed in the series studied and for the p-derivatives, respectively.The lipophilicity parameter ? does not correlate with the values found.
- Stankovicova, Maria,Cizmarik, Jozef
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p. 1846 - 1853
(2007/10/02)
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- Fiber-reactive disazo brown dye having vinylsulfone-type reactive group
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A compound, or a salt thereof, represented by the following formula, STR1 wherein A is a substituted or unsubstituted phenylene or naphthylene group, B is STR2 in which R3 is a hydrogen atom or a lower alkyl, lower alkoxy, acylamino or ureido group, and R4 is a hydrogen atom or a lower alkyl or lower alkoxy group, R1 and R3 are independently a hydrogen atom or a substituted or unsubstituted lower alkyl group, X is a substituted or unsubstituted amino, lower alkoxy, substituted phenoxy or sulfo group, Y is --SO2 CH=CH2 or --SO2 CH2 CH2 Z, in which Z is a group capable of being split by the action of an alkali, and m is 2 or 3, which is useful for dyeing hydroxyl group- or amide group-containing fiber materials to give dyed products of a brown color having excellent fastness properties with good build-up property.
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- In vitro deacetylation studies of acetamidophenolic compounds in rat brain, liver and kidney
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The in vitro deacetylation of ortho-, meta- and para-substituted acetophenetidines and acetamidophenols including acetanilide by arylacylamidases in rat brain, liver and kidney was investigated. In general, deacetylation rates were highest in liver and kidney preparations, whereas brain exhibited lower enzyme activities. Acetophenetidines were more suitable N-deacetylation substrates in comparison to acetamidophenols, whereby o-substituted compounds were split more easily than their corresponding m- or p-analogues. Among the arylacylamides tested, o-acetophenetidine was the predominant substrate in all tissues. It was deacetylated far more rapidly than phenacetin. The enzymic deacetylation of acetophenetidines in kidney and brain was inhibited by p-nitrophenylacetate revealing that N-acetylamides as well as O-acetyl esters undergo similar degradation by carboxylesterase-amidases. The organophosphorous diester bis(p-nitrophenyl)-phosphate which is known to be a rather selective inhibitor of acetanilide-cleaving hydrolases in rat liver suppressed the deacetylation of acetanilide in all tissues investigated. In contrast to acetanilide, the deacetylation of acetophenetidines was inhibited by bis(p-nitrophenyl)-phosphate in liver and kidney, but bis(p-nitrophenyl)-phosphate was far less active against acetophenetidine hydrolases in brain.
- Baumann,Von Bruchhausen,Wurm
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p. 1278 - 1282
(2007/10/02)
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- Effect of Meta and Para Substituents on the Stannous Chloride Reduction of Nitrobenzenes in Aqueous Ethanol
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The rate of reduction of 24 meta- and para-substituted nitrobenzenes with SnCl2 catalyzed by HCl in ethanol-water (90 : 10 v/v) at 30 degC has been measured iodometrically.The rate is expressed as υ = kst0.5, suggesting that the sole active reducing species is SnCl3- and the dissociation of HCl is very small.The effect of meta and para substituents in which the solvation of the substituent is taken into account was examined with the Hammett equation, which gave a ρ value of 2.1 +/- 0.1.Yukawa-Tsuno and Taft equations, in which resonance and inductive effects are separated, are also discussed.
- Xing, Wen-Kang,Ogata, Yoshiro
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p. 2515 - 2520
(2007/10/02)
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- KINETICS AND MECHANISM OF HYDROGENATION OF NITROBENZENE BY SYSTEM
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The initial rate of nitrobenzene hydrogenation catalyzed homogenously by cobaloximes is second order in cobalt and is inhibited by an excess of nitrobenzene.It also strongly depends upon cobaloxime:amino ratio.These observations were rationalized in terms of binuclear nitrobenzene-complexed intermediate as crucial in the catalytic cycle.This assumption was further supported by the unusual selectivity of cobaloxime systems, which does not catalyze hydrogenation of ortho-substituted nitrobenzenes.
- Tyrlik, Stanislaw,Kwiecinski, Michal,Kawczynski, Lech
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p. 1947 - 1957
(2007/10/02)
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