- Superior activity and selectivity of heterogenized cobalt catalysts for hydrogenation of nitroarenes
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The development of improved catalysts for highly selective hydrogenation of nitroarenes is described. For this purpose Co nanoparticles were supported on ordered mesoporous carbon CMK-3 and characterized in detail. The optimal CMK-3-CoPc catalyst exhibits excellent hydrogenation activity for several (hetero)aromatic nitro compounds and yielded the corresponding anilines under mild conditions (40 °C, 20 bar H2).
- Li, Wu,Artz, Jens,Broicher, Cornelia,Junge, Kathrin,Hartmann, Heinrich,Besmehn, Astrid,Palkovits, Regina,Beller, Matthias
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p. 157 - 162
(2019/01/10)
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- Determination of critical micellar concentration of homologous 2-alkoxyphenylcarbamoyloxyethyl-morpholinium chlorides
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The critical micellar concentrations of selected alkyloxy homologues of local anesthetic 4-(2-[(2-alkoxyphenyl)carbamoyl]oxy ethyl)morpholin-4-ium chloride with nc = 2, 4, 5, 6, 7, 8, and 9 carbons in alkyloxy tail were determined by absorption spectroscopy in the UV–vis spectral region with the use of a pyrene probe. Within the homologous series of the studied amphiphilic compounds, the ln(cmc) was observed to be dependent linearly on the number of carbon atoms nc in the hydrophobic tail: ln(cmc) = 0.705–0.966 nc. The Gibbs free energy, necessary for the transfer of the methylene group of the alkoxy chain from the water phase into the inner part of the micelle at the temperature of 25?C and pH ≈ 4.5–5.0, was found to be ?2.39 kJ/mol. The experimentally determined cmc values showed good correlations with the predicted values of the bulkiness of the alkoxy tail expressed as the molar volume of substituent R, as well as with the surface tension of the compounds.
- Stopková, Lenka,Inová, Jana Gali,Uchtová, Zuzana,Márik, Jozef ?i,Andriamainty, Fils
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- 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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- Co-based heterogeneous catalysts from well-defined Α-diimine complexes: Discussing the role of nitrogen
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Ar-BIANs and related α-diimine Co complexes were wet impregnated onto Vulcan XC 72 R carbon black powder and used as precursors for the synthesis of heterogeneous supported nanoscale catalysts by pyrolysis under argon at 800?°C. The catalytic materials feature a core-shell structure composed of metallic Co and Co oxides decorated with nitrogen-doped graphitic layers (NGr). These catalysts display high activity in the liquid phase hydrogenation of aromatic nitro compounds (110?°C, 50 bar H2) to give chemoselectively substituted aryl amines. The catalytic activity is closely related to the amount and type of nitrogen atoms in the final catalytic material, which suggests a heterolytic activation of dihydrogen.
- Formenti, Dario,Ferretti, Francesco,Topf, Christoph,Surkus, Annette-Enrica,Pohl, Marga-Martina,Radnik, J?rg,Schneider, Matthias,Junge, Kathrin,Beller, Matthias,Ragaini, Fabio
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- Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions
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A novel and efficient Fe-catalyzed direct C?H amination (NH2) of arenes is reported using a new redox-active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox-neutral conditions. This protocol has a broad substrate scope and could be used in the late-stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved in this transformation.
- Liu, Jianzhong,Wu, Kai,Shen, Tao,Liang, Yujie,Zou, Miancheng,Zhu, Yuchao,Li, Xinwei,Li, Xinyao,Jiao, Ning
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supporting information
p. 563 - 567
(2017/01/18)
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- Structure-based lead optimization and biological evaluation of BAX direct activators as novel potential anticancer agents
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The first direct activator of BAX, a pro-apoptotic member of the BCL-2 family, has been recently identified. Herein, a structure-based lead optimization turned out into a small series of analogues, where 8 is the most potent compound published so far. 8 was used as pharmacological tool to ascertain, for the first time, the anticancer potential of BAX direct activators and the obtained results would suggest that BAX direct activators are potential future anticancer drugs rather than venoms.
- Brancaccio, Diego,Cassese, Hilde,Coluccia, Antonio,Di Maro, Salvatore,Giustiniano, Mariateresa,Grassia, Gianluca,Ialenti, Armando,La Pietra, Valeria,La Regina, Giuseppe,Marinelli, Luciana,Martini, Claudia,Novellino, Ettore,Passacantilli, Sara,Silvestri, Romano,Stornaiuolo, Mariano,Taliani, Sabrina
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p. 2135 - 2148
(2015/03/30)
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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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- 2,2-Bis(ethoxycarbonyl)vinyl (BECV) as a versatile amine protecting group for selective functional-group transformations
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A 2,2-Bis(ethoxycarbonyl) vinyl- (BECV) group was used for the selective protection of amines at room temperature in the presence of potentially interfering functional groups such as OH, SH, COOH as well as other NH 2 groups. Several functional group transformations such as esterification, O-alkylation, O-acylation, N-alkylation, N-acylation, S-alkylation can selectively be carried out in the presence of the BECV group. The selective deprotection of the BECV group was achieved in a short time using ethylenediamine at room temperature while several other functional groups such as benzoate, aliphatic esters, amides and ethers remain intact. The BECV group shows orthogonal stability against the common protecting groups such as Fmoc, Cbz and Boc.
- Ilangovan, Andivelu,Kumar, Rajendran Ganesh
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supporting information; experimental part
p. 2938 - 2943
(2010/07/02)
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- Iodine-mediated cyclisation of thiobenzamides to produce benzothiazoles and benzoxazoles
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Synthesis of benzothiazoles by reaction of iodine with thiobenzamides, which do not possess an ortho alkoxy or ester group, is described. The unlikely synthesis of benzoxazoles from reaction of 2-alkoxythiobenzamides with iodine is also reported.
- Downer-Riley, Nadale K.,Jackson, Yvette A.
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p. 10276 - 10281
(2008/02/13)
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- Amination of arenes with N,N-dimethyl-2-imidazolidinone O-methoxyacetyloxime
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Treatment of nucleophilic arenes with N,N-dimethyl-2imidazolidinone O-methoxyacetyloxime and SnCl4 produced the corresponding N-arylimines, which were converted to anilines by hydrolysis with CsOH and to N-methylanilines by LiAlH4 reduction.
- Baldovini, Nicolas,Kitamura, Mitsuru,Narasaka, Koichi
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p. 548 - 549
(2007/10/03)
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- The novel reduction systems: NaBH4-SbCl3 or NaBH4-BiCl3 for conversion of nitroarenes to primary amines
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Nitroarenes can be conveniently reduced to primary amines in good to excellent yields by sodium borohydride in the presence of bismuth chloride or antimony chloride.
- Ren,Pan,Dong,Wu
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p. 3799 - 3803
(2007/10/03)
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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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- Photolysis of Benztriazole in Alcoholic Glass at 77 K
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The photolysis of benztriazole (1) in alcoholic glass at 254 nm has been studied by UV absorption, emission, IR, and mass spectroscopies.Bond scission of the N-NH bond of 1 originates from the S1(?,?*) state to give the azo compound 2, having an absorption band at 423 nm and an IR absorption band at 2070 cm-1.This yellow azo intermediate is decomposed thermally or photochemically.Iminocyclohexadienylidene (3) with resonance structures of a carbene (3a) and a biradical (3b) may be produced as a colorless second intermediate.On the basis of reaction product analysis from the rigid-phase photolysis of 1 at 77 K compared to those in liquid solution and gas-phase photolyses, the reaction paths of 3 to yield aniline, o-anisidine, o-ethoxyaniline, and 1-cyanocyclopentadiene are discussed in terms of the spin states of 3.
- Shizuka, Haruo,Hiratsuka, Hiroshi,Jinguji, Mamoru,Hiraoka, Hiroyuki
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p. 1793 - 1797
(2007/10/02)
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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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- Azo reactive dyestuffs having an aryl-triazinyl-aryl diazo component
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Optionally metallized azo dyestuffs which in the form of the free acid correspond to the formula STR1 wherein K is the radical of a benzene, naphthalene, pyrazolone, pyridone, pyrimidone, acetoacetic acid arylide or aminopyrazole coupling component; A is a non-ionic substituent; X is STR2 wherein W is a direct bond or a bridge member to a C atom of the benzene or naphthalene nucleus or the coupling component K; R is hydrogen or C1 -C4 -alkyl; B is a direct bond or a bridge member, especially -CO- or -SO2 -, to a C atom of Q; Q is a reactive radical; m is 0, 1 or 2; n is 0, 1 or 2; p is 0 or 1; q is 0, 1 or 2; and r is 0 or 1; and their use for the dyeing and printing of natural and regenerated cellulose fibre materials such as cotton and rayon, as well as natural and synthetic polyamide fibre materials, for example those of wool, silk, poly-ε-caprolactam or polycondensate of hexamethylene-diamine and adipic acid. The dyeings obtained, espeically those on cotton and rayon, are distinguished by good fastness properties, especially fastness to wet processing and to light.
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- NOVEL TRANSETHERIFICATION IN CATALYTIC REDUCTION OF 4-ALKOXYNITROBENZENES IN ALCOHOL-SULFURIC ACID SOLUTION
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In catalytic reduction (5percent Pt-C, 1 atm H2) of 4-alkoxynitrobenzenes (R1O-C6H4-NO2) in alcohol(R2OH)-sulfuric acid solution at room temperature, the reduction was found to be accompanied by transetherification to afford R2O-C6H4-NH2.
- Sone, Takaaki,Teraoka, Tadayoshi,Katada, Sho-ji,Ohkubo, Makoto,Karikura, Masami,et al.
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p. 1259 - 1262
(2007/10/02)
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