- Role of the Main and Auxiliary Ligands in the Nuclearity of Cu-Ln Complexes
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Trianionic ligands with an inner N2O2, an outer O2O2 or O2O coordination site and an oxygen atom coming from an amide function not involved in these sites yield dinuclear Cu-Ln complexes that self-ass
- Costes, Jean-Pierre,Rodriguez Douton, Maria-Jesus,Shova, Sergiu,Vendier, Laure
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- Mono- and binuclear complexes of iron(III) with 1,2-Bis(2-hydroxybenzamido)ethane
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Complexes of the type [(Fe(L))2O] · H2O (H2L=1,2-bis(2-hydroxybenzamido)ethane), [(Fe(L))2ter] · 5H2O H2ter=terephthalic acid), [Fe(L)bpy]BPh4 (bpy=2,2′-bipyridyl), and [Fe(L)phe
- Sme?kal, Zdene?k,S?indela?r?, Zdene?k,Klic?ka, Roman
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Read Online
- Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors
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Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV. Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties. The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used.
- Rivero-Buceta, Eva,Carrero, Paula,Doyagüez, Elisa G.,Madrona, Andrés,Quesada, Ernesto,Camarasa, María José,Peréz-Pérez, María Jesús,Leyssen, Pieter,Paeshuyse, Jan,Balzarini, Jan,Neyts, Johan,San-Félix, Ana
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p. 656 - 671
(2015/01/30)
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- Alkali-metal-ion-directed self-assembly of redox-active manganese(III) supramolecular boxes
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The ability to organize functional molecules into higher dimensional arrays with well-defined spatial relationships between the components is one of the major goals in supramolecular chemistry. We report here a new route for the preparation of supramolecu
- González-Riopedre, Gustavo,Bermejo, Manuel R.,Fernández-García, M. Isabel,González-Noya, Ana M.,Pedrido, Rosa,Rodríguez-Doutón, M. Jesús,Maneiro, Marcelino
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p. 2512 - 2521
(2015/03/30)
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- Bisamides as ligands in Suzuki coupling reactions catalyzed by palladium
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This protocol uses palladium chloride and bisamides as ligands for Suzuki cross-coupling reactions, in mild (25 for 2 h) aerobic conditions. This study was efficient for arylboronic acids and/or aryl bromides with activating or deactivating substituents in the ring with high yields (81-95%).
- Da Costa, Daniel P.,Nobre, Sabrina M.
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p. 4582 - 4584
(2013/08/23)
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- Highly selective binding of nitric oxide by CoIII and Fe III complexes
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In order to construct compounds with highly selective binding activity for NO, two CoIII and two FeIII complexes with square-planar N2O2-type donor sets, N-[2-(2-hydroxybenzylamino)ethyl]-2- hydroxybenzamide (H3L1) and 1,2-bis(2-hydroxybenzoylamino)ethane (H4L2), [CoIII(L1)] (1), Na[CoIII(L2)] (2), [FeIII(L1)] (3), and (PPh4)[FeIII(L2)] (4), were designed and synthesized. These compounds were characterized by electronic absorption, FT-IR, 1H-NMR spectroscopies, ESI-mass spectrometry, and elemental analyses. The redox potentials of the CoIII and Fe III complexes with L1, 1 and 3, have quasi-reversible waves at -0.51 and -0.49 V, respectively, and those with L2, 2 and 4, afforded reversible and irreversible waves at -0.96 and -1.04 V, respectively. Interestingly, all complexes quickly react with NO under an Ar atmosphere to form nitrosyl complexes, as monitored by UV-vis spectroscopy. The formation of nitrosyl complexes was confirmed by the appearance of the N-O stretching vibration at about 1650 cm-1; 1649 for 1, 1651 for 2, 1648 for 3, and 1650 cm -1 for 4. The reactivity of each of these complexes with other small molecules such as NO2-, NO3-, CO, and O2 was also studied. None of the complexes react with CO and O2. CoIII complexes 1 and 2 react with NO2 -, while FeIII complexes, 3 and 4, do not react with small amounts of NO2-. Complex 3 reacts with NO 2- at concentrations above 100 equiv. of NO 2-. We succeeded in preparing complexes with highly selective reactivity for NO. The Royal Society of Chemistry 2013.
- Zhang, Zizheng,Suwabe, Tatsuya,Ishikawa, Mai,Funahashi, Yasuhiro,Inomata, Tomohiko,Ozawa, Tomohiro,Masuda, Hideki
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p. 4470 - 4478
(2013/04/24)
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- A highly efficient copper-catalyzed method for the synthesis of 2-hydroxybenzamides in water
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An efficient copper-catalyzed synthetic method for the preparation of 2-hydroxybenzamides is described for the first time from 2-chlorobenzamide substrates using copper iodide/1,10-phenanthroline and a base, potassium hydroxide, in neat water. By using this reaction, a series of 2-hydroxybenzamides with functional groups such as fluoro, chloro, iodo, methoxy, amide, and alcohol have been obtained in 33-96% yield. Other aromatic 2-chloroarylamides such as naphthalene, pyridine, and thiophene are found to be equally compatible to the reaction. It is proposed that the reaction proceed via formation of copper-amide complex, which may facilitate the hydroxylation in water. Overall, the first report on copper-catalyzed hydroxylation reaction in water and first catalytic route for the synthesis of 2-hydroxybenzamides is presented. Simple purification procedure and convenience of employing low-cost reagents in neat water make this method practical and economical for the synthesis of 2-hydroxybenzamides. Georg Thieme Verlag Stuttgart · New York.
- Balkrishna, Shah Jaimin,Kumar, Sangit
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p. 1417 - 1426
(2012/06/30)
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- Synthesis and biological evaluation of some new 2-oxazoline and salicylic acid derivatives
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Starting from methyl salicylate and 2-amino-2-(hydroxymethyl)propane-1,3- diol 1a, or 2-amino- 2-methylpropane-1-ol 1b, the 2-oxazoline derivatives 2a, 2b or 3, as well as mono- 4a and 4b and bis- 5a and 5b derivatives of salicylic acid were synthesized. Reactions were performed by microwave irradiation in the presence of tetrabutylammonium bromide or metallic sodium as catalyst, as well as by conventional heating. Microwave-induced reaction of some diols, diamines and amino alcohols with methyl salicylate gave mono- and/or bis- derivatives of salicylic acid 4c, 5c, 5d, 6c, 8c, 7a, 7b, 8a and 8b. The mono- and bis-salicyloyl derivatives 4c, 5c and 5d were transformed to the corresponding phenyl-azo derivatives 9, 10c and 10d. The structure of compound 3 was proved by the X-ray analysis and the R-configuration on its stereocenter was confirmed. The antioxidant and cytotoxic activities of the synthesized derivatives were evaluated in a series of in vitro tests. Compounds 5d, 8b and 8c exhibited very strong activity against hydroxyl radical. Six 4c, 5d, 8a-c, 10c of 16 tested compounds inhibited growth of MDA-MB-231 cells at a nanomolar concentration. Compounds 8c and 10c showed high cytotoxicity against MCF7 cells, whereas compounds 4c, 5d, 8a-c and 10d showed high activity against K562 cells. ARKAT-USA, Inc.
- Djurendic, Evgenija,Vujaskovic, Sanja Dojcinovic,Sakac, Marija,Ajdukovic, Jovana,Gakovic, Andrea,Kojic, Vesna,Bogdanovic, Gordana,Klisuric, Olivera,Gasi, Katarina Penov
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experimental part
(2011/05/11)
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- Proximity effect on the general base catalysed hydrolysis of amide linkage: The role of cationic surfactant, CTABr
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The bis phenoxide forms of (1,2) bis(2-hydroxybenzamido) ethane(I) , (1,5) bis(2-hydroxybenzamido) 3-azapentane(II) , (1,3) bis(2-hydroxybenzamido) propane(III) , and (1,8) bis(2-hydroxybenzamido) 3,6- diazaoctane(IV) undergo facile hydrolysis of one of the amide groups (0.02 ≤ [OH?]T (mol dm? 3) ≤ 0.5, 10% MeOH (v/v) + H2O medium) without exhibiting [OH?] dependence. The reactivity trend follows I ~ II >> III ~ IV with low activation enthalpy {25.7±2.8 ≤ δH≠ (kJ mol?1) ≤ 64.8±7.0}. The high negative and comparable values of activation entropy{?234 ±8 ≤ δS≠ (J K?1 mol? 1) ≤ ?127 ± 20} are consistent with closely similar, and ordered transition states which can be assembled by favourably oriented phenoxide groups. The solvent kinetic isotope effect for I, κ H2O/κ D2O+H2O ~ 1 (20 and 50 volume% D2O) , indicates that proton transfer is not involved as a part of the rate controlling process. The observed slowing down of the rate of this reaction for I in the micellar pseudo phase of CTABr also supports the proposed mechanism. Under premicellar conditions, however, rate acceleration is observed, a consequence believed to be associated with the capping effect of the hydrophobic tail of the surfactant cation forming the reactive ion-pair, CTA+, (I-2H) 2? exclusively in the aqueous pseudo phase. Indian Academy of Sciences.
- Dash, Sarat C.,Dash, Anadi C.
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body text
p. 497 - 507
(2012/03/26)
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- Synthesis, antibacterial activities and molecular docking studies of peptide and Schiff bases as targeted antibiotics
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A series of peptide and Schiff bases (PSB) were synthesized by reacting salicylic acid, primary diamines with salicylaldehyde or its derivatives, and 40 of which were newly reported. The inhibitory activities against Escherichia coli β-ketoacyl-acyl carrier protein synthase III (ecKAS III) were investigated in vitro and molecular docking simulation also surveyed. Top 10 PSB compounds which posses both good inhibitory activity and well binding affinities were picked out, and their antibacterial activities against Gram-negative and Gram-positive bacterial strains were tested, expecting to exploit potent antibacterial agent with broad-spectrum antibiotics activity. The results demonstrate compound N-(3-(5-bromo-2-hydroxybenzylideneamino)propyl)-2-hydroxybenzamide (2d) can be as a potential antibiotics agent, displaying minimal inhibitory concentration values in the range of 0.39-3.13 μg/mL against various bacteria. Crown Copyright
- Cheng, Kui,Zheng, Qing-Zhong,Qian, Yong,Shi, Lei,Zhao, Jing,Zhu, Hai-Liang
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experimental part
p. 7861 - 7871
(2010/03/24)
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- Synthesis, characterisation and substitution reaction of trans-(diaqua) (N,N′-ethylene-bis-salicylamide)chromium(III) ion
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Trans-[Cr(Salm)(OH2)2]NO3 has been synthesized and characterized by various physicochemical methods. The kinetics of substitution of [Cr(Salm)(OH2)2]+ with different nucleophiles, viz., thi
- Dash,Brahma,Das,Das,Mohanty
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p. 2406 - 2411
(2007/10/03)
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- A convenient synthesis of nickel(II) and cobalt(II) complexes of unsymmetrical salen-type ligands and their application as catalysts for the oxidation of 2,6-dimethylphenol and 1,5-dihydroxynaphthalene by molecular oxygen
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Salen-type ligands 1-4 have been synthesized in high yields, from which the nickel(II) complexes 9-11 and the cobalt(II) complexes 12 and 13 have been prepared and characterized. The complexes have been assessed for their ability to activate molecular oxygen in the catalytic oxidation of phenols, namely, 2,6-dimethylphenol and 1,5-dihydroxynaphthalene. The nickel complexes 9-11 are inactive in the oxidation of the phenols but the cobalt complexes 12 and 13 show high catalytic activity.
- Adam, Waldemar,Saha-Moeller, Chantu R.,Ganeshpure, Pralhad A.
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- Interaction of N,N'-ethylene bis(salicylamide) with iron (III): A magneto-structural, electrochemical, and mechanistic investigation
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The reaction of N,N'-ethylene bis(salicylamide) (H2SALM) with ion(III) results in the formation of a 1: 1 complex in solution. The rate and activation parameters for the reactions, Fe(OH2)63+ + H2SALM
- Dash, Anadi C.,Mishra, Achyutananda
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p. 961 - 972
(2007/10/03)
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- A Convenient Method for Preparing Some New Macrocyclic Diamides
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A simple and convenient method for preparing macrocyclic diamides containing two sulfur atoms or two to four oxygen atoms of various ring sizes was developed.This two-step procedure is simply composed of reacting salicylic acid or 2-mercaptobenzoic acid w
- Liu, Lilian Kao,Hsieh, Tsing-Pai,Kuo, Sung-Ming
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p. 309 - 312
(2007/10/02)
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- Efficient synthesis of a range of benzo-substituted macrocyclic diamides
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Sixteen new 14-17-macrocyclic dibenzo and tribenzodioxadiamides and trioxadiamides (macrooxacyclams, e.g., 5,6,7,8,9,10,16,17-octahydrodibenzo[e,m][1,4,8,11]dioxadiazatetradecin e-5,10-dione) 13-28 have been prepared. Moderate to good yields (40-90%) of 1
- Ibrahim,Elwahy
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p. 503 - 508
(2007/10/02)
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- The Design of Multianionic Chelating Ligands for the Production of Inorganic Oxidizing Agents. Osmium Coordination Chemistry That Provides Stable Potent Oxidizing Agents and Stable Potent Reducing Agents
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The design of multianionic chelating ligands for use in producing new oxidizing agents is discussed.Two potentially tetradentate tetraanionic ligands, 1,2-bis(3,5-dichloro-2-hydroxybenzamido)ethane (H4CHBA-Et (1)) and 1,2-bis(3,5-dichloro-2-hydroxybenzami
- Anson, Fred C.,Christie, Judith A.,Collins, Terrence J.,Coots, Robert J.,Furutani, Tracy T.,et al.
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p. 4460 - 4472
(2007/10/02)
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