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1.
Bottari B Maccari R Monforte F Ottanà R Vigorita MG Bruno G Nicolò F Rotondo A Rotondo E 《Bioorganic & medicinal chemistry》2001,9(8):2203-2211
The reaction of 2,6-diacetylpyridine (dap) and isonicotinoyl- or benzoylhydrazide leads to bishydrazones H(2)dapin (1a) and H(2)dapb (1b), respectively. The condensation can either take place as a bimolecular kinetic process between the two reactants or as a monomolecular metal-templated synthesis in the presence of nickel(II) ions. In the latter case the reaction products are charged 2,6-diacetylpyridine bis(hydrazone) nickel(II) complexes, which can be easily deprotonated to neutral hydrazonates. Diffractometric analysis of one of these [Ni(dapb)](2) (8b) has shown a binuclear structure with two octahedral nickel(II) ions bridged by two helicoidal dap (bishydrazonates) in a spheroidal structure of C(2V) symmetry. The synthesized complexes 8 are promising as antimycobacterial agents against M. tuberculosis H37Rv. In particular, 8b displays significant activity (MIC=0.025 microg/mL) 10-fold higher than rifampin and equal to isoniazid, while its ligand is ineffective. Compound 8b is also capable of reducing HIV-induced cytopathogenic effect in human T(4 )lymphocytes. 相似文献
2.
Nuria A. Illn-Cabeza Sonia B. Jimnez-Pulido Jos M. Martínez-Martos María J. Ramírez-Expsito Miguel N. Moreno-Carretero 《Journal of inorganic biochemistry》2009,103(8):1176-1184
Three new Cd(II) complexes with the Schiff base ligand derived from the condensation 1 + 2 of 2,6-diacetylpyridine and 5,6-diamino-1,3-dimethyluracil have been “in template” synthesized. The molecular structures of complexes were determined by single-crystal X-ray diffraction. The metal center shows a very distorted mer-bis-tridentate CdN6 octahedral geometry as consequence of the reduced bite angles of the ligand and the existence of long-distanced interactions with donor atoms in the neighbourhood. The luminescent properties of complexes in CH3CN solution were investigated showing the emission energies depend on the uracil part of the ligand. The evaluation of their biological properties against C6 glioma cell line indicates that cadmium(II) complexes could be an interesting tools to treat drug-resistant brain tumors. 相似文献
3.
Ilia Levitin Marina Tsikalova Natalia Sazikova Vladimir Bakhmutov Zoya Starikova Aleksandr Yanovsky Yuri Struchkov 《Inorganica chimica acta》1998,270(1-2):169-176
Organocobalt(III) complexes with Schiff bases derived from a β-diketone bearing both an alkyl and an aryl group have been prepared. The template syntheses using benzoylacetone and ethylenediamine as complexing agents provide a route to alkylcobalt chelates with the corresponding tri- and tetradentate Schiff bases. However, if a β-diketone with two aryl groups, e.g. dibenzoylmethane, was employed as the starting ketoenol component, no organometallic products were detected; a new mixed-ligand ‘inorganic’ chelate of cobalt(II), [Co{O=C(Ph)CH=C(Ph)O}2(en)], was isolated instead. Its structure as well as that of one of the alkylcobalt complexes with a tridentate Schiff base composed of benzoylacetone and ethylenediamine have been established by X-ray techniques. The current scope of the template synthesis of alkylcobalt complexes with Schiff bases is summarized. 相似文献
4.
New lanthanide complexes of salicylaldehyde- Schiff bases with salicyloyl hydrazide and anthranilic acid, were synthesized by a novel method consisting of refluxing the mixtures of Schiff base ligands and lanthanide trichloroacetate in acetone. Solid complexes of formulae Ln(SHSASB)3·2H2O and Ln2(AASASB)3·2H2O where Ln = La---Yb and Y, were isolated. Pronto NMR and IR spectra for the complexes reveal the bidentate binding of both the Schiff base ligands to the lanthanide ion. Electronic spectra along with the conductance data for the complexes indicate a coordination number of six for the lanthanide ion in the complexes of both the Schiff bases. 相似文献
5.
Hueso-Ureña F Illán-Cabeza NA Moreno-Carretero MN Martínez-Martos JM Ramírez-Expósito MJ 《Journal of inorganic biochemistry》2003,94(4):326-334
The synthesis, spectroscopic (IR, 1H and 13C NMR, UV-Vis-NIR, EPR), magnetic measurements and biological studies of a number of complexes of Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Au(III) and Hg(II) of the Schiff base derived from the 1:2 condensation of 2,6-diformyl-4-methylphenol and 5-aminouracil, ((5-[[(3-[[(2,4-dioxopyrimidin-5(1H,3H)-yl)imino]methyl]-2-hydroxy-5-methylphenyl)methylene]amino]pyrimidine-2,4(1H,3H)-dione, hereafter denoted as BDF5AU) are reported. In all cases, the complexes appear to be monomeric. The deprotonated ligand in the phenolic oxygen atom shows a tridentate coordination mode through the two azomethine nitrogen atoms and the phenolic oxygen atom. The coordination of the neutral ligand takes place through the phenolic oxygen atom and one azomethine nitrogen atom and the carbonylic oxygen atom in fourth position of one uracil ring. The biological properties of some perchlorate complexes on the activity of some neutral, acid, basic and omega aminopeptidases (AP) are assayed, demonstrating a general inhibitory effect. Neutral and basic AP are mainly inhibited by Cu(II), Ni(II) and Cd(II) complexes, although tyrosyl-AP is activated by Zn(II) complex. Glutamyl-AP but not aspartyl-AP is inhibited by all the complexes assayed excepting Zn(II) complex. Finally, omega AP is inhibited by Ni(II) and Cd(II) complexes. 相似文献
6.
Synthesis and luminescence properties of polymer–rare earth complexes containing salicylaldehyde‐type bidentate Schiff base ligand
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Using molecular design and polymer reactions, two types of bidentate Schiff base ligands, salicylaldehyde–aniline (SAN) and salicylaldehyde–cyclohexylamine (SCA), were synchronously synthesized and bonded onto the side chain of polysulfone (PSF), giving two bidentate Schiff base ligand‐functionalized PSFs, PSF–SAN and PSF–SCA, referred to as macromolecular ligands. Following coordination reactions between the macromolecular ligands and Eu(III) and Tb(III) ions (the reaction occurred between the bonded ligands SAN or SCA and the lanthanide ion), two series of luminescent polymer–rare earth complexes, PSF–SAN–Eu(III) and PSF–SCA–Tb(III), were obtained. The two macromolecular ligands were fully characterized by Fourier transform infrared (FTIR), 1H NMR and UV absorption spectroscopy, and the prepared complexes were also characterized by FTIR, UV absorption spectroscopy and thermo‐gravity analysis. On this basis, the photoluminescence properties of these complexes and the relationships between their structure and luminescence were investigated in depth. The results show that the bonded bidentate Schiff base ligands, SAN and SCA, can effectively sensitize the fluorescence emission of Eu(III) and Tb(III) ions, respectively. PSF–SAN–Eu(III) series complexes, namely the binary complex PSF–(SAN)3–Eu(III) and the ternary complex PSF–(SAN)3–Eu(III)–(Phen)1 (Phen is the small‐molecule ligand 1,10‐phenanthroline), produce strong red luminescence, suggesting that the triplet state energy level of SAN is lower and well matched with the resonant energy level of the Eu(III) ion. By contrast, PSF–SAN–Eu(III) series complexes, namely the binary complex PSF–(SCA)3–Tb(III) and the ternary complex PSF–(SCA)3–Tb(III)–(Phen)1, display strong green luminescence, suggesting that the triplet state energy level of SCA is higher and is well matched with the resonant energy level of Tb(III). 相似文献
7.
S. Tamburini P.A. Vigato M. Gatos L. Bertolo U. Casellato 《Inorganica chimica acta》2006,359(1):183-196
The mononuclear macrocyclic lanthanide(III) complexes, [Ln(H2L)(H2O)4]Cl3 (Ln = Y, La, Ce, Cu, Tb, Yb, Lu; H2L = H2LA, H2LB, H2LC) were prepared by condensation 3,3′-(3,6-dioxaoctane-1,8-diyldioxy)bis(2-hydroxybenzaldehyde) or 3,3′-(3-oxapentane-1,5-diyldioxy)bis(2-hydroxybenzaldehyde) with 1,5-diamino-3-azamethylpentane or 1,7-diamino-3-azamethylheptane in the presence of LnCl3 · nH2O as templating agent. The asymmetric [1+1] ligands H2LA, H2LB and H2LC contain one smaller or larger N3O2 Schiff base site and one crown-ether like O2O4 or O2O3 site. The preference of the lanthanide ion to reside into the Schiff base or the crown-ether like chamber was investigated in the solid state and in methanol or dimethylsulfoxide solution. It was found that in the solid state or in methanol the lanthanide(III) ion coordinates into the O2On site while in dimethylsulfoxide demetalation and partial metal ion migration from the O2On into the N3O2 chamber occur. The mononuclear lanthanide(III) complexes [Ln(H2L)(H2O)4]Cl3 with the Ln3+ ion in the O2On site have been used as ligands in the synthesis of the heterodinuclear complexes LnLn′(L)(Cl)4 · 4H2O by reaction with the appropriate Ln′(III) chloride in methanol and in the presence of base. The related homodinuclear complexes Ln2(L)(Cl)4 · 4H2O have been prepared by the one-pot condensation of the appropriate precursors in the presence of base and of the lanthanide(III) ion as templating agent.The single-crystal X-ray structure of [Eu(H2LA)(H2O)4]Cl3 · 5H2O has been determined. The europium ion is nine-coordinated in the O2O3 ligand site and bonded to four water molecules and the coordination polyhedron can be described as a square monocapped antiprism.The site occupancy of the different lanthanide(III) ions and the physico-chemical properties arising from the different dinuclear aggregation and/or from the variation of the crown-ether shape have been investigated by IR and NMR spectroscopy, MS spectrometry and SEM-EDS microscopy. In particular, site migration and/or transmetalation reactions, together with demetalation reactions, have been monitored by NMR studies in methanol and dimethylsulfoxide. It was found that these processes strongly depend on the shape of the two coordination chambers, the solvent used and the radius of the lanthanide(III) ions. Thus, these molecular movements can be tuned by changing appropriately these parameters. 相似文献
8.
《Inorganica chimica acta》1986,116(2):163-169
Optically active Schiff base ligands have been formed by the condensation of various salicylaldehydes with a series of chiral amino alcohols. The Eu(III) derivatives of these ligands were obtained as oligomeric materials, exhibiting an empirical 1:1 metal:ligand stoichiometry. The complexes were found to be somewhat soluble in chloroform, where they existed primarily as trimeric species. The optical activity experienced by the Eu(III) ion was observed to be dominated by the presence of configurational effects, corresponding to a dissymmetric arrangement of Schiff base ligands about the Eu(III) ion. 相似文献
9.
10.
Arunashree Panda Author Vitae Snigdha Panda Author Vitae Author Vitae Harkesh B. Singh Author Vitae 《Inorganica chimica acta》2011,372(1):17-31
This paper highlights our work to establish a new class of macrocycles based on Schiff base condensation chemistry. The chemistry of a series of azomethine macrocycles, with selenium/tellurium atoms in o-positions with respect to the CN bond is discussed. These are the first Schiff base macrocycles to incorporate selenium or tellurium atom in the ring. The strong stabilization of the 10-E-3 (E = Se/Te) structures of these macrocycles by E-N coordination permits the access to these novel macrocycles by [2+2] template-free condensation of bis(aldehyde) with primary diamines. The success of cyclization has been confirmed by the usual methods of IR, NMR and X-ray structural determinations. After a brief discussion of the synthetic methods adopted for these macrocycles, their complexing abilities toward different metal ions are covered. The macrocyclic polyamine ligands, derived by reduction of the corresponding Schiff bases, readily form complexes with a range of metal ions. This allows a comparison of the properties of complexes of these ligands with those derived from the Schiff bases containing the same denticity but having a different flexibility. The selena- and tellura-macrocycles reported by other groups in the field are also included for comparison. Also discussed is the anion binding studies of some of these macrocycles. 相似文献
11.
Mohammad Akbar Ali Aminul Huq Mirza Ray J. Butcher M. T. H. Tarafder Manaf A. Ali 《Inorganica chimica acta》2001,320(1-2):1-6
The Schiff base formed by condensation of 2,6-diacetylpyridine with S-benzyldithiocarbazate (H2SNNNS) behaves as a pentadentate ligand, forming a nickel(II) complex of empirical formula Ni(SNNNS)·H2O that is high-spin with a room-temperature magnetic moment of 2.93 B.M. Spectroscopic data indicate that the ligand coordinates with the nickel(II) ion via the pyridine nitrogen atom, the azomethine nitrogen atom and the thiolate sulfur atom. The crystal and molecular structure of the nickel(II) complex was determined by X-ray crystallography. The complex crystallizes in the monoclinic system, space group C2/c, with a=15.849(2), b=18.830(2) and c=18.447(2) Å and =90°, β=102.179(6)°, γ=90° and Z=8. The crystal structure analysis shows that the complex is dinuclear, [Ni(SNNNS)]2·2H2O, in which the nickel(II) ions are bridged by the two pyridine nitrogen atoms of two fully deprotonated ligands. The NiN4S2 coordination geometry about each nickel(II) ion can be described as a distorted octahedron. The Schiff base and its nickel(II) complex were tested against four pathogenic bacteria (Bacillus subtilis, Pseudomonas aeruginosa, methicillin-resistant Staphylococcus and B. subtilis (wild type B29) and pathogenic fungi (Saccharomyces ceciricae, Candida albicans, Candida lypolitica and Aspergillus ochraceous) to assess their antimicrobial properties. Both compounds exhibit mild antibacterial and antifungal activities against these organisms. The anticancer properties of these compounds were also evaluated against Human T-lymphoblastic leukaemia cell lines. The Schiff base exhibits marked cytotoxicity against these cells, but its nickel(II) complex is inactive. 相似文献
12.
Benzoylhydrazones and semicarbazones derived from 2,6-diacetylpyridine react with common dioxouranium(VI) compounds such as uranyl nitrate or [NBu4]2[UO2Cl4] to form air-stable complexes. 2,6-Diacetylpyridinebis(benzoylhydrazone) (H2L1), 2,6-diacetylpyridinebis(N4-phenylsemicarbazone) (H2L2) and the asymmetric proligand 2,6-diacetylpyridine(benzoylhydrazone)(N4-phenylsemicarbazone) (H2L3) give yellow products of the composition [UO2(L)]. The neutral compounds contain doubly deprotonated ligands and possess uranium atoms with distorted pentagonal-bipyramidal coordination spheres. The equatorial coordination spheres of the metal atoms can be extended by the addition of a monodentate ligand such as pyridine or DMSO. The uranium atoms in the resulting complexes have hexagonal-bipyramidal coordination environments with the oxo ligands in axial positions.X-ray diffraction studies on [UO2(L1)(DMSO)], [UO2(L2)], [UO2(L2)(DMSO)] and [UO2(L3)] show relatively short U-O bonds to the benzoylic oxygen atoms between 2.273(6) and 2.368(5) Å. This suggests a preference of these donor sites of the ligands over their imino and amine functionalities (U-N bond lengths: 2.502(7)-2.671(7) Å). The addition of a sixth ligand to the equatorial coordination sphere results in a lengthening of the metal-pyridine bonds. 相似文献
13.
Majdah R. Alotaibi Mohammed Monier NadiaH. Elsayed 《Journal of molecular recognition : JMR》2020,33(2)
Au (III) ion‐imprinted mesoporous silica particles (Au‐Si‐Py) was manufactured by the condensation reaction of (3‐Aminopropyl)triethoxysilane (AT)and 2‐pyridinecarboxaldehyde (Py). The obtained AT‐Py Schiff base ligand was then coordinate with the template gold ions and the polymerizable gold‐complex was allowed to gel in presence of tetraethoxysilane (TEOS) and then the coordinated gold ions were leached out of the obtained silica matrix using acidified thiourea solution. During the synthetic steps, the obtained materials were investigated utilizing advanced instrumental and spectral methods. Moreover, the morphological structure of both Au (III) ions imprinted Au‐Si‐Py and non‐imprinted NI‐Si‐Py silica particles were visualized using scanning electron microscope (SEM). Various adsorption experiments had been carried out using both Au‐Si‐Py and NI‐Si‐Py to examine their potential for selective extraction of gold ions under different conditions 相似文献
14.
Chohan ZH Farooq MA Scozzafava A Supuran CT 《Journal of enzyme inhibition and medicinal chemistry》2002,17(1):1-7
Schiff bases derived from oxaldiamide/oxalylhydrazine and pyrrol-2-carbaldehyde, or salicylaldehyde respectively, as well as their Zn(II) complexes have been prepared and tested as antibacterial agents. These Schiff bases function as tetradentate ligands, forming octahedral Zn(II) complexes. The ketonic form for the diamide derived Schiff base and the enolic form of the hydrazide derived Schiff base were the preferred tautomers for coordination of the metal ions. The title compounds and their Zn(II) derivatives were evaluated for antibacterial activity against several bacterial strains which easily develop resistance to classical antibiotics, such as Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa. Some of them showed promising biological activity in inhibiting the growth of such organisms. 相似文献
15.
Cobalt(III) Schiff base complexes have been used as potent inhibitors of protein function through the coordination to histidine residues essential for activity. The kinetics and thermodynamics of the binding mechanism of Co(acacen)(NH(3))(2)Cl [Co(acacen); where H(2)acacen?is?bis(acetylacetone)ethylenediimine] enzyme inhibition has been examined through the inactivation of matrix metalloproteinase?2 (MMP-2) protease activity. Co(acacen) is an irreversible inhibitor that exhibits time- and concentration-dependent inactivation of MMP-2. Co(acacen) inhibition of MMP-2 is temperature-dependent, with the inactivation increasing with temperature. Examination of the formation of the transition state for the MMP-2/Co(acacen) complex was determined to have a positive entropy component indicative of greater disorder in the MMP-2/Co(acacen) complex than in the reactants. With further insight into the mechanism of Co(acacen) complexes, Co(III) Schiff base complex protein inactivators can be designed to include features regulating activity and protein specificity. This approach is widely applicable to protein targets that have been identified to have clinical significance, including matrix metalloproteinases. The mechanistic information elucidated here further emphasizes the versatility and utility of Co(III) Schiff base complexes as customizable protein inhibitors. 相似文献
16.
Schiff bases derived from condensation of 2,3-dihydroxybenzaldehyde with various primary amines, such as 1-adamantanamine hydrochloride, 2,6-dimethylaniline, 2,6-diethylaniline and 2,6-diisopropylaniline, react with palladium(II) acetate to give the corresponding bis(N-arylsalicylaldiminato)palladium(II) complexes. These complexes have been found to be active catalyst precursors for the Suzuki-Miyaura cross-coupling of aryl bromides and iodides with aryl boronic acids using water as a solvent. 相似文献
17.
The chemiluminescence (CL) phenomena of lanthanide (Ln) ions and their coordinate complexes in peroxomonosulfate system and the energy transfer mechanism during the process were investigated in this work. A strong and sharp CL signal was yielded when the Eu(III) or Tb(III) solution was added to the peroxymonosulfate solution. The CL intensity was greatly enhanced by 2,6‐pyridinedicarboxylic acid (DPA) ligand [maximum enhancement reached when Ln(III):DPA was 1:1] and hexadecyltrimethylammonium chloride micelles. The degree of enhancement of DPA and micelles on Ln(III) CL was related to the fluorescence lifetimes of Ln(III) in different media. According to the ESR spin‐trapping experiments of 2,2,6,6‐tetramethyl‐4‐piperidone and the specific quenching experiments of 1,4‐diazabicyclo[2.2.2]octane and sodium azide, singlet oxygen was generated though the Ln(III) ion‐catalyzed decomposition of peroxymonosulfate. From the comparisons of the fluorescence and CL spectra, lanthanide ions were the luminescence emitter and the ligand DPA absorbed the energy from singlet oxygen and transferred it to Ln(III) ions in the coordinate complexes. Micelles can enhance the CL intensity by improving intermolecular energy transfer efficiencies, removing the quenching effect of water and prolonging the lifetime of singlet oxygen. Copyright © 2009 John Wiley & Sons, Ltd. 相似文献
18.
Wanda Radecka-Paryzek Izabela Pospieszna-Markiewicz Maciej Kubicki 《Inorganica chimica acta》2007,360(2):488-496
The unprecedented self-assembled formation of a two-dimensional salicylaldimine lanthanum coordination polymer is proved by the X-ray diffraction analysis of new lanthanum(III) nitrate complex containing the N,N′-bis(salicylidene)-1,4-butanediamine ligand L, which was prepared in situ through one-step template [2+1] Schiff base condensation of salicylaldehyde with 1,4-butanediamine in the presence of lanthanum(III) nitrate ion and characterized by spectroscopic (IR, ESI-MS, UV-Vis, and 1H NMR) data and microanalysis. The complex displays an infinite [La2L4(NO3)6]∞ polymeric structure based on networks of ten-coordinated La(III) nodes linked by bridging L ligands. The coordination geometry around the lanthanum is a distorted bicapped dodecahedron. This polymer can be described as composed from the columns of dimers connected into chains, via the flexible chain parts of ligands. 相似文献
19.
Zahid H. Chohan M.A. Farooq Andrea Scozzafava Claudiu T. Supuran 《Journal of enzyme inhibition and medicinal chemistry》2013,28(1):1-7
Schiff bases derived from oxaldiamide/oxalylhydrazine and pyrrol-2-carbaldehyde, or salicylaldehyde respectively, as well as their Zn(II) complexes have been prepared and tested as antibacterial agents. These Schiff bases function as tetradentate ligands, forming octahedral Zn(II) complexes. The ketonic form for the diamide derived Schiff base and the enolic form of the hydrazide derived Schiff base were the preferred tautomers for coordination of the metal ions. The title compounds and their Zn(II) derivatives were evaluated for antibacterial activity against several bacterial strains which easily develop resistance to classical antibiotics, such as Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa. Some of them showed promising biological activity in inhibiting the growth of such organisms. 相似文献
20.
Two novel monomeric [C18H17Cl3N2O2Fe] (1) and dimeric [C38H36N4O4Cl6Fe2] (2) Fe(III) tetradentate Schiff base complexes have been synthesized and their crystal structures have been determined by single crystal X-ray diffraction analysis. In complex (1) the Schiff base ligand coordinates toward one iron atom in a tetradentate mode and each iron atom is five coordinated with the coordination geometry around iron atom which can be described as a distorted square pyramid. The presence of a short (2.89 Å) non-bonding interatomic Fe···O distances between adjacent monomeric Fe(III) complexes results in the formation of a dimer. Structural analysis of compound (2) shows that the structure is a centrosymmetric dimer in which the six coordinated Fe(III) atoms are linked by μ-phenoxo bridges from one of the phenolic oxygen atoms of each Schiff base ligand to the opposite metal center. The variable-temperature (2-300 K) magnetic susceptibility (χ) data of these two compounds have been investigated. The results show that for both complexes Fe(III) centers are in the high spin configuration (S = 5/2) and indicate antiferromagnetic spin-exchange interaction between Fe(III) ions. The obtained results are briefly discussed using magnetostructural correlations developed for other class of iron(III) complexes. 相似文献