- Synthesis, vibrational spectral and nonlinear optical studies of N-(4-hydroxy-phenyl)-2-hydroxybenzaldehyde-imine: A combined experimental and theoretical investigation
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The study of imine-bridged organics has been the one hot spot of photo-responsive material sciences in recent years. Herein we make a study of the synthesis, characteristics and potential application of N-(4-hydroxy-phenyl) -2-hydroxy-benzaldehyde-imine (
- Wang, Yufeng,Yu, Zongxue,Sun, Yuxi,Wang, Yishi,Lu, Lude
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- Theoretical and experimental investigations of complexation with BF3.Et2O effects on electronic structures, energies and photophysical properties of Anil and tetraphenyl (hydroxyl) imidazol
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The novel compounds (E)-2-(((4-hydroxyphenyl)imino)methyl)phenol, Tetraphenyl (hydroxyl) imidazole and their corresponding Boron difluoride complexes were synthesized and characterized by spectroscopic techniques. Density functional theory calculations at
- Chaabene, Marwa,Agren, Soumaya,Allouche, Abdul-Rahman,Lahcinie, Mohamed,Ben Chaabane, Rafik,Baouab, Mohamed Hassen V.
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- The benzoxazine compounds, its manufacturing method and a benzoxazine resin
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The present invention provides a novel benzoxazine compound represented by formula (1), from which a highly heat-resistant cured product can be obtained. The present invention also provides a method for producing a benzoxazine compound, the method includi
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Paragraph 0054-0056
(2021/06/03)
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- Synthesis of some novel mixed ligand complexes of Ni(II) and their characterization
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A new series of metal complexes were prepared by refluxing nickel chloride with hot methanolic solution mixture of 8-Hydroxyquinoline and Schiff bases(L1-L6). Schiff base ligands were synthesised by the condensation of 4-aminopheno,
- Riaz, Mohd,Saleem, Mohd
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p. 1152 - 1157
(2021/11/17)
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- Synthesis and molecular docking studies of imines as α-glucosidase and α-amylase inhibitors
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Imine functionality is found in many compounds with important biological activity. Thus, the development of novel synthetic approaches for imines is important. In this work, it is propose an easy, eco-friendly and straightforward synthesis pathway of aryl imines under microwave irradiation catalyzed by Alumina-sulfuric acid. In addition, the in vitro enzymatic inhibition, antioxidant activity and molecular docking studies were performed. The aryl imines were isolated with yields in the range of 37–94%. All aryl imines synthesized were evaluated for in vitro inhibitory potential against α-glucosidase and α-amylase enzymes and the results exhibited that the most of the compounds displayed inhibitory activity against both enzymes. The (E)-1-(4-nitrophenyl)-N-(pyridin-2-yl)methanimine (3d) was 1.15-fold more active than acarbose against α-amylase whilst the (E)-1-phenyl-N-(pyridin-2-yl)methanimine (3c) displayed similar activity that acarbose against α-glucosidase. The molecular docking studies in α-glucosidase and α-amylase reveal that aryl imines mainly establish an H-bond with the R2-subtituent and hydrophobic interactions with the R1-subtituent. The docking analysis reveals these synthetic aryl imines 3d-i interact in same active site than acarbose drug in both enzymes.
- Aispuro-Pérez, Analy,Bastidas, Pedro,Calderón-Zamora, Loranda,García-Páez, Fernando,López-ávalos, Juan,Monta?o, Sarita,Montes-Avila, Julio,Ochoa-Terán, Adrián,Osuna-Martínez, Ulises,Picos-Corrales, Lorenzo A.,Sarmiento-Sánchez, Juan I.
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- Facile synthesis, solublization studies and anti-inflammatory activity of amorphous zinc(Ii) centered aldimine complexes
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In this study, Zn(II) centered complexes with aldimine derivatives were synthesized using green solvent, polyethylene glycol (PEG-400) and amorphous complexes were characterized by FT-IR, multinuclear (1H and13C NMR), elemental and thermal analysis. Thermogravimetric analysis indicated the extended thermal stability of the synthesized complexes. All the Zn(II) complexes show very significant photoexcitation in the range of 318 – 384 nm and photoemission in the range of 502 – 562 nm. Among all the complexes, Zn(II) complex (3Zn) showed minimum band gap value, 2.35 eV. These amorphous complexes have been reported for their wide applications in biomedical sciences. The synthesized aldimine ligands and Zn(II) complexes were investigated for anti-inflammatory activity and these complexes showed more anti-inflammatory potential than the corresponding aldimine ligands. The solubilization of zinc complexes in sodium dodecyl sulphate was also investigated to reveal the interaction of metal complexes by using UV-Visible spectroscopy and electrical conductivity measurements.
- Ali, Uzma,Alshater, Heba,Imran, Muhammad,Maalik, Aneela,Noor, Sadia,Qureshi, Ahmad Kaleem,Raheel, Ahmad,Sharif, Muhammad,Taj, Muhammad Babar,Tirmizi, Syed Ahmad
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p. 929 - 941
(2021/06/26)
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- 1,3,5-TRIAZINE-CONTAINING BENZOXAZINE AND PREPARATION METHOD, CURABLE COMPOSITION AND CURED PRODUCT THEREOF
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The present invention relates to a 1,3,5-triazine-containing benzoxazine compound, and preparation method, curable composition and cured product thereof. The compound of the present invention has an improved storage stability, and the cured product has an
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- The scavenging of DPPH, galvinoxyl and ABTS radicals by imine analogs of resveratrol
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Resveratrol (3,5,41-trihydroxystilbene) is a phytoalexin produced by plants. Resveratrol is known for its anti-cancer, antiviral and antioxidant properties. We prepared imine analogs of resveratrol ((hydroxyphenyliminomethyl)phenols) and tested their anti
- Kotora, Peter,?er?ěn, Franti?ek,Filo, Juraj,Loos, Du?an,Gregáň, Juraj,Gregáň, Fridrich
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- A study on the co-reaction of benzoxazine and triazine through a triazine-containing benzoxazine
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To study the co-reaction of benzoxazine and triazine, a triazine-containing benzoxazine (P-tta) was prepared through nucleophilic substitution of 4-(2H-benzo[e][1,3]oxazin-3(4H)-yl)phenol (P-ap) with 2,4,6-trichloro-1,3,5-triazine. DSC thermograms show th
- Lin, Ching Hsuan,Chou, Yu-Chun,Wang, Meng Wei,Jeng, Ru Jong
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p. 17539 - 17545
(2016/02/23)
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- Experimental and theoretical study of antioxidative properties of some salicylaldehyde and vanillic Schiff bases
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The antioxidative capacity and structure-activity relationships of ten Schiff bases were investigated experimentally and theoretically. All compounds contain the aniline moiety, while the aldehyde part is either salicylaldehyde or vanillin. The DPPH assay was used to test the potential antioxidative activity of these compounds, and DFT study was used to investigate their electronic structures and provide insight into their structure-activity relationships. The effect of the position of the hydroxy, as well other groups present, on the antioxidative activity was examined. The possible radical scavenging mechanism was determined in polar (water and methanol), and nonpolar (benzene) solvents. Based on the experimental and computational results, compounds 7 and 8 exhibit the highest radical scavenging properties.
- Petrovi?, Zorica D.,Orovi?, Jelena,Simijonovi?, Du?ica,Petrovi?, Vladimir P.,Markovi?, Zoran
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p. 24094 - 24100
(2015/03/30)
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- Synthesis and characterization of ion-imprinted resin for selective removal of UO2(II) ions from aqueous medium
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In this work, uranyl ion-imprinted resin based on 2-(((4-hydroxyphenyl)amino)methyl)phenol was synthesized by condensation polymerization of its uranyl complex in presence of resorcinol and formaldehyde cross-linkers. Numerous instrumental techniques incl
- Monier,Alatawi, Raedah A. S.,Abdel-Latif
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p. 306 - 315
(2015/04/27)
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- Substituent effects on the absorption and vibrational spectra of some 2-hydroxy Schiff bases: DFT/TDDFT, natural bond orbital and experimental study
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The electronic structure of salicylideneaniline (SA) and some of its derivatives are investigated both experimentally and theoretically. The equilibrium geometric structures of the studied compounds are determined at the B3LYP/6-311++Glevel of theory. A set of 12 substituted SA derivatives is considered in the present work. The choice of these substituents aims to create a push-pull system on the SA basic structure which would shade light onto its photo physics. The electronic absorption spectra of SA are recorded in the UV-VIS region, in both polar and nonpolar solvents. Assignments of the observed electronic transitions are facilitated via time-dependent density functional theory (TDDFT) computations at the same level of theory. Electronic configurations contributing to each excited state are identified and the relevant MOs are characterized. The extent of delocalization and intramolecular charge transfer are estimated and discussed in terms of natural bond orbitals (NBO) analysis and second order perturbation interactions between donor and acceptor MOs. Solvent effects on the electronic absorption spectra are discussed in terms of the difference in polarizabilities of the ground and excited states. FTIR spectra of SA and its derivatives are measured in KBr platelets. Detailed vibrational assignments are given based on the calculated potential energy distributions. "IR marker bands" that characterize the SA framework are identified. The effect of substituents, the nature of the characteristic "marker bands", and intensity quenching of some bands are discussed.
- Elroby,Aboud,Aziz,Hilal
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p. 414 - 427
(2015/08/06)
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- Synthesis and Characterization of Cyanate Ester Functional Benzoxazine and Its Polymer
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The first benzoxazine incorporating cyanate ester group in its structure has been synthesized. The polymerization process investigated by differential scanning calometry (DSC) exhibits two clearly separated exotherm maxima, corresponding to cyanate ester
- Ohashi, Seishi,Kilbane, John,Heyl, Tyler,Ishida, Hatsuo
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p. 8412 - 8417
(2015/12/12)
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- Design, synthesis and biological evaluation of imine resveratrol derivatives as multi-targeted agents against Alzheimer's disease
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A series of imine resveratrol derivatives (1-20) have been designed, synthesized, and evaluated as multi-targeted compounds for the treatment of Alzheimer's disease (AD). In vitro studies show that most of the molecules exhibit a significant ability to in
- Li, Su-Yi,Wang, Xiao-Bing,Kong, Ling-Yi
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- An efficient catalyst for the synthesis of schiff bases
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An efficient high yielding synthesis of Schiff bases (1-17) is derived from condensation of 2-fluorenamine and 4-amino phenol with a variety of aldehydes catalyzed by dodecatungstosilicic acid / P2O5 under solvent free conditions at room temperature. The catayst is found to be more efficient in terms of ease of reaction workup and high yields. This methodology contributes to an energy efficient, facile and environamental friendly synthesis for the preparation of Schiff bases. The structures of afforded Schiff bases were characterized by spectroscopic data and elemental analysis.
- Fareed, Ghulam,Versiani, Muhammad Ali,Afza, Nighat,Fareed, Nazia,Kalhoro, Mahboob Ali,Yasmeen, Shazia,Anwar, Muhammad Aijaz
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p. 426 - 430
(2013/07/27)
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- Concise synthesis and characterization of unsymmetric 1,3-benzoxazines by tandem reactions
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A new synthetic protocol for the preparation of unsymmetric 1,3-bisbenzoxazines using the combination of three-step synthesis and classical one-step benzoxazine synthesis strategies is described. For this purpose, 4-hydroxyphenylaminomethyl phenol (HPAMP)
- Imran, Muhammad,Kiskan, Baris,Yagci, Yusuf
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supporting information
p. 4966 - 4969
(2013/09/02)
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- The antioxidant effect of imine resveratrol analogues
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Twenty five Imine resveratrol analogues (IRAs) were synthesized, replacing the CC bond in resveratrol with CN bond, as well as substitution modifications on aromatic rings. Radical scavenging activities against DPPH, along with singlet oxygen quenching capacities were evaluated, and further confirmed using density functional theory calculations (DFT). It was found that IRAs bearing ortho-OH on B ring have better radical scavenging activities against DPPH than resveratrol, these compounds were also found to be effective 1O 2 quenchers. Theoretical studies on the reaction mechanism of these compounds with 1O2 suggest that the 1,3-addition to a double bond with a -OH group with the formation of allylic hydroperoxide is the most probable reaction route.
- Lu, Jing,Li, Chang,Chai, Yun-Feng,Yang, De-Yu,Sun, Cui-Rong
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supporting information; experimental part
p. 5744 - 5747
(2012/09/22)
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- Antioxidant activity of synthetic resveratrol analogs: A structure-activity insight
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This study evaluated the antioxidant activity of five resveratrol analogs using the DPPH method. The molecules activity was related with their chemical structure. Besides descriptive statistics, the analysis of variance (ANOVA) followed by Tukey's post hoc test were performed (p50 value statistically different from the resveratrol (p0.001), its antioxidant activity was considered satisfactory. The other analogs (D and E), which have a 4-acid grouping in place of 4-hydroxy grouping, showed lower antioxidant activity than resveratrol (p0.001). Further studies to address possible advantages of analogs in relation to resveratrol should be conducted in order to make them feasible for therapeutic use.
- Calil, Natalia Oliveira,De Carvalho, Gustavo Senra Goncalves,Da Silva, Annelisa Farah,Da Silva, Adilson David,Raposo, Nadia Rezende Barbosa
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scheme or table
p. 676 - 679
(2012/09/22)
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- Synthesis, antioxidant and antibacterial activities of some Schiff bases containing hydroxyl and methoxy groups
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A series of Schiff bases were synthesized from different aromatic amines and aromatic aldehydes containing hydroxyl and methoxy groups. These compounds were characterized by IR and 1H NMR. All the compounds were screened for in vitro antioxidant activity using DPPH method and total reducing power activity based on the ability of compounds to reduce the Fe3+-TPTZ complex to the Fe2+/ferrous. Compounds substituted with hydroxyl and other electron donating groups, such as, methoxy groups showed low to high antioxidant activity. In addition, the compounds have been screened for their antibacterial activity against strains of Escherichia coli, Methycillinresistant Staphylococcus aureus, Klebsiella pneumonia and Pseudomonas aeruginosa. The tested Schiff bases at 5 mg/disc showed different antibacterial activities depending on the type of the tested bacterial species. However, E. coli appeared to be sensitive to seven compounds (Ia, Ib, Ic, Id, If, IIb and IIe), while methicillin resistant Staphylococcus aureus (MRSA) was affected by Ic, Ie, IIc and IIe compound. On the other hand, the compounds Ia, Ic, Id, Ie and IIh revealed antibacterial activity against Klebsiella spp. The Pseudomonas aeruginosa was not sensitive to any of the tested Schiff bases.
- Al-Mamary, Mohammed,Abdelwahab, Siddig Ibrahim,Ali, Hapipah Mohd,Ismail, Salma,Abdulla, Mahmood Ameen,Darvish, Pouya
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experimental part
p. 4335 - 4339
(2012/09/07)
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- Antioxidant activities and transition metal ion chelating studies of some hydroxyl Schiff base derivatives
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Several hydroxyl Schiff base (HSB) compounds (1-10) with good radical scavenging activity (RSA) were designed. Compounds 6, 7, and 10 showed better RSAs than the common synthetic antioxidant 2,6-diterbutyl- 4-methylphenol (BHT) in DPPH and ABTS assays. To probe whether these HSB compounds may exert their antioxidant effect through transition metal ion chelation, the copper and ferrous chelating abilities of them were investigated. It was found by fluorescence quenching spectra that the binding constants Ka were in the range of 0.85×103-7.30×104 M-1. Further study was carried out by the complexation of a representative compound 5 with ferrous ion in mass spectrum. A 2:1 5-ferrous complex was readily formed in a methanol-water solution (v:v, 8:2), which confirmed that the chelation happened when the HSB compounds were treated with transition metal ions. The above results indicated that the transition metal ion chelation play an important role in their antioxidant abilities. Springer Science+Business Media, LLC 2011.
- Zhang, Ye,Zou, Biqun,Wang, Kai,Pan, Yingming,Liang, Hong,Yi, Xianghui,Wang, Hengshan
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experimental part
p. 1341 - 1346
(2012/08/27)
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- Hydrogen bonding in Schiff bases - NMR, structural and experimental charge density studies
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A series of sixteen Schiff bases (derivatives of salicylaldehydes and aryl amines) was studied to reveal the influence of substituents and the length of the linker on the properties of the H-bonding formed. In theory, two groups of compounds, derivatives of 2-(2-hydroxybenzylidenoamine)phenol) and 2-hydroxy-N-(2-hydroxybenzylideno)benzylamine, can form different types of H-bonds using one or two hydroxyl groups present in the molecules. Two other groups of compounds, derivatives of 4-(2-hydroxybenzylidenoamine)phenol and N-(2-hydroxybenzyideno)benzylamine, can form only one type of H-bond. It was confirmed by 15N and 13C NMR experiments, that in all cases only traditional, H-bonded six-membered chelate rings were formed. The positions of the hydrogen atom in the rings depend on the substituent and phase. Generally, the OH H-bond form dominates in solution, with exception of the nitro derivatives, where the NH tautomer is present. In the solid state the tautomeric equilibrium is strongly shifted to the NH form. Only for the 5-Br derivative of one compound was the reverse relationship found. According to the results of experimental charge density investigations, two intramolecular H-bonds in the 5-methoxy derivative of 2-hydroxy-N-(2′-hydroxybenzylideno) benzylamine) differ significantly in terms of charge density properties. The intra- and intermolecular H-bonds formed by the deprotonated oxygen atom from 2-OH group are strong, with significant charge density concentration at the bond critical point and a straight, well-defined bond path, whereas the second intramolecular H-bond formed by the oxygen atom from the 2′-OH group is quite weak, with ca. five times smaller charge density concentration than in the previous case and a bent bond path. In terms of energy densities, the latter H-bond appears to be a non-bonding interaction, with total energy density being slightly positive. In terms of source contributions to the density at the H-bond critical point from the atoms involved, the intermolecular, linear H-bond is very strong and charge-assisted in the source function classification, the N(1)-H(1N)...O(1) H-bond is medium-strength, while the third H-bond is extremely weak.
- Makal, Anna,Schilf, Wojciech,Kamienski, Bohdan,Szady-Chelmieniecka, Anna,Grech, Eugeniusz,Wozniak, Krzysztof
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supporting information; experimental part
p. 421 - 430
(2011/02/23)
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- Spectral investigation of the activities of amino substituted bases
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Three new series of biologically active amino substituted Schiff bases with general formula, R1N=CHR2. Here R1 = 2-amino-benzthiazole, 4-amino-salicylic acid and 4-aminophenol. R 2=4-chloro-benzaldehyde, 2-chloro-benzaldehyde, salicylaldehyde, vanillin and benzaldehyde were synthesized by the reaction of three different amino substituted compounds and substituted aldehydes in ethanol. Such compounds were characterized by different physico-chemical techniques like, melting point, elemental analysis, multinuclear nmr (1H, 13C). The free ligands and their metal complexes have been screened for their in vitro biological activities against bacteria, fungi and yeast. The metal complexes show more potent activities compared with Schiff base ligands.
- Ashraf, Muhammad Aqeel,Wajid, Abdul,Mahmood, Karamat,Maah, Mohd. Jamil,Yusoff, Ismail
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experimental part
p. 363 - 372
(2012/04/04)
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- Synthesis, spectral investigation (1H, 13C) of new (N, O and S based) schiff bases and evaluation of their antimicrobial activities
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Three new series of biologically active amino substituted Schiff bases (1-12) with general formula, R1N=CHR2 (R1 = 2-amino-benzthiazole, 4-amino-salicylic acid and 4-aminophenol; R2 = benzaldehyde, 2-chloro-benzaldehyde, 4-chloro-benzaldehyde, salicylaldehyde and vanillin) were synthesized by the reaction of three different amino substituted compounds and substituted aldehydes in ethanol. The synthesized compounds were characterized by different physico-chemical techniques like, melting point, elemental analysis, multinuclear nmr (1H, 13C). The compounds were subjected for bioassay screening and showed promising antibacterial and antifungal activities using Amoxicillin and Ciprofloxacin as standard drugs.
- Khosa, Muhammad Kaleem,Chatha, Shahzad Ali Shahid,Nisar, Madhia,Zia, Khalid Mahmood,Khalil-Ur-Rehman,Jamal, Muhammad Asghar,Yousaf, Muhammad
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experimental part
p. 421 - 425
(2012/04/17)
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- Methyltrioxorhenium-catalyzed oxidation of pseudocumene for vitamin e synthesis: A study of solvent and ligand effects
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Vitamin E is an essential food component of major economical relevance with important antioxidant properties and biological activity. The oxidation of pseudocumene to trimethyl-1,4-benzoquinone would be a key transformation in an alternative industrial production of α-tocopherol that is important for the antioxidant activity of vitamin E. The methyltrioxorhenium (MTO)-catalyzed oxidation of pseudocumene has been revisited to offer a more environmentally friendly, economically beneficial and milder approach to this important industrial product. It has been observed that by choosing the solvent and Lewis base additives (as ligands of MTO), both yield and chemoselectivity are considerably improved, allowing milder reaction conditions compared to previously reported protocols.
- Carril, Monica,Altmann, Philipp,Drees, Markus,Bonrath, Werner,Netscher, Thomas,Schuetz, Jan,Kuehn, Fritz E.
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experimental part
p. 55 - 67
(2011/11/30)
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- Evaluation of antibacterial activity of some Schiff bases
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From 4-amino phenol, some Schiff bases were synthesized. By IR and NMR spectral data, the structural characterization of these synthesized compounds were done. The antibacterial activity of all these synthesized Schiff bases was studied against B. cereus-ATCC 11778, P. aero-ATCC 27853, E. coli-ATCC 25922, K pneu-NCIM 2719 and 5. aureus-ATCC 25923, by agar ditch method in dimethyl formamide and dimethyl sulfoxide. It is observed that antibacterial activity depends on the molecular structure of Schiff base, solvent used and bacterial strain under consideration. Out of two solvents studied, dimethyl formamide is proved to be best and salicylaldehyde as side chain to 4-amino phenol could be used as lead molecule in drug designing i.e. in inhibiting above bacterial strains.
- Baluja, Shipra,Parikh, Jigna,Chanda, Sumitra,Vaishnani
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experimental part
p. 1338 - 1342
(2010/08/05)
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- Synthesis, characterization, and reactivity of Pd(II) salicylaldimine complexes derived from aminophenols
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Schiff bases, derived from the condensation of salicylaldehydes with 3- and 4-aminophenol, reacted with palladium(II) acetate to give the corresponding bis(N-arylsalicylaldiminato)palladium(II) complexes. These complexes have been found to be active catalysts for the Suzuki-Miyaura cross-coupling of aryl bromides and iodides with aryl boronic acids, using water as a solvent.
- Tardiff, Bennett J.,Smith, Joshua C.,Duffy, Stephen J.,Vogels, Christopher M.,Decken, Andreas,Westcott, Stephen A.
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p. 392 - 399
(2008/03/15)
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- Facile preparation of [4.4]metacyclophane- and [5.5]paracyclophane-type macrocycles from arylboronic acids and salicylideneaminoaryl alcohols
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Four different salicylideneaminoaryl alcohols have been treated with arylboronic acids in order to prepare air-stable cyclophane-type macrocyclic systems. In two cases, this objective could be realized with the high-yield formation of [4.4]metacyclophane
- Sanchez, Mario,Hoepfl, Herbert,Ochoa, Maria-Eugenia,Farfan, Norberto,Santillan, Rosa,Rojas-Lima, Susana
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p. 612 - 621
(2007/10/03)
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- Benzylideneaniline derivatives
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This invention describes a method of treating inflammation in warm blooded animals by topically administering an effective amount of benzylideneaniline or its derivatives.
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- Indium(III) Complexes with Some Salicylidene Aromatic Schiff Bases
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In(III) complexes with salicylidene aromatic Schiff bases have been prepared.The nature of the complexes has been studied by microanalysis of the solid complexes, conductometric titration, uv and ir spectrophotometric measurements.The complexes are of the type 1:1 and 2:1 depending upon the Schiff base.The tendency of the salicylidene Schiff base molecule towards complex formation with In(III) is found to depend largely on the strength of the intramolecular hydrogen bond established between the aldehydic OH group and C=N.Furthermore, it is concludedthat these Schiff bases cordinate to In(III) as tri- or bidentate ligands depending upon the molecular structure of the Schiff base (not as monodentate ligand as previously described).The high molar absorbance of the 1:2 In(III) complex with salicylidene-o-hydroxyaniline I (17800 mol-1cm2) can be applied for the microdetermination of small amounts of Indium as low as 0.57 μg/ml solution. - Keywords: Indium(III) complexes; Schiff bases
- Mahmoud, M.R.,Issa, I.M.,El-Gyar, S.A.
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p. 431 - 438
(2007/10/02)
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