Vol 2, No 4 (2011)

December 2011

Table of Contents

Editorial

Hakan Arslan
DOI 10.5155/eurjchem.2.4.i-i.546
Editorial Board
i-i
Hakan Arslan
DOI 10.5155/eurjchem.2.4.ii-viii.547
Graphical Contents
ii-viii

Research Article

Tatiana Besset, Emmanuelle Braud, Rafika Jarray, Christiane Garbay, Stephanie Kolb, Pierre-Marc Leo, Christophe Morin
DOI 10.5155/eurjchem.2.4.433-440.400

A set of new heteroquinone derivatives bearing two methoxycarbonylmethylthio groups on the benzoquinone ring were synthesized and evaluated for CDC25B phosphatase inhibitory activity. All compounds inhibited the enzyme with IC50 values in the micromolar range regardless of the size and heteroatoms constituting the heterocycle fused to the quinone ring. Moreover, these quinonoid-based compounds showed moderate antiproliferative activity toward two cancer cell lines (HeLa and MiaPaca-2). These results provide additional data for CDC25 inhibition by quinone-type derivatives and highlight the importance of substituents on the quinonic moiety.

2_4_433_440_800

433-440
Marta Huebra, Maria Puy Elizalde
DOI 10.5155/eurjchem.2.4.441-447.417

The electrochemical behaviour of the reagent 4-chloro-N-8-quinolinylbenzenesulfonamide has been studied by sampled direct current and differential pulse polarography as well as by cyclic voltamperometry techniques. Three reduction waves are obtained and the reversibility and nature of the electrodic processes are discussed. The first and third reduction waves have been explained through chemical reactions and adsorption processes involving the interaction with mercury as electrodic material, whereas the second wave is attributed to the reduction process of the reagent itself. Acidity constant values of the compound in 0.1 M KCl / 25 % methanol medium through polarographic measurements are also given. The influence of the addition of copper to the hydroalcoholic solution in the electrochemical reduction of the reagent is also described.

2_4_441_447_800

441-447
Nazmul Islam
DOI 10.5155/eurjchem.2.4.448-454.94

A new atomic electronegativity scale is proposed by using the essence of electronegativity definitions of Gordy and Mulliken. The new computed atomic electronegativity data is found to satisfy all the sine qua non of a reasonable scale of atomic electronegativity. The electronegativity data is used to compute some useful descriptors of chemical reactivity. Comparative studies reveal that the new approach to derive the Gordy’s scale of electronegativity is a successful venture.

2_4_448_454_800

448-454
Khairy Abdel Hameed Mohsen El-Bayouki, Wahid Mohamed Basyouni, Yahia Abdel Fatah Mohamed, Mohsen Mohamed Aly, Samir Youssef Abbas
DOI 10.5155/eurjchem.2.4.455-462.171

Novel 4(3H)-quinazolinone derivatives with biologically active moieties were synthesized. Reactions of 2-cyano-N-(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl) acetamide with carbon disulfide, isothiocyanates followed by cycloalkylation afforded acrylamide, 1,3-dithiazole, 1,3-dithiane, thiazole and pyrazole derivatives. The 2-pyridone derivatives were obtained via reaction of cyanoacetamide with some acetylacetone or arylidenes. Cyclocondensation reaction of cyanoacetamide with o-hydroxy aldehydes furnished chromene derivatives. Screening for some selected compounds was carried for their potential antitumor and antifungal activities. 2-Cyano-N-(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl)-2-(4-methyl-3-phenyl-thiazol-2(3H)ylidene)-acetamide with 3-side chain incorporated with substituted thiazole moiety was found to be of high to moderate activity towards cells. Also, the latter product showed high activity against Aspergillus ochraceus Wilhelm with inhibition zone (18 mm) compared with (20 mm) Nystatin inhibition zone.

2_4_455_462_800

455-462
Hossein Eshghi, Zahra Alishahi, Mahmood Zokaei, Aboulfazl Daroodi, Elahe Tabasi
DOI 10.5155/eurjchem.2.4.463-468.425

In order to screen dye decolorization by Trametes hirsuta, Trametes gibbosa and new fungus Trichaptum biforme, Methylene Blue (MB), Methyl Green (MG) and Reactive Black 5 (RB5) were studied in Broth culture at concentrations of 25, 50 and 70 ppm. Decolorization of these three kind dyes by T. hirsuta decreased by increasing of concentration. Decolorization of RB5 by T. hirsuta was examined in two different medium contains of Mn2+ or veratryl alcohol (VA), as activators. At the presence of laccase activator (VA), RB5 was decolorized 91% at concentration of 70 ppm, and in the medium contains of MnP activator (Mn2+), dye was decolorized less than 50% at same concentration. Decolorization of RB5 by T. hirsuta was more than decolorization of dye at the presence of MnP activator (Mn2+). T. gibbosa decolorized MB, MG and RB5 more than 80% in the presence of MnP activator. Decolorization of the three kind dyes by T. gibbosa, was independent of concentration. T. gibbosa decolorized different dyes during 20 days and T. hirsuta did it during 32 days, this is due higher potential of decolorization of synthetic dyes for T. gibbosa than T. hirsuta. Decolorization of MB by new fungus T. biforme was studied in two medium contains of MnP activator and laccase activator. Rate of decolorization in the presence of MnP activator was more than decolorization in the presence of laccase activator. Decolorization of MB by new fungus T. biforme was higher than decolorization of MB by two other fungi.

2_4_463_468_800

463-468
Bahjat Ali Saeed, Rita Sabah Elias
DOI 10.5155/eurjchem.2.4.469-474.496

The molecular structure and electronic spectra of eleven dihydropyridones were theoretically studied utilizing density functional (DFT) method. The structures were optimized using B3LYP/6-31G(d,p) level of theory. The conformations of the molecules were analyzed with respect to substituents. The central six-membered dihydropyridone ring adopted a half-chair conformation. The geometries did not differ significantly except for conformations of the phenyl or styryl substituents. The only substituents that affected the structure of the central ring are those which have conjugation overlap with the -C=C-C=O system within the ring. Dipole moments and natural charges were calculated and it was found that in most cases substitution leads to higher dipoles, and both methyl and phenyl substituents have the same effect on the atomic charge distribution leading to decrease the atomic charge on the substitution site. Wiberg bond indices were also calculated and used to analyze the substitution effect on the electronic properties of the molecules. It is concluded that substitution on atoms that are not a part of the N-C=C-C=O system have practically no effect on both structural and electronic properties of the molecules. The electronic spectra were also calculated using the ZINDO method. The predicted spectra are in good agreement with experimental spectra concerning the long wavelength absorption band. The electronic transitions were either pure HOMO to LUMO transitions or comprises components of HOMO to LUMO and other transitions like H-1 to L, H to L+2, H-1 to L+1, H-2 to L+1.

2_4_469_474_800

469-474
Mahmoud Refaee Mahmoud, Hassan Mohamed Fawzy Madkour, Eman Abd El-Fattah El-Bordany, El-Sayed Ahmed Soliman
DOI 10.5155/eurjchem.2.4.475-479.193

5-Arylmethylene-2-imino-4-oxo-2-thiazolidine 3 was obtained as the sole product from the reaction of α-cyano-3,4,5-trimethoxy cinnamonitrile and/or ethyl-α-cyano-3,4,5-trimethoxy cinnamate (1a,b) with 2-imino-4-oxo-2-thiazolidine 2. The reaction of 3 with benzyl amine gave the imidazolidin-4(H)one derivative 4 while with hydrazine hydrate afforded the dimeric product 5. Also, reaction of thiazolidinone derivative 3 with piperidine gave thiazol-4(5H)one derivative 6 which on treatment with Grignard reagent and active methylene compounds afforded thiazolidin-4-one derivatives 7-9, respectively. Compound 6 was converted to the potassium salt 10 which treated with acetic acid, ethyl chloroacetate and furoyl chloride to give the compounds 11-13, respectively. The structures of all new compounds were evidenced by microanalytical data and spectral data.

2_4_475_479_800

475-479
Poomalai Jayaseelan, Selladurai Prasad, Subramanian Vedanayaki, Rangappan Rajavel
DOI 10.5155/eurjchem.2.4.480-484.353

A novel oxime ligand has been synthesized by refluxing 3,3’-diaminobenzedine and phthalaldehyde monoxime. Copper (II), cobalt (II), nickel (II) and manganese (II) binuclear complexes of this ligand have been prepared and characterized by using elemental analysis, molar conductance studies, IR, UV, NMR, EPR and magnetic studies. The molar conductance measurements correspond to a non-electrolytic nature for all complexes which can be formulated as [M2(L)X4] (Where M = Cu(II), Ni(II), Co(II) and Mn(II); X = Cl). The UV-visible spectra of all the complexes are well characterized by broad weak d-d band and a high intensity charge-transfer transition. Thermal studies supported the chemical formation of these complexes showed that they decomposed in three or four stages depending on the type of ligand. The far-IR spectrum confirms the presence of coordinate chloride ion in all the complexes as evidenced by one intense far IR bands around 310-330 cm−1. In electrochemical studies the resulting cyclic voltammogram consists of single quasi-reversible one electron transfer. The ligand and complexes have been screened for their antimicrobial activity against two Gram-positive bacteria, two Gram-negative bacteria and fungi. The binuclear metal complexes were found to possess potent antimicrobial, antifungal activity better than ligand alone.

2_4_480_484_800

480-484
Mohammad Mohsen Sarafraz, Mohammad Jamshidnejad, Ahmad Arabi Shamsabadi, Saeed Laki, Hadi Ajami
DOI 10.5155/eurjchem.2.4.485-488.450

Accuracy of Riazi-Whitson mathematical correlation for estimating the molecular diffusion coefficient in gaseous hydrocarbons has been improved, which decreases the absolute average deviation related to the experimental data using About 486 experimental data points that have been collected from latest existing researches. Likewise, re-optimizing, and statistical calculations have been done to synchronize data to avoid unexpected deviations. As shown in present work, deviation values for results of improved correlation from experimental data are less in compare to Riazi-Whitson original correlation. The absolute average deviations for obtained values of improved correlation are about 9.71%, which is about 14% for original mentioned correlation. The input parameters are molecular weight, critical properties, and acentric factors of components in the system; mixture molar density; low-pressure gas viscosity and actual viscosity. The last three properties are calculable by proper correlations in chemical handbooks.

2_4_485_488_800

485-488
Farah Samih Zeitouni, Gehan Moustafa El-Subruiti, Ghassan Omar Younes, Mohammad Fawzi Amira
DOI 10.5155/eurjchem.2.4.489-494.440

The aquation of bromopentaamminecobalt(III) ion in the presence of ion-pairing malonate anion in mixed solvent media of water with tert-butanol (10%-50%) v/v have been investigated spectrophotometrically at different temperatures (30-60 oC). Nonlinear plots of Log (kip) ion-pair rate constants against the reciprocal of the dielectric constant D, Log of water concentration and Grunwald-Winstein Y values were found. The thermodynamic and extrathermodynamic analyses of the kinetic data have been discussed in terms of solvent effect on the ion-pair aquation reactions. The obtained isokinetic temperatures of these systems indicate the existence of compensation effect arising from solute-solvent interaction. The extrema found in the change of ∆Hip* and ∆Sip*with the mole fraction of the co-solvent can be attributed to the change of the physical properties of the solvent-water mixture with the solvent structure. Application of a free energy cycle is performed to compare between the stability of the initial and the transition state of the complex. However, small changes in ∆Gip*with the mole fraction of the co-solvent was found, indicating a compensating effects between ∆Hip* and ∆Sip*

2_4_489_494_800

489-494
Vijayalakshmi Kunkuma, Lakshmi Anu Prabhavathi Devi Bethala, Yadagiri Bhongiri, Badari Narayana Prasad Rachapudi, Seetharamanjaneya Sai Prasad Potharaju
DOI 10.5155/eurjchem.2.4.495-498.413

Monoammonium salt of 12-tungstophosphoric acid [(NH4)H2PW12O40] catalyst was used for the synthesis of biologically important quinoxaline derivatives in excellent yields from various aromatic 1,2-dicarbonyl and 1,2-diamines. The methodology has the advantages of mild reaction conditions with simple workup procedure, even for the synthesis of quinoxaline derivatives from sterically hindered diamine.

2_4_495_498_800

495-498
Azizollah Nezhadali, Fatemeh Moein Pour
DOI 10.5155/eurjchem.2.4.499-502.461

The competitive metal ion transport of Ag(I), Co(II), Ni(II), Zn(II), Cu(II), Cd(II) and Mn(II) cations with dibenzo-18-crown-6 (DB18C6) were studied and compared. The source phase contained equimolar concentration of the metal cation and the organic phase contained the ligand (DB18C6) in an organic solvent. The concentrations in the all transport experiments for the cations and ligand were 0.01 M and 1.0×10-3 M, respectively. The source phase solutions were buffered (acetic acid/sodium acetate) at pH 4-6. The transports of Cu(II), Ag(І) and Co(II) with DB18C6 are possible in the mixture, but the transport efficiency for Ag(І) ion is much better than the other cations. The presence of dichloromethane and 1,2 dichloroethane were optimized in the organic phase. The results show the transport efficiency depends to the types of thiourea and potassium thiocyanate ligands in the receiving phase. The results show that the presence of palmetic acid in the membrane phase improves the efficiency of the transport for Ag(І) cation.

2_4_499_502_800

499-502
Adly Abdella Hanna, Sahar Mohamed Mousa, Marwa Adel Sherief, Gehan Mahmoud Elkomy
DOI 10.5155/eurjchem.2.4.503-508.441

A system of Ce(SO4)2.4H2O, Zn(CH3COO)2.2H2O and phosphoric acid was studied by the chemical reaction between the precursor materials. The cerium cations were replaced by zinc cations (x) in the range of x = 0.0-1.0. The obtained gels were dried and calcinated at 650 oC for 2 hrs. The effect of calcination on the produced phases was studied using X-ray diffraction (XRD) and infrared spectroscopy (IR). The thermal behaviors of only the dried samples were investigated employing differential scanning calorimetric (DSC) and thermogravimetric analysis (TGA). The transmission electron microscope (TEM) was used to investigate the morphology, crystallinity and particle size of both dried and calcined samples. The TEM results indicated that the crystallinity was improved by increasing the zinc contents. The importance of Zn, Ce phosphates return to their using as UV-shielding agents.

2_4_503_508_800

503-508
Mahmoud Abdallah Mohamed, Eman Kamal Ahmad Abdelall, Yasser Hassan Zaki, Abdou Osman Abdelhamid
DOI 10.5155/eurjchem.2.4.509-513.463

pyrazolo[1,5-a]pyrimidine, [1,2,4]triazolo[1,5-a]pyrimidine and pyrimido[1,2-a] benzimidazole derivatives were synthesized by reaction of sodium salt of 3-hydroxy-(1-pyridin-2-yl)prop-2-en-1-one or sodium salt of 3-hydroxy-1-(pyridin-3-yl)prop-2-en-1-one with different heterocyclic amines in piperidenium acetate. Also, 3-amino-6-(2-pyridyl)thieno[2,3-b]pyridine derivatives were synthesized via reaction of pyridine-2-thione with various halogenated compounds. The structures of the newly synthesized compounds were confirmed by elemental analysis, spectral data, X-ray and alternative synthetic routes whenever possible.

2_4_509_513_800

509-513
Mamdouh Adly Hassan, Ahmed Mohamed Mosalem Younes, Mohamed Mobark Taha, Abou-Bakr Haredy Abdel-Monsef
DOI 10.5155/eurjchem.2.4.514-518.479

N-phenylsulphonyloxytetrachlorophthalimide was obtained by treatment of N-hydroxy tetrachlorophthalimide with benzenesulphonyl chloride. Also, the titled compound 3 was obtained by reaction of compound 2 with hydrazine hydrate via Lossen rearrangement. Compound 3 used as starting material for the synthesis of new pyrimidine and quinazolinedione derivatives containing four chlorine atoms which have pharmacological activity.

2_4_514_518_800

514-518
Goutam Mukhopadhyay, Jasmina Khanam, Arunabha Nanda, Nripendra Nath Bala, Won Chun Oh
DOI 10.5155/eurjchem.2.4.519-523.483

The objective of the present study was to optimize the operating conditions in the separation of the total whey proteins from whey by continuous foam fractionation method using response surface methodology (RSM). The effects of the different process variables such as pH (X1) of proteins in feed, gas flow rate, (X2) of initial feed solution, protein: surfactant ratio (X3) and volumetric flow rate (X4) where investigated on the performance criteria of fractionation of raw processed whey. Four factors, three levels Box-Behnken design was used for the optimization procedure. Quadratic model regression equations and response surface plots correlate independent variables (X1, X2, X3 and X4) and dependent variables (response) such as concentration of Foamate (Cf), Enrichment ratio (Er), and percentage Recovery (% Rp) of total whey proteins. All the four factors had significant effects on the response variables. The model predicted that the optimized values of the factors (X1, X2, X3 and X4) such as 5, 290, 1.5 and 14, respectively. The predicted responses were (concentration of foamate, enrichment ratio, and percentage recovery) such as 6647.32, 13.27, and 78.02, respectively. Experiments were performed with the predicted values of factors.

2_4_519_523_800

519-523
Gouri Satpathy, Yogesh Kumar Tyagi, Rajinder Kumar Gupta
DOI 10.5155/eurjchem.2.4.524-534.438

This article describes a simple, quick and inexpensive method for determination of pesticides in fruits and vegetables. The method, known as the quick, easy, cheap, effective, rugged and safe (QuEChERS) method for pesticide residues, involves the extraction and simultaneous liquid-liquid partitioning formed by adding anhydrous magnesium sulfate (MgSO4) plus sodium acetate (NaAc) followed by a simple cleanup step known as dispersive solid-phase extraction (dSPE). The extracts were analyzed by three-dimensional gas chromatography GC/MSD/µ-ECD/FPD in trace ion mode and liquid chromatography/tandem mass spectrometry (LC/MS-MS). Method sensitivity, linearity, repeatability and reproducibility, accuracy, matrix effects, and overall uncertainties have been studied for method validation according to the international norm ISO/IEC: 17025:2005 for both techniques. Identification, quantification and reporting with Total and Extracted ion chromatograms, µECD and DFPD were facilitated to a great extent by Deconvolution Reporting Software (DRS) for GC and Mass hunter software for LC. For all compounds LODs were 0.001 to 0.01 mg/kg and LOQs were 0.005 to 0.020 mg/kg. Correlation coefficients of the calibration curves were >0.991.To validate the effects of matrices, repeatability, reproducibility, recovery and overall uncertainty were calculated for twenty-four matrices at 0.020, 0.050 and 0.500 mg/kg. Recovery ranged between 75-107 % with RSD <17 % for repeatability and intermediate precision and UM of ± 13-22 %.

2_4_524_534_800

524-534
Emad Mahrous Atta, Ahmed Ismail Hashem, Ahmed Morsy Ahmed, Salah Mohamed Elqosy, Marsyl Jaspars, Eman Ramadan El-Sharkaw
DOI 10.5155/eurjchem.2.4.535-538.62

Five main flavonoid glycosides were isolated from the ethanolic extract of Diplotaxis harra (Cruciferae), and were identified as quercetin, isorhamnetin 3-rhamnoside, isorhamnetin 3-o-rutinoside, isorhamnetin 3-glucosyl-4`-rhamnoside and isorhamnetin 3-o-β-glucoside. These compounds were identified according to their Rf values, partial and complete acid hydrolysis, UV, 1H-NMR, 13C-NMR and 2D NMR (HSQC, HMBC) spectroscopy. The alcoholic extract of plant was evaluated against some bacterial strains which showed moderate antibacterial activity, while petroleum ether extract doesn't show any activity.

2_4_535_538_800

535-538
Emtithal Ahmed El-Sawi, Tahia Bayoumy Mostafa, Hyam Ali Radwan
DOI 10.5155/eurjchem.2.4.539-543.55

Isatin-3-imine derivatives (1a-d) have been synthesized. These compounds were then converted into phosphorylated products 2a, 2c with triethylphosphite and 3a-d with triphenylphosphine. The structures of the new compounds were confirmed by elemental analyses, IR, UV/VIS, 1H NMR, 13C NMR and MS studies. The structure of compound 1a was also confirmed by single crystal X-ray diffraction studies. Compounds 1b-d and 3c-d exhibited potent antibacterial activity against Bacillus subtilis and Escherichia Coli. Compound 3a was found to exhibit antifungal activity against the tested organisms.

2_4_539_543_800

539-543
Abdou Osman Abdelhamid, Abdelgawad Ali Fahmi, Abeer Bahlol Ali
DOI 10.5155/eurjchem.2.4.544-551.478

2,3-Dihydro-1,3,4-thiadiazoles, triazolino[4,3-a]pyrimidines, isoxazoles and isoxazolo[3,4-d]pyridazines containing coumarin moities were synthesized from the reactions of methyl (or benzyl) carbodithioate, pyrimidine-2-thione and 3-(3-(dimethylamino)acryloyl)-2H-chromen-2-one derivatives with C-coumarinoyl-N-phenylhydrazonoyl bromide. The structures of all the newly synthesized compounds were confirmed by elemental analyses and spectral data.

2_4_544_551_800

544-551
Wafaa S. Hamama, Hanafi Hassan Zoorob, Osama Abd El-Magid
DOI 10.5155/eurjchem.2.4.552-557.265

Quinuclidin-3-one (1) was used as a versatile intermediate for the synthesis of fused and spiro quinuclidine and its C-nucleosides. The reaction of 1 with formalin and secondary amines namely; morpholine, piperidine, and piperazine afforded the corresponding Mannich bases 2-4 in acid medium. Quinuclidino[3,2-b]pyran 5 has been synthesized via a selective cyclocondensation reaction between Mannich base of quinuclidinone hydrochloride 2 and malononitrile. The transformation of 1 with formalin and methylamine in molar ratio (1:20:2) afforded the spiro compound 7. Ring expansion of 2 under Schmidt reaction conditions gave the 1,3-diazabicyclo[3.2.2]nonanone derivative 6. Eventually, the synthesis of C-nucleosides 10, 12-14 were achieved by using aldohexoses and aldopentose catalyzed by zinc chloride, while, the bis-quinuclidine derivative 15 was obtained by using sodium carbonate. Newly synthesized compounds were characterized by IR, 1H NMR, and mass spectral data.

2_4_552_557_800

552-557

Short Communication

Ramaraj Sivakumar, Ramachanran Vasanthakumari Pradeepchandr, Korlakunta Narasimha Jayaveera
DOI 10.5155/eurjchem.2.4.558-560.275

A series of benzimidazole containing isoxazoline-5-one compounds were computationally designed and optimized with the Hex to investigate the interactions between the target compounds and amino acid residues of the Escherichia coli peptide deformylase (PDF).Ni enzyme. These compounds docked into the active site of peptide deformylase (PDB code, 1G2A) using  Hex docking tools software, which showed good affinity for the enzyme when compared with the binding energies of standard drugs such as amoxicillin (-237.61) and ciprofloxacin (-229.60). Among all the designed compounds, the compound 3 shows more binding energy values (-325.17). Further, we planned to synthesis these benzimidazole derivatives and screen for in-vitro anti-bacterial effect on different microorganisms.

2_4_558_560_800

558-560

Review Article

Faheem Amir, Wan Sinn Yam, Yen Chin Koay
DOI 10.5155/eurjchem.2.4.561-565.455

Erythrina indica commonly known as Coral tree has been widely used in Indian traditional medicine for treating common ailments such as asthma, arthritis, diarrhoea, fever, inflammation and leprosy. Certain phytochemical constituents such as: alkaloids, aliphatic fatty acids, alkaloids have also been reported. A wide range of medicinal formulations have been developed from E. indica that exhibit analgesic, antiarthritic, anti-hypertriglyceridemia, anti-inflammatory and muscle relaxing effects. This review summarizes the phytochemical investigations and pharmacological activities of E. indica.

2_4_561_565_800

561-565


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