Vol 8, No 1 (2017)

March 2017

Table of Contents


Hakan Arslan
DOI 10.5155/eurjchem.8.1.i-ii.1559
Editorial Board
Hakan Arslan
DOI 10.5155/eurjchem.8.1.iii-vii.1560
Graphical Contents

Research Article

Zarife Sibel Şahin, Mine Yarım, Meriç Köksal
DOI 10.5155/eurjchem.8.1.1-7.1512

The crystal and molecular structure of 1-{3-[4-(4-fluorophenyl)piperazin-1-yl]propyl}-1H-indole (I) has been determined by single-crystal X-ray diffraction. Molecular geometry of compound I in the ground state has been calculated using the density functional method (DFT) with B3LYP/6-31G(d,p) basis set and compared with the experimental data. In addition, density functional calculations of the structure, molecular electrostatic potential map, frontier molecular orbitals, atomic charges, thermodynamic functions and global chemical reactivity descriptors of compound I were performed.

Sherif Abdel-Naby Abdel-Gawad
DOI 10.5155/eurjchem.8.1.8-12.1514

Simple, selective and precise spectrophotometric methods were applied for simultaneous quantification of sofosbuvir (SFV) and ledipasvir (LDI) both in their raw and dosage forms. In the first method, the two cited drugs were determined simultaneously using first derivative (D1) method. It was accomplished by measuring peak heights at 275 nm and 344 nm, for SFV and LDI, respectively, in concentration ranges of 5 - 80 μg/mL and 3 - 50 μg/mL, for SFV and LDI, respectively. In the second one, a first derivative of ratio spectra (1DD) method was adopted to quantify SFV in concentration range of 5 - 80 µg/mL. It was adopted by measuring the peak amplitudes (valley and peak) at 259 nm and 280 nm, using 25 µg/mL LDI as a divisor. The proposed method was also used to determine LDI in concentration range of 3 - 50 µg/mL by recording the peak amplitudes (valley and peak) at 319 nm and 375 nm, using 80 µg/mL SFV as a divisor. The developed methods were validated with respect to linearity, accuracy, precision, selectivity, robustness and limits of detection and quantification (LOD and LOQ), as per the guidelines of International Conference on Harmonization (ICH)-Q2B.

Ming Jun Cen, Yu Wang, Yong Wu He
DOI 10.5155/eurjchem.8.1.13-14.1525

A general method for the synthesis of trans-4-nitrostilbenes has been developed. The trans-4-nitrostilbene could be synthesized in good yields under microwave irradiation within 10 min through Perkin reaction by using 4-nitrophenylacetic acid, benzaldehydes and pyrrolidine.

Sohail Saeed, Naghmana Rashid, Shaaban Kamel Mohamed
DOI 10.5155/eurjchem.8.1.15-17.1521

The biologically active N,N'-di(2-hydroxybenzylidene)hydrazine has been synthesized and specifically characterized by X-ray crystallography. There are two molecules of N,N'-di(2-hydroxybenzylidene)hydrazine, C14H12N2O2, in the unit cell. The N,N'-di(2-hydroxy benzylidene)hydrazine molecule is planar, with maximum deviation from the mean plane being less than 0.028(2) Å. Intramolecular O-H···N hydrogen bonding interactions were observed in the crystal lattice which connected the molecules into chain running along b-axis.

Amel Ferhati, Achene Bouchemma, Mustapha Bouhenguel, Leila Lefrada, Assia Sid
DOI 10.5155/eurjchem.8.1.18-19.1510

A new triazinane derivative was obtained by condensation reaction of pentylamine, 2-fluoroaniline and formaldehyde (formalin) in basic solution to yield 1,3-bis(2-fluorophenyl)-5-pentyl-1,3,5-triazinane. The structure of the synthesized compound was characterized by spectroscopic methods: FT-IR, UV-Vis, 13C, 19F and 1H NMR.

Kazuki Ogata, Atsushi Nagasawa, Noriyuki Yonezawa, Akiko Okamoto
DOI 10.5155/eurjchem.8.1.20-24.1530

Crystal structure of the title compound, 7-methoxy-1-{[(E)-2,6-dimethylphenylimino] (phenyl)methyl}-2-naphthol, which has N-aryl group instead of ketonic carbonyl group has been comparatively analysed with the precursor compound of 1-benzoyl-2-hydroxy-7-methoxynaphthalene. The distinct features in the molecular accumulation structures of title triarylimine compound and the precursor diaryl ketone demonstrate that the spatial organization of the former is mainly determined π-π stacking interaction and for the latter the non-classical hydrogen bondings govern the spatial organization. Besides both of the compounds show non-coplanaryl accumulation of aromatic rings molecular structure, the title compound has molecular core of imino group which attaches three aromatic rings of C-1-naphthyl, C-phenyl, and N-phenyl stems of nearly perpendicular alignment of each aryl groups to residual two aryl ones respectively, giving highly congested circumstance at the inner site of molecules. On the other hand, the precursor aromatic ketone molecule has relatively large space compared to title compound, enabling conformational flexibility to some extent within restriction of maintaining non-coplanar organization. The molecules of the precursor compound in crystal are stabilized by a number of non-covalent bonding interactions, mainly by non-classical hydrogen bondings. The achievement stabilization contributed a number of non-classical hydrogen bonding is considered to be due to the inner-molecular motility of single molecular structure. Contrarily, the congested inner-molecular situation of title compound makes largely rigid molecular conformation, which affords at the same time exposure of three aromatic planes outside the molecular core. The single molecular organization permits π-π stacking interaction stabilization instead of formation of a number of weak interactions. Thus, the governing factors for the distinct feature of the single molecular and the accumulation structures of title compound and the precursor are interpreted from the viewpoint of predominantly effective intermolecular interaction, a strong π-π stacking interaction or sum of weak non-classical hydrogen bondings, determined by the inner-molecular congestive conditions directly affects the inner-molecular motility.

Rohini Narayan Shelke, Dattatraya Navnath Pansare, Chandrakant Dhondiram Pawar, Arun Khandu Deshmukh, Rajendra Pandu Pawar, Saroj Ram Bembalkar
DOI 10.5155/eurjchem.8.1.25-32.1522

Microwave assisted and conventional synthetic methods of new 6-bromo-2-(substituted)-3H-imidazo[4,5-b]pyridine and its derivatives are described, which were obtained in reduced reaction times, higher yields, cleaner reactions than previously described methods. All the synthesized compounds were characterized, and screened for their anticancer and antimicrobial activity. Among synthesized compounds 3b and 3k shows prominent antibacterial activity and compound 3f shows both antibacterial and antifungal activity. Compounds 3h and 3j shows prominent anticancer activity against the both breast cancer cell lines, MCF-7 and BT-474. These results suggest that the imidazo[4,5-b]pyridine moiety may serve as a new promising template for synthesis of anticancer and antimicrobial agents and further study is required for evaluation of their mechanism of action.

Akiko Okamoto, Toyokazu Muto, Siqin Gaowa, Genta Takahara, Noriyuki Yonezawa
DOI 10.5155/eurjchem.8.1.33-41.1529

Crystal structure of 1-(4-hydroxybenzoyl)-2,7-dimethoxynaphthalene, C19O4H16, is reported from the viewpoint of characteristics in the helical alignments and difference compared to the crystal structure of a structural isomeric compound. The asymmetric unit of title compound contains two conformers A and B. Furthermore, the molecules in crystal exhibit atropisomerism brought about by molecular stereogenic axis of carbon-carbon bond between the carbonyl moiety and the naphthalene ring. Therefore, a pair of R- and S-enantiomeric molecules exists for each conformer. The two pairs of the enantiomeric molecules are related by two-fold helical axis in the asymmetric unit of P21/c space group, exhibiting the number of molecules is eight, Z = 8. Single molecular structure of title compound shows non-coplanarly accumulated aromatic-rings structure. The molecular packing structure is mainly stabilized non-classical hydrogen bonds involving C-H…O hydrogen bonds and C-H…π ones, however O-H…O=C classical hydrogen bonds are solely formed between same configured conformers. Comparison with the spatial alignment of an isomeric homologue, 2-hydroxy-1-(4-methoxy benzoyl)-7-methoxynaphthalene, has clarified that substitution position of hydroxy group determines not only direction of classical hydrogen bonds but also total feature of molecular packing, i.e., the homologous compound, which has hydroxy group at 2-position of naphthalene core forms intramolecular O-H…O=C classical hydrogen bond, and O-H…OMe classical hydrogen bonds between opposite enantiomeric isomers. The presence/absence and direction of the predominantly strong classical hydrogen bonds govern balance of interactions of other less effective classical and non-classical hydrogen bonds in molecular packing. In homologous compound, each of non-classical hydrogen bonds between same signed enantiomeric isomers and those between opposite enantiomeric isomers demonstrates almost same distances. In title compound, both types of non-classical hydrogen bonds formed by conformer A are imbalanced. The imbalanced non-classical hydrogen bonds are adjusted and reinforced by non-classical hydrogen bonds between conformers A and B.

Yellanki Jagannadham, Bhoomireddy Ramadevi, Bethanamudi Prasanna
DOI 10.5155/eurjchem.8.1.42-45.1519

The title compounds, substituted 1H-benzo[f]chromen-3-yl-2H-chromen-2-ones were obtained by reacting 3-aryl-1-(3-coumarinyl)propen-1-ones with 2-napthol catalyzed by DBU (1,8-diazabicyclo[5,4,0]undec-7-ene) and concentrated H2SO4 in ample yields. Their structures were characterized by IR, 1H NMR, 13C NMR, mass spectral and elemental analysis. All the synthesized compounds have been evaluated for their in-vitro antibacterial activity against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa and antifungal activity against Aspergillus Niger and Candida albicans by using serial broth dilution method. Among those compounds 3 band 3c exhibits prominent results.

Muhammad Shabbir, Zareen Akhter, Ahmad Raza Ashraf, Michael Bolte, Sumbal Wahid, Bushra Mirza
DOI 10.5155/eurjchem.8.1.46-51.1535

Four ONNO donor Schiff bases 2-((E)-(2-((E)-2-hydroxybenzylideneamino)ethylimino) methyl)phenol (H2L1), 2-((E)-(2-((E)-2-hydroxybenzylideneamino)propylimino)methyl) phenol (H2L2), 2-((E)-1-(2-((E)-1-(2-hydroxyphenyl) ethylideneamino)ethylimino)ethyl) phenol (H2L3) and 2-((E)-1-(2-((E)-1-(2-hydroxyphenyl)ethylideneamino)propylimino) ethyl)phenol (H2L4) were synthesized by the reactions of ethylene/propylene diamines with 2-hydroxy benzaldehyde/2-hydroxy acetophenone. The new compounds were characterized by FT-IR and NMR (1H and 13C) spectroscopic techniques accompanied by elemental, GC/MS and single crystal X-ray diffraction analyses. These compounds were screened for various biological studies i.e. brine shrimp cytotoxic, antitumor and antibacterial activities The compound H2L3 showed highest cytotoxic and antitumor activities with lowest LD50 (14.27) and IC50 values (18.90). All the compounds were highly active in protecting DNA against hydroxyl free radicals. Antibacterial studies had shown that these were inactive against Gram positive bacteria (Staphylococcus aureus and Micrococcus luteus) while active against Gram negative bacteria (Enterobacter aerogenes, Bordetella bronchiseptica and Salmonella typhi) showing variable antibacterial activity.

Mohammed Salem Rizk, Maha Sultan, Dalia Mohamed, Rehab Moussa Tony
DOI 10.5155/eurjchem.8.1.52-59.1523

Simultaneous quantification of levonorgestrel (LEV) and ethinyl estradiol (EE) was performed utilizing five different spectrophotometric methods and a high performance thin layer chromatographic method (HPTLC). The applied spectrophotometric methods were based on either ratio spectra namely; ratio difference, ratio subtraction and derivative ratio or the presence of isosbestic point specifically; absorbance subtraction and amplitude modulation. The proposed methods had the ability to resolve the overlapped spectra of the drugs with a linear relationship in the concentration range 1-65 µg/mL and 1-95 µg/mL for LEV and EE, respectively. The developed HPTLC method has revealed a good separation of the drugs upon utilizing Nano Silica Gel on TLC plates with fluorescent indicator 254 nm glass plates as the stationary phase and chloroform: methanol (99:1, v:v) as the mobile phase. The proposed HPTLC method has shown high sensitivity, where the linearity range was 0.02-3.00 µg/band and 0.5-20.0 µg/band, for LEV and EE, respectively. The proposed methods were successfully applied for the analysis of laboratory prepared mixtures as well as combined dosage form. Validation for all methods was conducted in compliance with the ICH guidelines proving the methods to be selective, linear, precise and accurate. The proposed methods were statistically compared with the pharmacopoeial method, where the obtained results showed no significant difference regarding accuracy and precision.

Sabina Jhaumeer Laulloo, Minu Gupta Bhowon, Matthew Akerman, Nausheen Joondan, Marie Jessika Momus
DOI 10.5155/eurjchem.8.1.60-65.1540

A series of dialkyl 2,2’-disulfanediyldibenzoates with alkyl chain length C8 to C12 were synthesized and characterized by spectral studies. The structure of compound 3 was also confirmed by X-ray crystallography. The compounds were found to possess good antibacterial activity, especially with respect to Gram positive bacteria, and the activity was found to increase with concomitant increase in chain length. Binding studies of compound 3 with the synthetic phospholipid 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) showed that the compound interacts with biological membrane mainly via hydrophobic interactions.

Chenna Krishna Reddy Reddivari, Subba Rao Devineni, Jyothi Kumar Malaka Venkateshwarulu, Vijaya Bhaskar Baki, Appa Rao Chippada, Rajendra Wudayagiri, Rami Reddy Yallala Venkata, Naga Raju Chamarthi
DOI 10.5155/eurjchem.8.1.66-75.1515

A series of 5-substituted and 1,5-disubstituted tetrazoles were synthesized in high yields from various biologically active substituted nitriles with sodium azide under heterogeneous catalysed (ZnBr2-SiO2) [2+3] cycloaddition conditions. This reaction gave an excellent yield in the presence of catalytic amount of 0.2 g of ZnBr2-SiO2, glycerol solvent system under microwave irradiation conditions. All the prepared compounds were characterized by elemental analysis 1H NMR, 13C NMR, FT-IR, and mass spectral data. The newly synthesized compounds were investigated for their respective molecular target using molecular docking studies. The results reveal that compounds 5a, 5c, 5e and 3e have conferred with multi target property. The compounds 5a, 5c and 5e have shown the highest binding affinities of -10.1, -9.7 and -10.6 with reverse transcriptase, -8.5, -8.2 and -8.9 with Aurora B, respectively. The compounds 5a, 5e and 3e have shown -8.9, -8.5 and 8.4 with Aromatase, respectively. In addition, the antioxidant activity data reveals that all the compounds showed good antioxidant activity, particularly the compounds 3d, 5d, and 5e exhibited promising radical scavenging activity.

Yousry Ahmed Ammar, Samir Youssef Abbas, Marwa Ahmed Mohamed Shehab El-Sharief, Mohamed Abd El-Rashid Salem, Ahmed Ragab Mohamed
DOI 10.5155/eurjchem.8.1.76-81.1542

A series of new imidazolidineiminothiones (2-4) and bis-imidazolidineiminothiones (5) were synthesized through the cycloaddition reaction of N-arylcyanothioformamides (1) with some electrophilic reagents. Structure of imidazolidineiminothione derivatives were established based on spectroscopic IR, 1H NMR, 13C NMR, MS and elemental analyses data. These compounds were screened for their antibacterial and antifungal activities. Among the synthesized compounds, imidazolidineiminothione derivative 3a showed about 25% less potent effect than Ampicillin against S. epidermidis and B. subtilis (MIC, 0.49 μg/mL) and about 50 % less potent effect than Amphotericin B against A. clavatus and G. Candidum. Bis-imidazolidineiminothione derivative 5a was equipotent to the Gentamycin in inhibiting the growth of N. gonorrhoeae (MIC, 0.49 μg/mL), and displayed 50% less active than Amphotericin B against A. clavatus.

Leila Lefrada, Randolf Köhn, Souhila Malki, Wissam Mazouz, Ahcene Bouchemma, Meriem Hadjem
DOI 10.5155/eurjchem.8.1.82-84.1537

This work describes the synthesis, structural characterization and antibacterial activities of 1,3,5-triazacyclohexane type of new compound 1,3-bis-butyl-5-(4-iodophenyl)-1,3,5-triazacyclohexane. The new triazacyclohexanes (R3TAC) with mixed aryl and alkyl N-substituents are synthesized by the reaction of a 1:2 mixture of 4-iodoaniline and n-butylamine with formalin. The synthesized compounds were characterized by spectral analysis IR, 1H NMR and 13C NMR. The compound was screened for it’s antibacterial activity against Gram-positive and Gram-negative bacteria by the diffusion method on agar medium.

Manara Ahmed Ayoub, Eman Hamed Abd-Elnasser, Mona Abdel-Aziz Ahmed, Marium Girgis Rizk
DOI 10.5155/eurjchem.8.1.85-95.1513

Syntheses and physicochemical studies of Mn(II), Co(II), Ni(II) and Cu(II) complexes with tridentate Schiff base ligand (E)-2-((1-(thiophen-2-yl)ethylidene)amino)phenol (HL)(ATS) were characterized by elemental analysis, FT-IR, Mass, 1H NMR, UV-Vis, magnetic moment, thermal analysis (TG and DTG) techniques, molar conductance and fluorescence spectra. The IR spectra showed that complexes were coordinated in metal ions via the imine N, O and S atoms. Magnetic and UV-Vis spectra, indicated that the geometrical structure of Mn(II), Co(II) and Ni(II) complexes are an octahedral while Cu(II) is a tetrahedral. The kinetic thermodynamic parameters such as E*, DH*, DS* and DG* were determined for each thermal degradation stage of TG curves of the metal(II) complexes using Coat-Redfern method. Fluorescence studies indicated that the Schiff base ligand HL(ATS), and its metal(II) complexes can serve as potential photoactive materials as indicated from their characteristic fluorescence properties and study the effect of solvent and pH on it. The catalytic activities of metal(II) complexes were studied using H2O2 solution.

Mahmoud Al-Refai, Mohammad Ibrahim, Abdullah Al-Fawwaz, Armin Geyer
DOI 10.5155/eurjchem.8.1.96-100.1543

A series of 3,4-dihydropyrimidine-2(1H)-thiones (3a-i) were synthesized in moderate yields via a one-pot reaction of 3-acetyl-2,5-diclorothiophene (1), aryl aldehydes (2a-i) and thiourea in methanolic solution of potassium hydroxide under reflux conditions. All newly synthesized compounds were characterized by extensive NMR analysis, including 1D NMR experiments (1H and 13C) and 2D NMR experiments (COSY, HMBC and HSQC), as well as ESI-MS and HRESI-MS data. The antimicrobial activity of all new compounds (3a-f) was tested against bacteria and fungi. Thione derivative (3c) only showed activity against Staphylococcus aureus, Bacillus subtilis and Aspergillus niger.