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  • Open access
  • 74 Reads
Synthesis and Characterization of Tin(II) 5,10,15,20-Tetrakis(4-Phenylbenzoate)Porphyrin and Tin(II) 5,10,15,20-Tetrakis(4-[1,1ʹ-Biphenyl]-4ylbenzoate)Porphyrin
Porphyrins are stable molecules with a macrocyclic conjugated system and often peripheral substituents. Herein we reported the synthesis and characterization of a new type of metalloporphyrin. SnTCPP was synthesized and dissolved in THF, and then thionylchloride was slowly added into solution to start reaction under stirring at 70 ⁰C for 2 h. The excess thionylcholoride must be removed. Then phenol or 1, 1ʹ-biphenyl – 4– ol was added to the solution and the mixture was stirred and refluxed for 8 h. The corresponding products (5,10,15,20-tetrakis(4-phenylbenzoate)porphyrin and 5,10,15,20-tetrakis(4-[1,1ʹ-biphenyl]-4yl benzoate)porphyrin) were obtained. We identified the products by FT-IR and UV-Vis techniques. We investigated the effect of functional groups (phenol and 1, 1ʹ-biphenyl – 4– ol) in photocatalytic degradation of methylene blue under visible light irradiation in the same conditions.
  • Open access
  • 114 Reads
Structural Modifications on Natural-based Products: Synthetic Strategies and Biological Applications
Coumarins are a class of heterocyclic compounds present in a significant quantity in several plants. The simplest coumarin, a benzene ring fused with a pyran-2-one heterocycle, was first discovered in the 19th century and since then, due to the synthetic accessibility and the biological properties of its derivatives, has been playing an important role in the Medicinal Chemistry field. In fact, coumarins have been previously described as anticancer, antiviral, anti-inflammatory, antimicrobial, enzymatic inhibitory and antioxidant agents.Another two interesting compounds found widely in nature are resveratrol derivatives and chalcones. Both families of compounds are known for having remarkable antioxidant activity, cardio- and neuroprotective effects, among other relevant biological properties. Therefore, we devised several synthetic strategies to incorporate these natural products in one compound, combining their potential as promising agents for the treatment of several illnesses. In our group, we have already synthesised multiple novel compounds incorporating into the coumarin scaffold the resveratrol or chalcones moieties with remarkable activities towards different pharmacological targets. In this work, we continue exploiting this strategy by incorporating different linkers at coumarin position 3, thus giving us a wide range of possibilities for new compounds.
  • Open access
  • 66 Reads
Comparison of Minimal Inhibitory Concentration of Porphyrin Compounds Against Bacillus Subtilis Under Irradiation With Visible Light
In this study, the effect of meso-tetrakis (N-methyl-3-pyridyl)porphyrin (TMPyP(3)), meso-tetrakis (4-N, N, N-trimethylanilinium) porphyrin (TAPP) and their zinc compounds irradiated with visible light, on a Gram positive bacterium, Bacillus subtilis, was investigated and compared. MIC, MBC and inhibition zones produced by these compounds were determined and the bacteria numbers were counted. The results indicate that TAPP and its zinc compound have more effective inhibitory activity than others against this bacterium.
  • Open access
  • 119 Reads
Preparation of Glibenclamide Nanoparticles
One of the progressive ways for increasing oral bioavailability of drug substances with poor solubility is nanoparticles preparation. Glibenclamide (Biopharmaceutical Classification System class II) was chosen as a model compound with low solubility and high permeability. Nanoparticles were prepared either by the antisolvent precipitation – solvent evaporation method or by the emulsion solvent evaporation method. Sodium dodecyl sulphate and macrogol 6000 were used as stabilizing excipients in aqueous solutions with the mass concentrations of 1, 3 and 5%. Acetone and dichloromethane were used as glibenclamide solvents. Ten samples were characterized by dynamic light scattering. The particles size of seven samples ranged from 4.4 to 27.0 nm.
  • Open access
  • 89 Reads
Synthesis of 4H-Pyran Derivatives via a Green One-Pot Multicomponent Reaction Catalyzed by CuFe2O4¬ Magnetic Nanoparticles as a Reusable Catalyst
Recently, environmental pollution and the economic crisis have become very important global challenges. Nowadays, industrial and manufacturing units including chemicals and pharmaceutical companies show propensity to environmentally friendly protocols that is so-called green and sustainable protocols. In this field, green chemistry plays an efficient role. One of the important strategies in green chemistry is multicomponent reactions (MCRs). On the other hand, catalysts are powerful tools to improve reaction conditions. Application of nanoscience in this field leads to a wide range of academic and industrial researches to obtain greenprocedures.2-Amino-4H-pyran derivatives are important molecules because of their biologicalactivities such asantiallergic, antitumor, antibacterial, diuretic, anti-coagulant, and anti-anaphylactic. Also reusability of catalysts is an important challenge in green chemistry. Magnetic nanoparticles (MNPs) are used as efficient catalysts, because they are easily separable and recyclable and have high surface area vs. bulk materials that improves their activity. In continuation of our interest in the application of new catalysts in organic synthesis via MCRs, herein, we represent an environmentally friendly synthesis of 4H-pyrans via a green one-pot threecomponent reaction using MNPs CuFe2O4 as catalyst under mild reaction conditions in good to excellent yields.
  • Open access
  • 77 Reads
Structurally Complexes Aromatic Aldehydes on Knoevenagel Condensation Catalyzed by Chitosan Hydrogel Beads
Nowadays, the synthesis of applicable products in everyday life is an increasing research topic. Knoevenagel condensation presents a broad range of applications in synthesis of multiple substances involving domino reactions to obtain five- and six-membered heterocycles such as polysubstituted pyrrolidines, dihydrothiophenes and 1,4-dihydropyridines. Chitosan has been employed as support of metallic catalysts in hydrogenation of ethyl cinnamate, Suzuki cross coupling or to transform nitriles into amides. Very recently, this polymer has been used in several reactions (e.g. aldol, Henry o Michael reactions) as heterogeneous catalyst using simple aldehydes. We report here, the synthesis of new Knoevenagel switchable products obtained from malononitrile and highly modified aldehydes owning different steric hindrance and electronic effects. The heterogeneous chitosan catalyst role has been studied to improve on conversion, time and yields compared with non-catalyzed reactions.We thank the AECID (Projects A/023577/09 and A/030422/10) and the 'Junta de Andalucía' (FQM 142 and Project P09-AGR-4597) for financial support.
  • Open access
  • 72 Reads
Preparation and Photochemistry of 3-O-Methylestra-1,3,5(10)-Triene-17beta-yl Cinnamates and 3-O-Methylestra-1,3,5(10)-Trien-17-one O-Cinnamoyl-17-Oximes
3-O-Methylestra-1,3,5(10)-triene-17beta-yl (E)-cinnamates and 3-O-methylestra-1,3,5(10)-trien-17-one O-(E)-cinnamoyl-17-oximes were prepared from the reaction of cinnamic acids with 3-O-methylestra-1,3,5(10)-trien-17-beta-ol and 3-O-methylestra-1,3,5(10)-trien-17-one 17-oxime, respectively, in the presence of PPh3-CBrCl3 in an Appel-type reaction. Under photolysis, the steroidal cinnamates underwent E-/Z-isomerisation, while the steroidal O-cinnamoyloximes underwent E-/Z-isomerisation concomitant with cleavage reactions.
  • Open access
  • 167 Reads
Green Synthesis of BaCrO4 Nanoparticles Using Glycyrrhiza Glabra Extract
The 'greener' environmentally friendly processes in chemistry and chemical technology are becoming increasingly popular and are much needed as a result of worldwide problems associated with environmental contamination.  The biosynthesis of nanoparticles has been proposed as a cost effective and environmental friendly alternative to chemical and physical methods. Plant mediated synthesis of nanoparticles is a green chemistry approach that interconnects nanotechnology and plant biotechnology. The techniques for obtaining nanoparticles using naturally occurring reagents such as plant extracts could be considered attractive for nanotechnology. Plant parts such as leaf, root, latex, seed, and stem are being used for nanoparticle synthesis. Overall, biological materials provide an environmentally friendly or greener chemical method to produce invaluable materials because the biomaterial based routes eliminate the need to use harsh or toxic chemicals. Barium chromate is a naturally occurring chromate analogue of barite which is widely used as a model system for morphosynthesis and kinetics crystallization studies as they crystallize only in a single modification. Barium chromate has been extensively studied attributing to their unique properties and potential applications such as oxidation agent, catalyst for enhancing vapor-phase oxidation reaction and excellent photo-physical properties. In the present study, we have reported the green synthesis and characterization of barium chromate nanoparticles using Glycyrrhiza glabra extract as a natural surfactant, which -to the best of our knowledge- is the first report. The formed BaCrO4 NPs were characterized by Ultraviolet-Visible (UV–Vis), Fourier-transform Infrared spectroscopy (FT-IR), X-ray diffraction (XRD) and scanning electron microscopy (SEM) analysis.
  • Open access
  • 84 Reads
Antiproliferative Activity of 2,3,6,7-Tetrahydro-1H-Benzo[a]Quinolizino[1,9-hi]Phenoxazin-14(5H)-Iminium Chloride Derivatives
The julolidine (conventional name for 1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolone)-based compounds have been reported as ligands that can detect Cu2+ by colorimetric and fluorometric methods, and as inhibitors of the amyloid-β protein self-assembly (which is associated the pathogenesis of Alzheimer's disease). Furthermore, the presence of this rigid structure has shown to increase the fluorescence quantum yield comparatively to the respective unrestricted dye. Taking this in account, we decided to explore the influence of the julolidine moiety in the properties of benzophenoxazine derivatives, by evaluating the antimicrobial activity against Saccharomyces cerevisiae PYCC 4072 of newly synthesised fluorescent 2,3,6,7-tetrahydro-1H-benzo[a]quinolizino[1,9-hi]phenoxazin-14(5H)-iminium chlorides, in comparison with their analogues. Thanks are due to the Fundação para a Ciência e Tecnologia (FCT, Portugal) for financial support to the NMR portuguese network (PTNMR, Bruker Avance III 400-Univ. Minho), FCT and FEDER (European Fund for Regional Development)-COMPETE-QREN-EU for financial support to Research Centres CQ/UM [PEst-C/QUI/UI0686/2013 (FCOMP-01-0124-FEDER-037302)] and CBMA (project PEst-OE/BIA/UI4050/2014). Post-doctoral grant to B. R. Raju (SFRH/BPD/62881/2009) is also acknowledged to FCT, POPH-QREN, and FSE.
  • Open access
  • 94 Reads
Determination of Complexation Parameters for β-Cyclodextrin and Randomly Methylated β-Cyclodextrin Inclusion Complexes of p-Cumaric Acid Using Reversed-Phase Liquid Chromatography
p-cumaric acid (PCA) i.e. hydroxycinnamic acid is a one of the major component of lignin. PCA can be found in a wide variety of edible plants including peanuts, beans, tomatoes, carrots, garlic etc. It is also found in wine and vinegar. PCA has strong antioxidant properties and is known to reduce the risk of stomach cancer by reducing the formation of carcinogenic nitrosamines. According to that tha main goal of presente dpaper is to establish the basic properties of PCA complexes with some cyclodextrin. Host-guest complexation with cyclodextrins may be interesting to increase the bioavailability of PCA in functional food product. During the research an on-line complexation of p-cumaric acid  with β-cyclodextrin (CD) and and Randomly Methylated β-cyclodextrin (RMCD) was performed using RP-HPLC system. Due to the complex formation of CD with a guest molecule - PCA a significant changes in retention times of PCA was observed. The investigation was performed as a function of temperature as well as cyclodextrin concentration in liquid phase. As a result apparent formation constant – KF of PCA/CD and PCA/RMCD were calculated. Based on KF some thermodynamic properties were obtained including standard enthalpy, standard entropy and free Gibbs energy of host-guest complexation. It was shown that the stoichiometry of the complex in both cases is 1:1 and the complexation is an exothermic process. From the other hand the positive value of Gibbs free energy clearly designate the process as forced one. The increase in temperature influence on Gibbs free energy by means of increase of this parameter. Additionally the differences between CD and RMCD as a hosting agents were shown.
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