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Molecules, Volume 14, Issue 5 (May 2009), Pages 1652-1965

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Open AccessArticle A Simple and Efficient Route for Preparing 2,3,5,6-Tetraaminopyridine Hydrochloride Salt
Molecules 2009, 14(5), 1652-1659; doi:10.3390/molecules14051652
Received: 25 March 2009 / Revised: 10 April 2009 / Accepted: 15 April 2009 / Published: 27 April 2009
Cited by 1 | PDF Full-text (225 KB)
Abstract
A simple and efficient route for preparing 2,3,5,6-tetraaminopyridine hydrochloride salt (TAP·3HCl·H2O) was introduced in this paper. The title compound was synthesized, as usual, in two steps (nitration and hydrogenation) with a total yield of 90%. The use of an oleum and
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A simple and efficient route for preparing 2,3,5,6-tetraaminopyridine hydrochloride salt (TAP·3HCl·H2O) was introduced in this paper. The title compound was synthesized, as usual, in two steps (nitration and hydrogenation) with a total yield of 90%. The use of an oleum and fuming nitric acid mixture in the nitration step improved the yield and purity of the intermediate product. A highly efficient hydrogenation using a H2/Pd/C/C2H5OH system was developed. The products were characterized by TG, IR, 1H-NMR, 13C-NMR, HPLC and elemental analysis. Full article
Open AccessArticle On Two Novel Parameters for Validation of Predictive QSAR Models
Molecules 2009, 14(5), 1660-1701; doi:10.3390/molecules14051660
Received: 16 April 2009 / Accepted: 28 April 2009 / Published: 29 April 2009
Cited by 262 | PDF Full-text (235 KB) | Correction | Supplementary Files
Abstract
Validation is a crucial aspect of quantitative structure–activity relationship (QSAR) modeling. The present paper shows that traditionally used validation parameters (leave-one-out Q2 for internal validation and predictive R2 for external validation) may be supplemented with two novel parameters rm2
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Validation is a crucial aspect of quantitative structure–activity relationship (QSAR) modeling. The present paper shows that traditionally used validation parameters (leave-one-out Q2 for internal validation and predictive R2 for external validation) may be supplemented with two novel parameters rm2 and Rp2 for a stricter test of validation. The parameter rm2(overall) penalizes a model for large differences between observed and predicted values of the compounds of the whole set (considering both training and test sets) while the parameter Rp2 penalizes model R2 for large differences between determination coefficient of nonrandom model and square of mean correlation coefficient of random models in case of a randomization test. Two other variants of rm2 parameter, rm2(LOO) and rm2(test), penalize a model more strictly than Q2 and R2pred respectively. Three different data sets of moderate to large size have been used to develop multiple models in order to indicate the suitability of the novel parameters in QSAR studies. The results show that in many cases the developed models could satisfy the requirements of conventional parameters (Q2 and R2pred) but fail to achieve the required values for the novel parameters rm2 and Rp2. Moreover, these parameters also help in identifying the best models from among a set of comparable models. Thus, a test for these two parameters is suggested to be a more stringent requirement than the traditional validation parameters to decide acceptability of a predictive QSAR model, especially when a regulatory decision is involved. Full article
(This article belongs to the Special Issue Molecular Diversity Feature Papers)
Open AccessArticle Chemical Compositions and Antibacterial Activities of the Essential Oils from Aerial Parts and Corollas of Origanum acutidens (Hand.-Mazz.) Ietswaart, an Endemic Species to Turkey
Molecules 2009, 14(5), 1702-1712; doi:10.3390/molecules14051702
Received: 10 February 2009 / Revised: 23 April 2009 / Accepted: 24 April 2009 / Published: 30 April 2009
Cited by 17 | PDF Full-text (140 KB)
Abstract
Essential oils extracted by hydrodistillation from the aerial parts and corollas of Origanum acutidens (Hand.-Mazz.) Ietswaart, an endemic Turkish flora species, were analyzed by GC-MS. The amounts of essential oil obtained from the aerial parts and the corollas were 0.73% and 0.93%, respectively.
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Essential oils extracted by hydrodistillation from the aerial parts and corollas of Origanum acutidens (Hand.-Mazz.) Ietswaart, an endemic Turkish flora species, were analyzed by GC-MS. The amounts of essential oil obtained from the aerial parts and the corollas were 0.73% and 0.93%, respectively. Twenty-five components in both the aerial parts oil and the corolla oil, representing 95.11% and 93.88%, respectively, were identified. The aerial parts and corolla oils were characterized by the predominance of two components: p-cymene (9.43% and 17.51%) and carvacrol (67.51% and 52.33%), respectively. The essential oils were also evaluated for their antimicrobial activity against ten bacteria by the disc diffusion assay. Our findings showed the following order in the sensitivity to the essential oils, as indicated by the corresponding inhibition zones: Proteus vulgaris > Salmonella typhimurium > Enterobacter cloacae > Klebsiella pneumonia > Escherichia coli > Serratia marcescens > Pseudomonas aeruginosa for the aerial parts essential oil, and Salmonella typhimurium > Proteus vulgaris > Enterobacter cloacae > Escherichia coli > Klebsiella pneumoniae > Serratia marcescens > Pseudomonas aeruginosa for the corolla essential oil. The studied essential oils thus exhibited a broad-spectrum of activity against both Gram-positive and Gram-negative bacteria, whereas the tested Gram-positive bacteria were more susceptible to the essential oil samples. Full article
Open AccessArticle Cytotoxic Components of Pereskia bleo (Kunth) DC. (Cactaceae) Leaves
Molecules 2009, 14(5), 1713-1724; doi:10.3390/molecules14051713
Received: 17 March 2009 / Revised: 7 April 2009 / Accepted: 4 May 2009 / Published: 6 May 2009
Cited by 54 | PDF Full-text (122 KB)
Abstract
Dihydroactinidiolide (1) and a mixture of sterols [campesterol (2), stigmasterol (3) and β-sitosterol (4)], together with the previously isolated individual compounds β-sitosterol (4), 2,4-di-tert-butylphenol (5), α-tocopherol (6), phytol (7) were isolated from the active ethyl acetate fraction of Pereskia bleo (Kunth) DC. (Cactaceae)
[...] Read more.
Dihydroactinidiolide (1) and a mixture of sterols [campesterol (2), stigmasterol (3) and β-sitosterol (4)], together with the previously isolated individual compounds β-sitosterol (4), 2,4-di-tert-butylphenol (5), α-tocopherol (6), phytol (7) were isolated from the active ethyl acetate fraction of Pereskia bleo (Kunth) DC. (Cactaceae) leaves. Cytotoxic activities of the above mentioned compounds against five human carcinoma cell lines, namely the human nasopharyngeal epidermoid carcinoma cell line (KB), human cervical carcinoma cell line (CasKi), human colon carcinoma cell line (HCT 116), human hormone-dependent breast carcinoma cell line (MCF7) and human lung carcinoma cell line (A549); and non-cancer human fibroblast cell line (MRC-5) were investigated. Compound 5 possessed very remarkable cytotoxic activity against KB cells, with an IC50 value of 0.81µg/mL. This is the first report on the cytotoxic activities of the compounds isolated from Pereskia bleo. Full article
Open AccessArticle Synthesis, Characterization, Crystal Structure and Antibacterial Activities of Transition Metal(II) Complexes of the Schiff Base 2-[(4-Methylphenylimino)methyl]-6-methoxyphenol
Molecules 2009, 14(5), 1747-1754; doi:10.3390/molecules14051747
Received: 3 April 2009 / Revised: 19 April 2009 / Accepted: 30 April 2009 / Published: 7 May 2009
Cited by 30 | PDF Full-text (242 KB)
Abstract
Five transition metal(II) complexes, [ML2Cl2] 1~5, were synthesized from the reaction of MCl2·nH2O (M = Mn, Co, Ni, Cu, Cd) and the Schiff base ligand 2-[(4-methylphenylimino)methyl]-6-methoxyphenol (C15H15NO2, L), obtained
[...] Read more.
Five transition metal(II) complexes, [ML2Cl2] 1~5, were synthesized from the reaction of MCl2·nH2O (M = Mn, Co, Ni, Cu, Cd) and the Schiff base ligand 2-[(4-methylphenylimino)methyl]-6-methoxyphenol (C15H15NO2, L), obtained by condensation of o-vanillin (2-hydroxy-3-methoxybenzaldehyde) with p-toluidine. They were characterized by elemental analysis, molar conductance, FT-IR spectra, thermal analysis. The structure of complex 1 was determined by single-crystal X-ray diffraction. Its crystal structure is of monoclinic system, space group P21/c with a = 9.0111(18) Å, b = 11.222(2) Å, c =28.130 (6) Å, α = 90 º, β = 92.29(3) º, γ = 90 º, V = 2867.6(10) Å3, Z = 4. The Mn atom is six-coordinate and displays distorted octahedral geometry.The Schiff base ligand and its complexes have been tested in vitro to evaluate their antibacterial activity against bacteria, viz., Escherichia coli, Staphylococcus aureus and Bacillus subtilis. It has been found that the complexes have higher activity than the corresponding free Schiff base ligand against the same bacteria. Full article
Open AccessArticle The Reaction of Diethyl Bromomalonate with p-tert-Butylthia-calix[4]arene: An Approach to Asymmetrical Derivatives
Molecules 2009, 14(5), 1755-1761; doi:10.3390/molecules14051755
Received: 7 April 2009 / Revised: 20 April 2009 / Accepted: 6 May 2009 / Published: 7 May 2009
Cited by 3 | PDF Full-text (86 KB) | Correction | Supplementary Files
Abstract
New dissymmetric and asymmetric p-tert-butylthiacalix[4]arene derivatives were prepared as a result of the reaction of p-tert-butylthiacalix[4]arene with diethyl bromomalonate in the presence of different alkali metals (Cs, K and Na) in refluxing acetone for 7 days. The
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New dissymmetric and asymmetric p-tert-butylthiacalix[4]arene derivatives were prepared as a result of the reaction of p-tert-butylthiacalix[4]arene with diethyl bromomalonate in the presence of different alkali metals (Cs, K and Na) in refluxing acetone for 7 days. The structures of the prepared compounds were investigated by IR, 1H-NMR and MALDI-TOF mass spectroscopy. Full article
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Open AccessCommunication Synthesis of Hydroxytyrosyl Alkyl Ethers from Olive Oil Waste Waters
Molecules 2009, 14(5), 1762-1772; doi:10.3390/molecules14051762
Received: 24 April 2009 / Revised: 6 May 2009 / Accepted: 8 May 2009 / Published: 11 May 2009
Cited by 40 | PDF Full-text (132 KB)
Abstract
The preparation of a new type of derivatives of the naturally occurring antioxidant hydroxytyrosol is reported. Hydroxytyrosyl alkyl ethers were obtained in high yield by a three-step procedure starting from hydroxytyrosol isolated from olive oil waste waters. Preliminary results obtained by the Rancimat
[...] Read more.
The preparation of a new type of derivatives of the naturally occurring antioxidant hydroxytyrosol is reported. Hydroxytyrosyl alkyl ethers were obtained in high yield by a three-step procedure starting from hydroxytyrosol isolated from olive oil waste waters. Preliminary results obtained by the Rancimat method have shown that these derivatives retain the high protective capacity of free hydroxytyrosol. Full article
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Open AccessCommunication Antibacterial Activity of Methyl Gallate Isolated from Galla Rhois or Carvacrol Combined with Nalidixic Acid Against Nalidixic Acid Resistant Bacteria
Molecules 2009, 14(5), 1773-1780; doi:10.3390/molecules14051773
Received: 17 March 2009 / Revised: 4 May 2009 / Accepted: 6 May 2009 / Published: 11 May 2009
Cited by 39 | PDF Full-text (221 KB)
Abstract
Methyl gallate is a major component of Galla Rhois, as carvacrol is of oregano essential oils. Both have shown good antibacterial activity against intestinal bacteria. This study investigated the antibacterial activities of nalidixic acid in combination with methyl gallate and carvacrol against
[...] Read more.
Methyl gallate is a major component of Galla Rhois, as carvacrol is of oregano essential oils. Both have shown good antibacterial activity against intestinal bacteria. This study investigated the antibacterial activities of nalidixic acid in combination with methyl gallate and carvacrol against nalidixic acid resistant bacteria. The combined effect of nalidixic acid with methyl gallate and carvacrol was evaluated using the checkerboard method to obtain a fractional inhibitory concentration index. The results showed that the combinations of nalidixic acid + methyl gallate/carvacrol improved nalidixic acid resistant pathogenic bacteria inhibition with synergy or partial synergy activity. Thus, a strong bactericidal effect of the drug combinations was observed. In vitro data thus suggested that nalidixic acid combined with methyl gallate and carvacrol may be microbiologically beneficial, rather than antagonists. Full article
Open AccessArticle Non-Equilibrium Thermodynamic Analysis of Transport Properties in the Nanofiltration of Ionic Liquid-Water Solutions
Molecules 2009, 14(5), 1781-1788; doi:10.3390/molecules14051781
Received: 1 April 2009 / Revised: 18 April 2009 / Accepted: 27 April 2009 / Published: 11 May 2009
Cited by 7 | PDF Full-text (241 KB)
Abstract
Thenanofiltration of aqueous solutions of the ionic liquids (ILs) 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF4), and 1-butyl-3-methylimidazolium bromide ([Bmim]Br) with a polyamide nanofiltration membrane was investigated. The practical transport coefficients, including hydrodynamic permeability (Lp), reflection (σ) and solute permeability
[...] Read more.
Thenanofiltration of aqueous solutions of the ionic liquids (ILs) 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF4), and 1-butyl-3-methylimidazolium bromide ([Bmim]Br) with a polyamide nanofiltration membrane was investigated. The practical transport coefficients, including hydrodynamic permeability (Lp), reflection (σ) and solute permeability (ω) were calculated in terms of a non-equilibrium thermodynamics approach. It was found that Lp and σ diminished as the concentration of the IL solutions increased. These characteristics are similar to those observed in inorganic electrolyte-water systems. In addition, it was shown that the rejection and volume flux for both ionic liquid solutions rose with feed pressure, while it decreased with feed concentration. The maximum rejection efficiencies for [Bmim]Br and [Bmim]BF4 are 67 % and 60 %, respectively, on our experimental scale. All the data suggests that a highly efficient process for IL separation could be developed when the operating conditions are optimized further. Full article
(This article belongs to the Special Issue Ionic Liquids)
Open AccessArticle Isolation and Immunomodulatory Effect of Homoisoflavones and Flavones from Agave sisalana Perrine ex Engelm.
Molecules 2009, 14(5), 1789-1795; doi:10.3390/molecules14051789
Received: 2 April 2009 / Revised: 29 April 2009 / Accepted: 30 April 2009 / Published: 12 May 2009
Cited by 22 | PDF Full-text (104 KB)
Abstract
Three known flavones and seven known homoisoflavonoids were isolated from the methanolic extract of the leaves of Agave sisalanaPerrine ex Engelm. Their structures were elucidated on the basis of spectroscopic analysis. The isolated compounds were also evaluated for immunopharmacological activity. PBMC were
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Three known flavones and seven known homoisoflavonoids were isolated from the methanolic extract of the leaves of Agave sisalanaPerrine ex Engelm. Their structures were elucidated on the basis of spectroscopic analysis. The isolated compounds were also evaluated for immunopharmacological activity. PBMC were used as target cells, and cell proliferation was determined by 3H-thymidine uptake. (±)-3,9-Dihydroeucomin (4), dihydrobonducellin (5), and 5,7-dihydroxy-3-(4′-hydroxybenzyl)-4-chromanone (7) showed inhibitory effects on PBMC proliferation activated by PHA with IC50 values 19.4, 73.8, and 58.8 µM, respectively. All three compounds significantly inhibited the production of IL-2 and IFN-γ in activated PBMC in a concentration-dependent manner. Full article
Open AccessArticle Effects of a Thiosemicarbazide Camphene Derivative on Trichophyton mentagrophytes
Molecules 2009, 14(5), 1796-1807; doi:10.3390/molecules14051796
Received: 24 March 2009 / Revised: 6 May 2009 / Accepted: 7 May 2009 / Published: 13 May 2009
Cited by 17 | PDF Full-text (1164 KB)
Abstract
Thiosemicarbazides are compounds known for their biological activity, particularly their antimicrobial properties, which include activity against fungi. The difficulty of treating fungal diseases induced us to assess the antifungal properties of some novel thiosemicarbazide compounds. We selected the natural products limonene and camphene
[...] Read more.
Thiosemicarbazides are compounds known for their biological activity, particularly their antimicrobial properties, which include activity against fungi. The difficulty of treating fungal diseases induced us to assess the antifungal properties of some novel thiosemicarbazide compounds. We selected the natural products limonene and camphene as sources for the preparation of these new thiosemicarbazide derivatives. The compound N(4)-[2,2-dimethyl-3-methylnorbornane]-thiosemicarbazide (TIO C) showed an antifungal effect on Trichophyton mentagrophytes, with values of MIC = 55 mmol L-1 and MFC = 110 mmol L-1. Scanning-electron microscopy showed a decrease in mycelium development and morphological alterations of T. mentagrophytes cultured on nail fragments and treated with TIO C. In an attempt to discover its mode of action, we noted that ergosterol is apparently not a target of TIO C activity. An effect of TIO C on T. mentagrophytes cell walls and dividing cross-walls was shown by observed impairment of the fluorescence of tissues stained with calcofluor white, a specific marker for fungal chitin, suggesting that the compound can affect and damage the cell-wall structure or may interfere with its formation, during cell division, growth, and morphogenesis. This approach to the synthesis of new derivatives might provide interesting compounds with greater biological activity in pharmacological research. Full article
Open AccessArticle Antimicrobial Activity of Six Pomegranate (Punica granatum L.) Varieties and Their Relation to Some of Their Pomological and Phytonutrient Characteristics
Molecules 2009, 14(5), 1808-1817; doi:10.3390/molecules14051808
Received: 26 March 2009 / Revised: 29 April 2009 / Accepted: 11 May 2009 / Published: 13 May 2009
Cited by 46 | PDF Full-text (110 KB)
Abstract
Arils from six pomegranate (Punica granatum L.) varieties grown in the Mediterranean region of Turkey were tested for their antimicrobial properties by the agar diffusion and minimum inhibitory concentration (MIC) methods against seven bacteria: (Bacillus megaterium DSM 32, Pseudomonas aeruginosa DSM
[...] Read more.
Arils from six pomegranate (Punica granatum L.) varieties grown in the Mediterranean region of Turkey were tested for their antimicrobial properties by the agar diffusion and minimum inhibitory concentration (MIC) methods against seven bacteria: (Bacillus megaterium DSM 32, Pseudomonas aeruginosa DSM 9027, Staphylococcus aureus Cowan 1, Corynebacterium xerosis UC 9165, Escherichia coli DM, Enterococcus faecalis A10, Micrococcus luteus LA 2971), and threefungi (Kluvyeromyces marxianus A230, Rhodotorula rubra MC12, Candida albicans ATCC 1023). It has been observed that the pomegranate aril extracts had antimicrobial effect on all microorganisms, giving inhibition zones ranging in size from 13 to 26 mm. The MIC values for active pomegranate extracts ranged between 30 and >90 µg/mL. The results obtained appeared to confirm the antimicrobial potential of the Punica granatum varieties. Full article
Open AccessArticle Phenoxypropylamines: Synthesis and Antiulcer Evaluation
Molecules 2009, 14(5), 1818-1824; doi:10.3390/molecules14051818
Received: 9 April 2009 / Accepted: 8 May 2009 / Published: 13 May 2009
PDF Full-text (300 KB) | HTML Full-text | XML Full-text
Abstract
We have synthesized a number of phenoxypropylamines from N-{3-[3-(1-piperidinylmethyl)phenoxy]propyl}chloroacetamide (3). All the products have been characterized by elemental analysis, 1H-NMR and MS. The biological activity effects of the title compounds were examined. From the biological activity results, we found that two
[...] Read more.
We have synthesized a number of phenoxypropylamines from N-{3-[3-(1-piperidinylmethyl)phenoxy]propyl}chloroacetamide (3). All the products have been characterized by elemental analysis, 1H-NMR and MS. The biological activity effects of the title compounds were examined. From the biological activity results, we found that two of themshowed significant gastric acid antisecretory activity. Full article
Open AccessArticle Phytohormones as Important Biologically Active Molecules – Their Simple Simultaneous Detection
Molecules 2009, 14(5), 1825-1839; doi:10.3390/molecules14051825
Received: 7 March 2009 / Revised: 8 May 2009 / Accepted: 14 May 2009 / Published: 15 May 2009
Cited by 8 | PDF Full-text (831 KB)
Abstract
Phytohormones, their functions, synthesis and effects, are of great interest. To study them in plant tissues accurate and sensitive methods are required. In the present study we aimed at optimizing experimental conditions to separate and determine not only plant hormones but also their
[...] Read more.
Phytohormones, their functions, synthesis and effects, are of great interest. To study them in plant tissues accurate and sensitive methods are required. In the present study we aimed at optimizing experimental conditions to separate and determine not only plant hormones but also their metabolites, by liquid chromatography coupled with a UV-VIS detector. The mixture we analyzed was composed of benzyladenine, kinetin, trans-zeatin, cis-zeatin, dihydrozeatin, meta-topolin, ortho-topolin, α-naphthalene acetic acid, indole-3-acetic acid, trans-zeatin-7-glucoside, trans-zeatin-O-glucoside, trans-zeatin-9-riboside, meta-topolin-9-riboside and ortho-topolin-9-riboside. We measured the calibration dependences and estimated limits of detection and quantification under the optimal chromatographic conditions (column: Polaris C18; mobile phase: gradient starting at 2:98 (methanol:0.001% TFA) and was increasing to 55:45 during twenty minutes, and then decreasing for 10 min to 35:65, flow rate: 200 µL·min-1, temperature: 50 °C, wavelength: 210 nm). The detection limits for the target molecules were estimated as tens of ng per mL. We also studied the effect of flax extracts on the phytohormones’ signals. Recovery of aliphatic and aromatic cytokinins, metabolites of cytokinins and auxinswere within the range from 87 to 105 %. The experimental conditions were tested on a mass selective detector. In addition we analysed a commercial product used for stimulation of roots formation in cuttings of poorly rooting plants. The determined content of α-naphthalene acetic acid was in good agreement with that declared by the manufacturer. Full article
Open AccessArticle Synthesis and Properties of Acyclic Ammonium-based Ionic Liquids with Allyl Substituents as Electrolytes
Molecules 2009, 14(5), 1840-1851; doi:10.3390/molecules14051840
Received: 18 April 2009 / Revised: 12 May 2009 / Accepted: 13 May 2009 / Published: 15 May 2009
Cited by 11 | PDF Full-text (177 KB)
Abstract
Several new acyclic ammonium-TFSI ionic liquids with an allyl substituent(s) were synthesized and their physicochemical and electrochemical properties were characterized. [AAMM]Am-TFSI (3) with two allyl groups showed the widest electrochemical stability window (5.9 V) among the ammonium-based ILs reported to date because of
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Several new acyclic ammonium-TFSI ionic liquids with an allyl substituent(s) were synthesized and their physicochemical and electrochemical properties were characterized. [AAMM]Am-TFSI (3) with two allyl groups showed the widest electrochemical stability window (5.9 V) among the ammonium-based ILs reported to date because of the increment of both the anodic and cathodic limits. The charge-discharge performance of a LiCoO2-based half-cell containing [AAMM]Am-TFSI as an electrolyte was better in cycleability (the capacity retention ratio: 99% after 20 cycles) than that of the cell with the corresponding partially saturated analogue, [AMMP]Am-TFSI (2) (the capacity retention ratio: 92% after 20 cycles). Full article
(This article belongs to the Special Issue Ionic Liquids)
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Open AccessArticle Alkylation of 2,4-(1H,3H)-Quinazolinediones with Dialkyl Carbonates Under Microwave Irradiations
Molecules 2009, 14(5), 1860-1868; doi:10.3390/molecules14051860
Received: 16 March 2009 / Revised: 6 April 2009 / Accepted: 9 April 2009 / Published: 20 May 2009
Cited by 11 | PDF Full-text (199 KB)
Abstract
Alkylation is a very important chemical reaction which modifies the biological properties of drugs. Quinazolinedione derivatives are of considerable interest due to their wide array of pharmacological properties.We now report application of a practical alkylation procedure to several quinazolinediones, including pelanserine (5f), which
[...] Read more.
Alkylation is a very important chemical reaction which modifies the biological properties of drugs. Quinazolinedione derivatives are of considerable interest due to their wide array of pharmacological properties.We now report application of a practical alkylation procedure to several quinazolinediones, including pelanserine (5f), which shows antihypertensive properties, 1-methyl-3-(2'-phenylethyl)-1H,3H-quinazoline-2,4-dione (1ab) and 1-methyl-3-[2'-(4'-methoxyphenyl)ethyl]-lH,3H-quinazoline-2,4-dione (1ae), which had been isolated from natural sources. The alkylation was optimized using dimethyl and diethyl carbonates under microwave irradiations. Full article
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Open AccessArticle Modeling the LPS Neutralization Activity of Anti-Endotoxins
Molecules 2009, 14(5), 1869-1888; doi:10.3390/molecules14051869
Received: 6 January 2009 / Revised: 15 May 2009 / Accepted: 19 May 2009 / Published: 20 May 2009
Cited by 23 | PDF Full-text (371 KB)
Abstract
Bacterial lipopolysaccharides (LPS), also known as endotoxins, are major structural components of the outer membrane of Gram-negative bacteria that serve as a barrier and protective shield between them and their surrounding environment. LPS is considered to be a major virulence factor as it
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Bacterial lipopolysaccharides (LPS), also known as endotoxins, are major structural components of the outer membrane of Gram-negative bacteria that serve as a barrier and protective shield between them and their surrounding environment. LPS is considered to be a major virulence factor as it strongly stimulates the secretion of pro-inflammatory cytokines which mediate the host immune response and culminating in septic shock. Quantitative structure-activity relationship studies of the LPS neutralization activities of anti-endotoxins were performed using charge and quantum chemical descriptors. Artificial neural network implementing the back-propagation algorithm was selected for the multivariate analysis. The predicted activities from leave-one-out cross-validation were well correlated with the experimental values as observed from the correlation coefficient and root mean square error of 0.930 and 0.162, respectively. Similarly, the external testing set also yielded good predictivity with correlation coefficient and root mean square error of 0.983 and 0.130. The model holds great potential for the rational design of novel and robust compounds with enhanced neutralization activity. Full article
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Open AccessArticle Sesquiterpenes from Laurencia similis
Molecules 2009, 14(5), 1889-1897; doi:10.3390/molecules14051889
Received: 17 March 2009 / Revised: 21 April 2009 / Accepted: 27 April 2009 / Published: 20 May 2009
Cited by 12 | PDF Full-text (194 KB)
Abstract
One new sesquiterpene, (4E)-1-bromo-5-[(1'S*,3'R*)-3'-bromo-2',2'-dimethyl-6'-methylenecyclohexyl]-3-methylpent-4-ene-2,3-diol (1), and fifteen known sesquiterpenes, isopalisol (2), luzonensol (3), palisadin B (4), aplysistatin (5), palisadin A (6), 4-hydroxyl-palisudin C (7), 5-acetoxypalisadin B (8), 10-hydroxyaristolan-9-one (9), aristol-8-en-1-one (10), aristolan-9-en-1-one (11), aristolan-1(10)-en-9-one (12), aristolan-1(10)-en-9-ol (13),
[...] Read more.
One new sesquiterpene, (4E)-1-bromo-5-[(1'S*,3'R*)-3'-bromo-2',2'-dimethyl-6'-methylenecyclohexyl]-3-methylpent-4-ene-2,3-diol (1), and fifteen known sesquiterpenes, isopalisol (2), luzonensol (3), palisadin B (4), aplysistatin (5), palisadin A (6), 4-hydroxyl-palisudin C (7), 5-acetoxypalisadin B (8), 10-hydroxyaristolan-9-one (9), aristol-8-en-1-one (10), aristolan-9-en-1-one (11), aristolan-1(10)-en-9-one (12), aristolan-1(10)-en-9-ol (13), aristolan-1(10),8-diene (14), aristolan-1,9-diene (15) and aristofone (16), were isolated from a sample of marine red alga Laurencia similis. Their structures were established by detailed NMR spectroscopic analysis and comparison with literature data. Compounds 2-9, and 16 were isolated for the first time from this species. All these metabolites were submitted for a cytotoxicity assay against the tumor cell line BEL7402 (human liver adenocarcinoma), but all of them were found inactive (IC50 > 10 μg/mL). Full article
Open AccessCommunication Synthesis and Antimicrobial Evaluation of Some New Oxadiazoles Derived from Phenylpropionohydrazides
Molecules 2009, 14(5), 1898-1903; doi:10.3390/molecules14051898
Received: 14 April 2009 / Revised: 12 May 2009 / Accepted: 13 May 2009 / Published: 20 May 2009
Cited by 18 | PDF Full-text (94 KB)
Abstract
In this study a series ofnew1-(2-aryl-5-phenethyl-1,3,4-oxadiazol-3(2H)-yl)ethanones 2a-e was synthesized by the cyclization of imines 1a-e using acetic anhydride. The products were evaluated for anti-bacterial and anti-fungal activity. Among the newly synthesized compounds, 1-(2-(4-(dimethylamino)phenyl)-5-phenethyl-1,3,4-oxadiazol-3(2H)-yl)ethanone (2a)and1-(2-(4-chlorophenyl)-5-phenethyl-1,3,4-oxadiazol-3(2H)-yl)ethanone (2b)were found to possess maximum activity against the
[...] Read more.
In this study a series ofnew1-(2-aryl-5-phenethyl-1,3,4-oxadiazol-3(2H)-yl)ethanones 2a-e was synthesized by the cyclization of imines 1a-e using acetic anhydride. The products were evaluated for anti-bacterial and anti-fungal activity. Among the newly synthesized compounds, 1-(2-(4-(dimethylamino)phenyl)-5-phenethyl-1,3,4-oxadiazol-3(2H)-yl)ethanone (2a)and1-(2-(4-chlorophenyl)-5-phenethyl-1,3,4-oxadiazol-3(2H)-yl)ethanone (2b)were found to possess maximum activity against the tested strains of S. aureus and P. aeruginosa. It was concluded that para-substitution enhances the activity of synthesized oxadiazoles. Full article
Open AccessArticle Synthesis and Analysis of Some Bis-Heterocyclic Compounds Containing Sulphur
Molecules 2009, 14(5), 1904-1914; doi:10.3390/molecules14051904
Received: 1 April 2009 / Revised: 15 May 2009 / Accepted: 19 May 2009 / Published: 22 May 2009
Cited by 25 | PDF Full-text (119 KB)
Abstract A facile and convenient synthesis of a series of bisheterocycles 7a,b 10, 12 and 13a,b containing a thieno[2,3-b]thiophene base unit via the versatile, hitherto unreported 3-[3,4-dimethyl-5-(3-nitrilopropanoyl)thieno[2,3-b]thiophen-2-yl]-3-oxopropanenitrile (4) is described. Full article
Open AccessCommunication Silica Bonded S-Sulfonic Acid: A Recyclable Catalyst for the Synthesis of Quinoxalines at Room Temperature
Molecules 2009, 14(5), 1915-1926; doi:10.3390/molecules14051915
Received: 26 March 2009 / Revised: 27 April 2009 / Accepted: 30 April 2009 / Published: 22 May 2009
Cited by 74 | PDF Full-text (209 KB)
Abstract
The reaction of 3-mercaptopropylsilica (MPS) and chlorosulfonic acid in chloroform afforded silica bonded S-sulfonic acid (SBSSA), which was used as a catalyst for the room temperature synthesis of quinoxaline derivatives from 1,2-diamino compounds and 1,2-dicarbonyl compounds. The catalyst could be recycled and
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The reaction of 3-mercaptopropylsilica (MPS) and chlorosulfonic acid in chloroform afforded silica bonded S-sulfonic acid (SBSSA), which was used as a catalyst for the room temperature synthesis of quinoxaline derivatives from 1,2-diamino compounds and 1,2-dicarbonyl compounds. The catalyst could be recycled and reused several times without any loss of efficiency. Full article
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Open AccessArticle New Macrocyclic Amines Showing Activity as HIV Entry Inhibitors Against Wild Type and Multi-Drug Resistant Viruses
Molecules 2009, 14(5), 1927-1937; doi:10.3390/molecules14051927
Received: 2 April 2009 / Revised: 20 May 2009 / Accepted: 21 May 2009 / Published: 22 May 2009
Cited by 4 | PDF Full-text (118 KB)
Abstract
Considering as a lead molecule the chemokine CXCR4 receptor antagonist AMD-3100, which shows significant anti-HIV activity in vitro and in vivo, we investigated a series of structurally related macrocyclic polyamines incorporating o,o’-phenanthroline or 2,2’-bipyridyl scaffolds as potential antiviral agents with lower
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Considering as a lead molecule the chemokine CXCR4 receptor antagonist AMD-3100, which shows significant anti-HIV activity in vitro and in vivo, we investigated a series of structurally related macrocyclic polyamines incorporating o,o’-phenanthroline or 2,2’-bipyridyl scaffolds as potential antiviral agents with lower toxicity and increased activity against both wild type X4-tropic and dual tropic HIV strains. The antiviral activity of these compounds was evaluated by susceptibility assays in PBMC (Peripheral Blood Mononuclear Cells) and compared to that of AMD-3100. The newly investigated compounds showed IC50s values in the low micromolar range and significantly inhibited the viral replication of wild type X4-tropic isolate and dual tropic strains. These macrocyclic polyamines constitute a promising class of HIV entry inhibitors. Full article
Open AccessArticle Efficacy of Essential Oils from Edible Plants as Insecticides Against the House Fly, Musca Domestica L.
Molecules 2009, 14(5), 1938-1947; doi:10.3390/molecules14051938
Received: 14 April 2009 / Revised: 15 May 2009 / Accepted: 18 May 2009 / Published: 25 May 2009
Cited by 53 | PDF Full-text (157 KB)
Abstract
The compositions of 12 essential oils (EOs) obtained by hydrodistillation of edible fruits and herbs were analyzed by gas chromatography/mass spectroscopy (GC/MS). The insecticidal activity of each oil against the house fly Musca domestica was evaluated by placing flies in a glass jar
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The compositions of 12 essential oils (EOs) obtained by hydrodistillation of edible fruits and herbs were analyzed by gas chromatography/mass spectroscopy (GC/MS). The insecticidal activity of each oil against the house fly Musca domestica was evaluated by placing flies in a glass jar with a screw cap that held a piece of EO-treated cotton yarn. The dose necessary to kill 50% of flies (LC50) in 30 min was determined at 26 ± 1°C. Twelve EOs and 17 individual terpenes were assayed against M. domestica, showing LC50 values ranging from 3.9 to 85.2 and from 3.3 to >100 mg/dm3, respectively. EO from Citrus sinensis was the most potent insecticide (LC50 = 3.9 mg/dm3), followed by EOs from C. aurantium (LC50 = 4.8 mg/dm3) and Eucalyptus cinerea (LC50 = 5.5 mg/dm3). According to GC/MS analysis, limonene (92.47%), linalool (1.43%), and b-myrcene (0.88%) were the principal components of C. sinensis EO. Limonene was also the principal constituent (94.07%) of C. aurantium, while 1,8-cineole (56.86%) was the major constituent of E. cinerea EO. 1,8-Cineole was most active against M. domestica (LC50 = 3.3 mg/dm3), while (4R)(+)-limonene, was moderately active (LC50 = 6.2 mg/dm3). Dimethyl 2,2-dichlorovinyl phosphate (DDVP) selected as a positive control, showed an LC50 of 0.5 mg/dm3. EOs from C. sinensis, C. aurantium, and E. cinerea show promise as natural insecticides against houseflies. Full article
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Open AccessArticle New Triterpene Saponins from Duranta repens Linn. and Their Cytotoxic Activity
Molecules 2009, 14(5), 1952-1965; doi:10.3390/molecules14051952
Received: 29 March 2009 / Revised: 8 May 2009 / Accepted: 13 May 2009 / Published: 25 May 2009
Cited by 12 | PDF Full-text (476 KB)
Abstract
From the leaves of Duranta repens (Verbenaceae) two new triterpene saponins, named durantanin IV (1) and V (2)were isolated.In addition, ten known compounds were isolated, namely a bidesmosidic saponin, oleanolic acid, three phenylethanoids and five flavonoids. All metabolites were isolated for the first
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From the leaves of Duranta repens (Verbenaceae) two new triterpene saponins, named durantanin IV (1) and V (2)were isolated.In addition, ten known compounds were isolated, namely a bidesmosidic saponin, oleanolic acid, three phenylethanoids and five flavonoids. All metabolites were isolated for the first time from this genus except for 3 (oleanolic acid) and 7 (E/Z acteoside). The structures were determined mainly by spectroscopic methods (UV, IR, HRESI-MS, 1H-, 13C-NMR, 1H-1H COSY, HSQC and HMBC). Cytotoxic screening of the chloroform, ethyl acetate and methanol extracts was carried out on brine shrimps. In addition, the investigated methanol extract and compounds 1, 2 and 7 showed significant cytotoxic activity against a HepG2 cell line. Full article

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Open AccessReview Recent Developments in the Chemistry of Deoxyribonucleic Acid (DNA) Intercalators: Principles, Design, Synthesis, Applications and Trends
Molecules 2009, 14(5), 1725-1746; doi:10.3390/molecules14051725
Received: 15 February 2009 / Revised: 20 April 2009 / Accepted: 5 May 2009 / Published: 7 May 2009
Cited by 77 | PDF Full-text (236 KB)
Abstract
In the present overview, we describe the bases of intercalation of small molecules (cationic and polar neutral compounds) in DNA. We briefly describe the importance of DNA structure and principles of intercalation. Selected syntheses, possibilities and applications are shown to exemplify the importance,
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In the present overview, we describe the bases of intercalation of small molecules (cationic and polar neutral compounds) in DNA. We briefly describe the importance of DNA structure and principles of intercalation. Selected syntheses, possibilities and applications are shown to exemplify the importance, drawbacks and challenges in this pertinent, new, and exciting research area. Additionally, some clinical applications (molecular processes, cancer therapy and others) and trends are described. Full article
(This article belongs to the Special Issue Nucleic Acids)
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Open AccessReview Evodiamine: A Novel Anti-Cancer Alkaloid from Evodia rutaecarpa
Molecules 2009, 14(5), 1852-1859; doi:10.3390/molecules14051852
Received: 20 April 2009 / Revised: 4 May 2009 / Accepted: 7 May 2009 / Published: 18 May 2009
Cited by 72 | PDF Full-text (48 KB)
Abstract
Traditional Chinese herbs are regarded as a new and promising source of potential anti-cancer remedies and new chemotherapy adjuvants to enhance the efficacy of chemotherapy and/or to ameliorate its side effects. Extensive investigations have been undertaken both in the experimental and clinical studies
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Traditional Chinese herbs are regarded as a new and promising source of potential anti-cancer remedies and new chemotherapy adjuvants to enhance the efficacy of chemotherapy and/or to ameliorate its side effects. Extensive investigations have been undertaken both in the experimental and clinical studies over the years to augment the efficacy of chemotherapy. Evodia rutaecarpa is a very popular multi-purpose herb traditionally used in China for the treatment of headaches, abdominal pain, postpartum hemorrhage, dysentery and amenorrhea. The major constituents of Evodia rutaecarpa are evodiamine and rutaecarpine. Growing evidence demonstrates that evodiamine possesses anti-cancer activities both in vitro and in vivo by inhibiting proliferation, invasion and metastasis, inducing apoptosis of a variety of tumor cell lines. This review is aimed to summarize the recent researches on evodiamine focusing on anti-cancer activity and to highlight molecular mechanisms during the past ten years. Full article

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Open AccessCorrection Correction: Eleni, M. et al. High Quality Bergamot Oil from Greece: Chemical Analysis Using Chiral Gas Chromatography and Larvicidal Activity against the West Nile Virus Vector. Molecules 2009, 14(2), 839-849
Molecules 2009, 14(5), 1948-1949; doi:10.3390/molecules14051948
Received: 14 May 2009 / Published: 25 May 2009
PDF Full-text (17 KB)
Abstract In the original published version of this paper [1], the given names and surnames of the coauthors were accidently inverted, and should be as indicated below: [...] Full article
Open AccessCorrection Corrections: “Synthesis of Sulfonamides and Evaluation of Their Histone Deacetylase (HDAC) Activity” by Jung et al., Molecules 2007, 12, 1125-1135
Molecules 2009, 14(5), 1950-1951; doi:10.3390/molecules14051950
Received: 14 April 2009 / Published: 25 May 2009
PDF Full-text (18 KB)
Abstract At the request of the authors of this paper [1], we wish to announce the following corrections: [...] Full article

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