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Molecules, Volume 14, Issue 10 (October 2009), Pages 3844-4299

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Open AccessReview Sonoelectrochemical Synthesis of Nanoparticles
Molecules 2009, 14(10), 4284-4299; https://doi.org/10.3390/molecules14104284
Received: 30 September 2009 / Revised: 22 October 2009 / Accepted: 23 October 2009 / Published: 23 October 2009
Cited by 96 | PDF Full-text (332 KB)
Abstract
This article reviews the nanomaterials that have been prepared to date by pulsed sonoelectrochemistry. The majority of nanomaterials produced by this method are pure metals such as silver, palladium, platinum, zinc, nickel and gold, but more recently the syntheses have been extended to
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This article reviews the nanomaterials that have been prepared to date by pulsed sonoelectrochemistry. The majority of nanomaterials produced by this method are pure metals such as silver, palladium, platinum, zinc, nickel and gold, but more recently the syntheses have been extended to include the preparation of nanosized metallic alloys and metal oxide semiconductors. A major advantage of this methodology is that the shape andsize of the nanoparticles can be adjusted by varying the operating parameters which include ultrasonic power, current density, deposition potential and the ultrasonic vs electrochemical pulse times. Together with these, it is also possible to adjust the pH, temperature and composition of the electrolyte in the sonoelectrochemistry cell. Full article
(This article belongs to the Special Issue Sonochemistry-organic synthesis)
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Open AccessCommunication Preparation of (S)-1-Halo-2-octanols Using Ionic Liquids and Biocatalysts
Molecules 2009, 14(10), 4275-4283; https://doi.org/10.3390/molecules14104275
Received: 31 August 2009 / Revised: 26 September 2009 / Accepted: 16 October 2009 / Published: 23 October 2009
Cited by 5 | PDF Full-text (192 KB)
Abstract
Preparation of (S)-1-chloro-2-octanol and (S)-1-bromo-2-octanol was carried out by the enzymatic hydrolysis of halohydrin palmitates using biocatalysts. Halohydrin palmitates were prepared by various methods from palmitic acid and 1,2-octanediol. A tandem hydrolysis was carried out using lipases from Candida
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Preparation of (S)-1-chloro-2-octanol and (S)-1-bromo-2-octanol was carried out by the enzymatic hydrolysis of halohydrin palmitates using biocatalysts. Halohydrin palmitates were prepared by various methods from palmitic acid and 1,2-octanediol. A tandem hydrolysis was carried out using lipases from Candida antarctica (Novozym® 435), Rhizomucor miehei (Lipozyme IM), and “resting cells” from a Rhizopus oryzae strain that was not mycotoxigenic. The influence of the enzyme and the reaction medium on the selective hydrolysis of isomeric mixtures of halohydrin esters is described. Novozym® 435 allowed preparation of (S)-1-chloro-2-octanol and (S)-1-bromo-2-octanol after 1–3 h of reaction at 40 °C in [BMIM][PF6]. Full article
(This article belongs to the collection Ionic Liquids)
Open AccessArticle An Unsymmetrical Tetrathiafulvalene with a Fused 1,2,5-Thiadiazole Ring and Methylthio Groups
Molecules 2009, 14(10), 4266-4274; https://doi.org/10.3390/molecules14104266
Received: 27 August 2009 / Revised: 21 October 2009 / Accepted: 23 October 2009 / Published: 23 October 2009
PDF Full-text (330 KB)
Abstract
The title compound, 5-(4,5-dimethylthio-1,3-dithiol-2-ylidene)-1,3-diaza-2,4,6-trithiapentalene (4,5-dimethylthio [1,2,5]thiadiazolotetrathiafulvalene, molecular formula C8H6N2S7) crystallizes in the P21/n space group with one molecule in the asymmetric unit. The molecular framework is planar within 0.19 Å. The molecules
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The title compound, 5-(4,5-dimethylthio-1,3-dithiol-2-ylidene)-1,3-diaza-2,4,6-trithiapentalene (4,5-dimethylthio [1,2,5]thiadiazolotetrathiafulvalene, molecular formula C8H6N2S7) crystallizes in the P21/n space group with one molecule in the asymmetric unit. The molecular framework is planar within 0.19 Å. The molecules form a head-to-tail type of π-stacking dimer with an interplanar distance is 3.50(1) Å, where methylthio groups face away from each other. The molecules are also linked by weak intermolecular S···S heteroatom interactions [3.497(1) and 3.572(1) Å] to construct a unique one-dimensional molecular tape structure. Full article
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Open AccessArticle Investigating Biological Activity Spectrum for Novel Styrylquinazoline Analogues
Molecules 2009, 14(10), 4246-4265; https://doi.org/10.3390/molecules14104246
Received: 21 September 2009 / Revised: 13 October 2009 / Accepted: 21 October 2009 / Published: 23 October 2009
Cited by 28 | PDF Full-text (194 KB)
Abstract
In this study, series of ring-substituted 2-styrylquinazolin-4(3H)-one and 4-chloro-2-styrylquinazoline derivatives were prepared. The syntheses of the discussed compounds are presented. The compounds were analyzed by RP-HPLC to determine lipophilicity. They were tested for their inhibitory activity on photosynthetic electron transport (PET)
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In this study, series of ring-substituted 2-styrylquinazolin-4(3H)-one and 4-chloro-2-styrylquinazoline derivatives were prepared. The syntheses of the discussed compounds are presented. The compounds were analyzed by RP-HPLC to determine lipophilicity. They were tested for their inhibitory activity on photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four mycobacterial strains and against eight fungal strains. Several compounds showed biological activity comparable with or higher than that of the standard isoniazid. It was found that the electronic properties of the R substituent, and not the total lipophilicity of the compound, were decisive for the photosynthesis-inhibiting activity of tested compounds. Full article
Open AccessArticle Soft Alkyl Ether Prodrugs of a Model Phenolic Drug: The Effect of Incorporation of Ethyleneoxy Groups on Transdermal Delivery
Molecules 2009, 14(10), 4231-4245; https://doi.org/10.3390/molecules14104231
Received: 18 September 2009 / Revised: 13 October 2009 / Accepted: 19 October 2009 / Published: 22 October 2009
Cited by 10 | PDF Full-text (139 KB)
Abstract
Two different types of soft alkyl ether prodrugs incorporating ethyleneoxy groups into the promoiety have been synthesized for a model phenol (acetaminophen, APAP): alkyloxycarbonyloxymethyl type (AOCOM) and N-alkyl-N-alkyloxycarbonyl-aminomethyl type (NANAOCAM). The solubilities in isopropyl myristate, SIPM, and water,
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Two different types of soft alkyl ether prodrugs incorporating ethyleneoxy groups into the promoiety have been synthesized for a model phenol (acetaminophen, APAP): alkyloxycarbonyloxymethyl type (AOCOM) and N-alkyl-N-alkyloxycarbonyl-aminomethyl type (NANAOCAM). The solubilities in isopropyl myristate, SIPM, and water, SAQ, partition coefficients between IPM and pH 4.0 buffer, KIPM:4.0, and the delivery of total species containing APAP through hairless mouse skin from IPM, JMMIPM, have been measured for the prodrugs. The JMMIPM values were accurately predicted by the Roberts-Sloan (RS) equation. Only modest increases in JMMIPM were realized (about 1.4 times) by each type. The only prodrug that was more water soluble and more lipid soluble than APAP did not improve JMMIPM of APAP. This result may be due to the strong association of water molecules with the ethyleneoxy groups, and especially the triethyleneoxy derivative, which dramatically increases the molecular weight and depresses JMMIPM. Full article
(This article belongs to the Special Issue Prodrugs)
Open AccessArticle Chemical Composition and in Vitro Antimicrobial and Mutagenic Activities of Seven Lamiaceae Essential Oils
Molecules 2009, 14(10), 4213-4230; https://doi.org/10.3390/molecules14104213
Received: 6 October 2009 / Revised: 20 October 2009 / Accepted: 20 October 2009 / Published: 20 October 2009
Cited by 54 | PDF Full-text (481 KB)
Abstract
Deeper knowledge of the potentiality of aromatic plants can provide results of economic importance for food and pharmacological industry. The essential oils of seven Lamiaceae species were analyzed by gas chromatography-mass spectrometry and assayed for their antibacterial, antifungal and mutagenic activities. Monoterpenes in
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Deeper knowledge of the potentiality of aromatic plants can provide results of economic importance for food and pharmacological industry. The essential oils of seven Lamiaceae species were analyzed by gas chromatography-mass spectrometry and assayed for their antibacterial, antifungal and mutagenic activities. Monoterpenes in the oils ranged between 82.47% (hyssop oil) and 97.48% (thyme oil), being mainly represented by oxygenated compounds. The antibacterial activity was evaluated against six pathogenic and five non-pathogenic bacterial strains. Oregano and thyme oils showed the strongest antibacterial activity against the pathogenic ones. The antifungal activity was evaluated against six fungal strains of agrifood interest: the oils tested exhibited variable degrees of activity. Two Salmonella typhimurium strains were used to assess the possible mutagenic activity. No oil showed mutagenic activity. Data obtained let us hypothesise that the use of essential oils could be a viable and safe way to decrease the utilisation of synthetic food preservatives. Further research is needed to obtain information regarding the practical effectiveness of essential oils to prevent the growth of food borne and spoiling microbes under specific application conditions. Full article
Open AccessArticle Rhodanineacetic Acid Derivatives as Potential Drugs: Preparation, Hydrophobic Properties and Antifungal Activity of (5-Arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic Acids
Molecules 2009, 14(10), 4197-4212; https://doi.org/10.3390/molecules14104197
Received: 21 September 2009 / Revised: 9 October 2009 / Accepted: 19 October 2009 / Published: 20 October 2009
Cited by 28 | PDF Full-text (270 KB)
Abstract
Some [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acids were prepared as potential antifungal compounds. The general synthetic approach to all synthesized compounds is presented. Lipophilicity of all the discussed rhodanine-3-acetic acid derivatives was analyzed using a reversed phase high performance liquid chromatography (RP-HPLC) method. The procedure
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Some [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acids were prepared as potential antifungal compounds. The general synthetic approach to all synthesized compounds is presented. Lipophilicity of all the discussed rhodanine-3-acetic acid derivatives was analyzed using a reversed phase high performance liquid chromatography (RP-HPLC) method. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary RP column. The RP-HPLC retention parameter log k (the logarithm of the capacity factor k) is compared with log P values calculated in silico. All compounds were evaluated for antifungal effects against selected fungal species. Most compounds exhibited no interesting activity, and only {(5Z)-[4-oxo-5-(pyridin-2- ylmethylidene)-2-thioxo-1,3-thiazolidin-3-yl]}acetic acid strongly inhibited the growth of Candida tropicalis 156, Candida krusei E 28, Candida glabrata 20/I and Trichosporon asahii 1188. Full article
(This article belongs to the Special Issue ECSOC-12)
Open AccessArticle New Flavonoid Glycosides from Elsholtzia rugulosa Hemsl.
Molecules 2009, 14(10), 4190-4196; https://doi.org/10.3390/molecules14104190
Received: 21 September 2009 / Revised: 12 October 2009 / Accepted: 20 October 2009 / Published: 20 October 2009
Cited by 22 | PDF Full-text (178 KB)
Abstract
Elsholtzia rugulosa Hemsl. is known in China as a local herbal tea, medicinal herb and honey plant. Chemical examination of E. rugulosa led to the isolation of two new flavonoid glycosides, apigenin 4'-O-α-D-glucopyranoside (1) and 5,7,3',4'-tetrahydroxy-5'-C-prenylflavone-7-O-β
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Elsholtzia rugulosa Hemsl. is known in China as a local herbal tea, medicinal herb and honey plant. Chemical examination of E. rugulosa led to the isolation of two new flavonoid glycosides, apigenin 4'-O-α-D-glucopyranoside (1) and 5,7,3',4'-tetrahydroxy-5'-C-prenylflavone-7-O-β-D-glucopyranoside (2), together with nine known flavonoids. Their structures were elucidated on the basis of spectroscopic evidence. Full article
Open AccessArticle Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation
Molecules 2009, 14(10), 4180-4189; https://doi.org/10.3390/molecules14104180
Received: 8 September 2009 / Revised: 1 October 2009 / Accepted: 13 October 2009 / Published: 20 October 2009
Cited by 20 | PDF Full-text (458 KB)
Abstract
The condensation of chlorides of substituted pyrazinecarboxylic acids with ringsubstituted anilines yielded twelve substituted pyrazinecarboxylic acid amides. The synthetic approach, analytical, and lipophilicity data of the newly synthesized compounds are presented. Two antituberculosis assays were used. Firstly, the antimycobacterial activity against four different
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The condensation of chlorides of substituted pyrazinecarboxylic acids with ringsubstituted anilines yielded twelve substituted pyrazinecarboxylic acid amides. The synthetic approach, analytical, and lipophilicity data of the newly synthesized compounds are presented. Two antituberculosis assays were used. Firstly, the antimycobacterial activity against four different Mycobacterium strains in a series of pyrazine derivatives was investigated. Secondly, the antimycobacterial evaluation was performed at the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF) program. Interesting in vitro antimycobacterial activity was found, N-(3-iodo-4-methylphenyl) pyrazine-2-carboxamide (9) was most active derivative compound against M. tuberculosis (MIC < 2.0 μmol/L), while another iodo derivative 5-tert-butyl-6-chloro-N-(3-iodo-4-methyl-phenyl)pyrazine-2-carboxamide (12) was the most active compound in the TAACF antituberculosis screening program (IC90 = 0.819 μg/mL). Full article
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Open AccessArticle Design and Synthesis of Novel 2-Phenylaminopyrimidine (PAP) Derivatives and Their Antiproliferative Effects in Human Chronic Myeloid Leukemia Cells
Molecules 2009, 14(10), 4166-4179; https://doi.org/10.3390/molecules14104166
Received: 1 September 2009 / Revised: 30 September 2009 / Accepted: 12 October 2009 / Published: 19 October 2009
Cited by 13 | PDF Full-text (381 KB)
Abstract
A series of novel 2-phenylaminopyrimidine (PAP) derivatives structurally related to STI-571 were designed and synthesized. The abilities of these compounds to inhibit proliferation were tested in human chronic myeloid leukemia K562 cells. (E)-3-(2-bromophenyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)phenyl]acrylamide(12d) was the most effective cell growth
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A series of novel 2-phenylaminopyrimidine (PAP) derivatives structurally related to STI-571 were designed and synthesized. The abilities of these compounds to inhibit proliferation were tested in human chronic myeloid leukemia K562 cells. (E)-3-(2-bromophenyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)phenyl]acrylamide(12d) was the most effective cell growth inhibitor and was 3-fold more potent than STI-571. Full article
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Open AccessCommunication Trametes sp. as a Source of Biopolymer Cross-Linking Agents: Laccase Induced Gelation of Ferulated Arabinoxylans
Molecules 2009, 14(10), 4159-4165; https://doi.org/10.3390/molecules14104159
Received: 10 September 2009 / Revised: 16 October 2009 / Accepted: 16 October 2009 / Published: 16 October 2009
PDF Full-text (118 KB)
Abstract
This study examined the feasibility of using Trametes sp. grown under drought conditions to catalyze the covalent cross-linking of ferulated arabinoxylans. The rate of polymerization of ferulated arabinoxylans solutions at 0.5% (w/v) was dose dependent on the laccase concentration in the system. Above
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This study examined the feasibility of using Trametes sp. grown under drought conditions to catalyze the covalent cross-linking of ferulated arabinoxylans. The rate of polymerization of ferulated arabinoxylans solutions at 0.5% (w/v) was dose dependent on the laccase concentration in the system. Above 1.2 nkat laccase/mg ferulated arabinoxylan, the rate of cross-linking reached a plateau, suggesting that the reaction reached saturation. For 2% (w/v) ferulated arabinoxylans treated with laccase (1.6 nkat/mg ferulated arabinoxylan), stable gels were formed after 4 h at 25 °C, with cross-linking contents (diferulic and triferulic acid) contents of 0.03 and 0.015 μg/mg ferulated arabinoxylan, respectively. This study demonstrated that Trametes sp. can be a source of biopolymer cross-linking enzymes like laccase. Full article
Open AccessArticle Structural Investigation of Biologically Active Phenolic Compounds Isolated from European Tree Species
Molecules 2009, 14(10), 4147-4158; https://doi.org/10.3390/molecules14104147
Received: 14 August 2009 / Revised: 2 October 2009 / Accepted: 14 October 2009 / Published: 16 October 2009
Cited by 9 | PDF Full-text (327 KB)
Abstract
X-ray structures of two compounds isolated from wood knots of coniferous trees, namely dihydrokaempferol (3,5,8,13-tetrahydroxyflavanon) and lariciresinol (3,14-dimetoxy-7,10-epoxylignan-4,15,19-triol), are presented here. Diffraction data for the Dihydrokaempferol crystals were collected on a CAD4 diffractometer and on a synchrotron for the lariciresinol crystal. The investigated
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X-ray structures of two compounds isolated from wood knots of coniferous trees, namely dihydrokaempferol (3,5,8,13-tetrahydroxyflavanon) and lariciresinol (3,14-dimetoxy-7,10-epoxylignan-4,15,19-triol), are presented here. Diffraction data for the Dihydrokaempferol crystals were collected on a CAD4 diffractometer and on a synchrotron for the lariciresinol crystal. The investigated compounds inhibit lipid peroxidation and lariciresinol is additionally a good scavenger of superoxide radicals. The structural data presented in this work provide a useful basis for designing more active compounds with potential use as antioxidants. Full article
Open AccessArticle Characterization of Primary Standards for Use in the HPLC Analysis of the Procyanidin Content of Cocoa and Chocolate Containing Products
Molecules 2009, 14(10), 4136-4146; https://doi.org/10.3390/molecules14104136
Received: 5 August 2009 / Revised: 25 August 2009 / Accepted: 30 September 2009 / Published: 15 October 2009
Cited by 21 | PDF Full-text (200 KB)
Abstract
This report describes the characterization of a series of commercially available procyanidin standards ranging from dimers DP = 2 to decamers DP = 10 for the determination of procyanidins from cocoa and chocolate. Using a combination of HPLC with fluorescence detection and MALDI-TOF
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This report describes the characterization of a series of commercially available procyanidin standards ranging from dimers DP = 2 to decamers DP = 10 for the determination of procyanidins from cocoa and chocolate. Using a combination of HPLC with fluorescence detection and MALDI-TOF mass spectrometry, the purity of each standard was determined and these data were used to determine relative response factors. These response factors were compared with other response factors obtained from published methods. Data comparing the procyanidin analysis of a commercially available US dark chocolate calculated using each of the calibration methods indicates divergent results and demonstrate that previous methods may significantly underreport the procyanidins in cocoa-containing products. These results have far reaching implications because the previous calibration methods have been used to develop data for a variety of scientific reports, including food databases and clinical studies. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle New 1-Aryl-3-Substituted Propanol Derivatives as Antimalarial Agents
Molecules 2009, 14(10), 4120-4135; https://doi.org/10.3390/molecules14104120
Received: 11 August 2009 / Revised: 21 September 2009 / Accepted: 14 October 2009 / Published: 14 October 2009
Cited by 13 | PDF Full-text (147 KB)
Abstract
This paper describes the synthesis and in vitro antimalarial activity against a P. falciparum 3D7 strain of some new 1-aryl-3-substituted propanol derivatives. Twelve of the tested compounds showed an IC50 lower than 1 μM. These compounds were also tested for cytotoxicity in
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This paper describes the synthesis and in vitro antimalarial activity against a P. falciparum 3D7 strain of some new 1-aryl-3-substituted propanol derivatives. Twelve of the tested compounds showed an IC50 lower than 1 μM. These compounds were also tested for cytotoxicity in murine J774 macrophages. The most active compounds were evaluated for in vivo activity against P. berghei in a 4-day suppressive test. Compound 12 inhibited more than 50% of parasite growth at a dose of 50 mg/kg/day. In addition, an FBIT test was performed to measure the ability to inhibit ferriprotoporphyrin biocrystallization. This data indicates that 1-aryl-3-substituted propanol derivatives hold promise as a new therapeutic option for the treatment of malaria. Full article
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Open AccessReview Addition and Cycloaddition Reactions of Phosphinyl- and Phosphonyl-2H-Azirines, Nitrosoalkenes and Azoalkenes
Molecules 2009, 14(10), 4098-4119; https://doi.org/10.3390/molecules14104098
Received: 25 August 2009 / Revised: 23 September 2009 / Accepted: 12 October 2009 / Published: 13 October 2009
Cited by 39 | PDF Full-text (460 KB)
Abstract
An overview of the use of 2H-azirines, conjugated nitrosoalkenes and conjugated azoalkenes bearing phosphorus substituents in addition and cycloaddition reactions is presented, focused on strategies for the synthesis of aminophosphonate and aminophosphine oxide derivatives. Full article
(This article belongs to the Special Issue Alpha- or Beta-aminophosphonates and -phosphinates)
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