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Molecules, Volume 14, Issue 9 (September 2009), Pages 3115-3843

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Open AccessCommunication Amides from Piper capense with CNS Activity – A Preliminary SAR Analysis
Molecules 2009, 14(9), 3833-3843; https://doi.org/10.3390/molecules14093833
Received: 8 September 2009 / Revised: 25 September 2009 / Accepted: 25 September 2009 / Published: 25 September 2009
Cited by 20 | Viewed by 11101 | PDF Full-text (322 KB)
Abstract
Piper capense L.f. (Piperaceae) is used traditionally in South Africa as a sleep inducing remedy. Bioassay-guided fractionation of the roots of P. capense led to the isolation of piperine (1) and 4,5-dihydropiperine (2), which showed moderate affinity for the benzodiazepine site on the
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Piper capense L.f. (Piperaceae) is used traditionally in South Africa as a sleep inducing remedy. Bioassay-guided fractionation of the roots of P. capense led to the isolation of piperine (1) and 4,5-dihydropiperine (2), which showed moderate affinity for the benzodiazepine site on the GABAA receptor (IC50 values of 1.2 mM and 1.0 mM, respectively). The present study suggests that strict structural properties of the amides are essential for affinity. Taken together, these observations suggest that the carbon chain must contain not less than four carbons, and that a conjugated double bond, adjacent to the amide group, is necessary for binding to the receptor and that the amine part should be bulky. Full article
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Open AccessArticle Heterocyclic Analogs of Thioflavones: Synthesis and NMR Spectroscopic Investigations
Molecules 2009, 14(9), 3814-3832; https://doi.org/10.3390/molecules14093814
Received: 3 September 2009 / Revised: 11 September 2009 / Accepted: 21 September 2009 / Published: 25 September 2009
Cited by 27 | Viewed by 7738 | PDF Full-text (213 KB)
Abstract
The synthesis of several hitherto unknown heterocyclic ring systems derived from thioflavone is described. Coupling of various o-haloheteroarenecarbonyl chlorides with phenylacetylene gives 1-(o-haloheteroaryl)-3-phenylprop-2-yn-1-ones, which were treated with NaSH in refluxing ethanol to yield the corresponding bi- and tricyclic annelated 2-phenylthiopyran-4-ones.
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The synthesis of several hitherto unknown heterocyclic ring systems derived from thioflavone is described. Coupling of various o-haloheteroarenecarbonyl chlorides with phenylacetylene gives 1-(o-haloheteroaryl)-3-phenylprop-2-yn-1-ones, which were treated with NaSH in refluxing ethanol to yield the corresponding bi- and tricyclic annelated 2-phenylthiopyran-4-ones. Detailed NMR spectroscopic investigations of the ring systems and their precursors are presented. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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Open AccessReview On the Chemical Stabilities of Ionic Liquids
Molecules 2009, 14(9), 3780-3813; https://doi.org/10.3390/molecules14093780
Received: 1 July 2009 / Revised: 16 September 2009 / Accepted: 18 September 2009 / Published: 25 September 2009
Cited by 271 | Viewed by 14134 | PDF Full-text (365 KB)
Abstract
Ionic liquids are novel solvents of interest as greener alternatives to conventional organic solvents aimed at facilitating sustainable chemistry. As a consequence of their unusual physical properties, reusability, and eco-friendly nature, ionic liquids have attracted the attention of organic chemists. Numerous reports have
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Ionic liquids are novel solvents of interest as greener alternatives to conventional organic solvents aimed at facilitating sustainable chemistry. As a consequence of their unusual physical properties, reusability, and eco-friendly nature, ionic liquids have attracted the attention of organic chemists. Numerous reports have revealed that many catalysts and reagents were supported in the ionic liquid phase, resulting in enhanced reactivity and selectivity in various important reaction transformations. However, synthetic chemists cannot ignore the stability data and intermolecular interactions, or even reactions that are directly applicable to organic reactions in ionic liquids. It is becoming evident from the increasing number of reports on use of ionic liquids as solvents, catalysts, and reagents in organic synthesis that they are not totally inert under many reaction conditions. While in some cases, their unexpected reactivity has proven fortuitous and in others, it is imperative that when selecting an ionic liquid for a particular synthetic application, attention must be paid to its compatibility with the reaction conditions. Even though, more than 200 room temperature ionic liquids are known, only a few reports have commented their effects on reaction mechanisms or rate/stability. Therefore, rather than attempting to give a comprehensive overview of ionic liquid chemistry, this review focuses on the non-innocent nature of ionic liquids, with a decided emphasis to clearly illuminate the ability of ionic liquids to affect the mechanistic aspects of some organic reactions thereby affecting and promoting the yield and selectivity. Full article
(This article belongs to the collection Ionic Liquids)
Open AccessReview Nasal Delivery of High Molecular Weight Drugs
Molecules 2009, 14(9), 3754-3779; https://doi.org/10.3390/molecules14093754
Received: 21 July 2009 / Revised: 14 September 2009 / Accepted: 17 September 2009 / Published: 23 September 2009
Cited by 74 | Viewed by 12455 | PDF Full-text (495 KB)
Abstract
Nasal drug delivery may be used for either local or systemic effects. Low molecular weight drugs with are rapidly absorbed through nasal mucosa. The main reasons for this are the high permeability, fairly wide absorption area, porous and thin endothelial basement membrane of
[...] Read more.
Nasal drug delivery may be used for either local or systemic effects. Low molecular weight drugs with are rapidly absorbed through nasal mucosa. The main reasons for this are the high permeability, fairly wide absorption area, porous and thin endothelial basement membrane of the nasal epithelium. Despite the many advantages of the nasal route, limitations such as the high molecular weight (HMW) of drugs may impede drug absorption through the nasal mucosa. Recent studies have focused particularly on the nasal application of HMW therapeutic agents such as peptide-protein drugs and vaccines intended for systemic effects. Due to their hydrophilic structure, the nasal bioavailability of peptide and protein drugs is normally less than 1%. Besides their weak mucosal membrane permeability and enzymatic degradation in nasal mucosa, these drugs are rapidly cleared from the nasal cavity after administration because of mucociliary clearance. There are many approaches for increasing the residence time of drug formulations in the nasal cavity resulting in enhanced drug absorption. In this review article, nasal route and transport mechanisms across the nasal mucosa will be briefly presented. In the second part, current studies regarding the nasal application of macromolecular drugs and vaccines with nanoand micro-particulate carrier systems will be summarised. Full article
(This article belongs to the Special Issue Macromolecules Applied to Pharmaceutics)
Open AccessArticle Dendrimer-Capped Nanoparticles Prepared by Picosecond Laser Ablation in Liquid Environment
Molecules 2009, 14(9), 3731-3753; https://doi.org/10.3390/molecules14093731
Received: 27 August 2009 / Revised: 17 September 2009 / Accepted: 21 September 2009 / Published: 22 September 2009
Cited by 17 | Viewed by 6642 | PDF Full-text (1646 KB)
Abstract
Fifth generation ethylendiamine-core poly(amidoamine) (PAMAM G5) is presented as an efficient capping agent for the preparation of metal and semiconductor nanoparticles by ps laser ablation in water. In particular, we describe results obtained with the fundamental, second and third harmonic of a ps
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Fifth generation ethylendiamine-core poly(amidoamine) (PAMAM G5) is presented as an efficient capping agent for the preparation of metal and semiconductor nanoparticles by ps laser ablation in water. In particular, we describe results obtained with the fundamental, second and third harmonic of a ps Nd:YAG laser and the influence of laser wavelength and pulse energy on gold particle production and subsequent photofragmentation. In this framework, the role of the dendrimer and, in particular, its interactions with gold clusters and cations are accounted. Full article
(This article belongs to the Special Issue Dendrimers - from Synthesis to Applications)
Open AccessReview Carbosilane and Carbosiloxane Dendrimers
Molecules 2009, 14(9), 3719-3730; https://doi.org/10.3390/molecules14093719
Received: 1 September 2009 / Revised: 10 September 2009 / Accepted: 15 September 2009 / Published: 22 September 2009
Cited by 8 | Viewed by 8412 | PDF Full-text (247 KB)
Abstract
This review focuses on novel carbosilane dendrimers containing branches with Si-C and Si-O-C bonds. Introduction of organic moieties into the dendrimers is performed by hydrosilation of carbon-carbon double/triple bonds. Versatile organic or organometallic moieties are introduced onto the peripheral regions of dendrimers by
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This review focuses on novel carbosilane dendrimers containing branches with Si-C and Si-O-C bonds. Introduction of organic moieties into the dendrimers is performed by hydrosilation of carbon-carbon double/triple bonds. Versatile organic or organometallic moieties are introduced onto the peripheral regions of dendrimers by coupling and complexation reactions, which clearly demonstrates their potential for variation. Full article
(This article belongs to the Special Issue Dendrimers - from Synthesis to Applications)
Open AccessArticle Theoretical Study on Exciton Dynamics in Dendritic Systems: Exciton Recurrence and Migration
Molecules 2009, 14(9), 3700-3718; https://doi.org/10.3390/molecules14093700
Received: 25 August 2009 / Revised: 11 September 2009 / Accepted: 21 September 2009 / Published: 22 September 2009
Cited by 7 | Viewed by 9228 | PDF Full-text (922 KB)
Abstract
The optical functionalities such as exciton recurrence and migration for dendritic systems, e.g., dendrimers, are investigated using the quantum master equation (QME) approach based on the ab initio molecular orbital configuration interaction (MOCI) method, which can treat both the coherent and incoherent exciton
[...] Read more.
The optical functionalities such as exciton recurrence and migration for dendritic systems, e.g., dendrimers, are investigated using the quantum master equation (QME) approach based on the ab initio molecular orbital configuration interaction (MOCI) method, which can treat both the coherent and incoherent exciton dynamics at the first principle level. Two types of phenylacetylene dendrimers, Cayley-tree dendrimer and nanostar dendrimer with anthracene core, are examined to elucidate the features of excion recurrence and migration motions in relation to their structural dependences. It is found that the nanostar dendrimer exhibits faster exciton migration from the periphery to the core than Cayley-tree dendrimer, which alternatively exhibits exciton recurrence motion among dendron parts in case of small relaxation parameters. Such strong structural dependence of exciton dynamics demonstrates the advantage of dendritic molecular systems for future applications in nano-optical and light-harvesting devices. Full article
(This article belongs to the Special Issue Dendrimers - from Synthesis to Applications)
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Open AccessArticle A New Cytotoxic 19-Nor-cardenolide from the Latex of Antiaris toxicaria
Molecules 2009, 14(9), 3694-3699; https://doi.org/10.3390/molecules14093694
Received: 22 July 2009 / Revised: 8 September 2009 / Accepted: 15 September 2009 / Published: 21 September 2009
Cited by 15 | Viewed by 6432 | PDF Full-text (143 KB)
Abstract
A new nor-cardenolide, named toxicarioside H (1), was isolated from the latex of Antiaris toxicaria (Pers.) Lesch (Moraceae). Its structure was elucidated on the basis of HRFAB-MS and spectroscopic techniques (IR, UV, 1D and 2D NMR). Compound 1 showed significant cytotoxicity against K562,
[...] Read more.
A new nor-cardenolide, named toxicarioside H (1), was isolated from the latex of Antiaris toxicaria (Pers.) Lesch (Moraceae). Its structure was elucidated on the basis of HRFAB-MS and spectroscopic techniques (IR, UV, 1D and 2D NMR). Compound 1 showed significant cytotoxicity against K562, SGC-7901, SMMC-7721, and HeLa cell lines in vitro by MTT method. Full article
Open AccessCommunication Synthesis of Novel Asymmetric Zinc (II) Phthalocyanines Bearing Octadecyloxyl and Glucosyl Groups
Molecules 2009, 14(9), 3688-3693; https://doi.org/10.3390/molecules14093688
Received: 23 July 2009 / Revised: 31 August 2009 / Accepted: 8 September 2009 / Published: 18 September 2009
Cited by 7 | Viewed by 4490 | PDF Full-text (371 KB)
Abstract
A novel asymmetric zinc (II) phthalocyanine substituted by one lipophilic octadecyloxyl group and three hydrophilic glucosyl groups was synthesized. Using Q-TOF MS, the major byproducts formed during the deprotection processes were identified. An improved procedure was worked out to convert these byproducts to
[...] Read more.
A novel asymmetric zinc (II) phthalocyanine substituted by one lipophilic octadecyloxyl group and three hydrophilic glucosyl groups was synthesized. Using Q-TOF MS, the major byproducts formed during the deprotection processes were identified. An improved procedure was worked out to convert these byproducts to the desired product in quantitative yield. Full article
Open AccessArticle Synthesis and Antifungal Activity of 5-Chloro-6-Phenylpyridazin-3(2H)-one Derivatives
Molecules 2009, 14(9), 3676-3687; https://doi.org/10.3390/molecules14093676
Received: 27 July 2009 / Revised: 13 September 2009 / Accepted: 16 September 2009 / Published: 18 September 2009
Cited by 15 | Viewed by 7911 | PDF Full-text (486 KB)
Abstract
An effective method has been developed for the preparation under mild conditions of novel pyridazine derivatives from the easily accessible starting materials mucochloric acid and benzene. All the synthesized compounds were fully characterized and some of them displayed good antifungal activities against G.
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An effective method has been developed for the preparation under mild conditions of novel pyridazine derivatives from the easily accessible starting materials mucochloric acid and benzene. All the synthesized compounds were fully characterized and some of them displayed good antifungal activities against G. zeae, F. oxysporum and C. mandshurica in preliminary antifungal activity tests. Full article
Open AccessArticle Adding Chemical Cross-Links to a Physical Hydrogel
Molecules 2009, 14(9), 3662-3675; https://doi.org/10.3390/molecules14093662
Received: 30 June 2009 / Revised: 27 August 2009 / Accepted: 16 September 2009 / Published: 17 September 2009
Cited by 7 | Viewed by 8187 | PDF Full-text (711 KB)
Abstract
Synergistic hydrogels are often encountered in polysaccharide mixtures widely used in food and biopharma products. The xanthan and konjac glucomannan pair provides one of the most studied synergistic hydrogels. Recently we showed that the junction zones stabilizing the 3D structure of this gel
[...] Read more.
Synergistic hydrogels are often encountered in polysaccharide mixtures widely used in food and biopharma products. The xanthan and konjac glucomannan pair provides one of the most studied synergistic hydrogels. Recently we showed that the junction zones stabilizing the 3D structure of this gel are present as macromolecular complexes in solution formed by the partially depolymerised polysaccharidic chains. The non-covalent interactions stabilizing the structure of the polysaccharidic complex cause the melting of the ordered structure of the complex in the solution and of the hydrogels. Introduction of chemical cross-links in the 3D structure of the synergistic hydrogel removes this behaviour, adding new features to the swelling and to the viscoelastic properties of the cured hydrogel. The use of epichlorohydrin as low molecular weight cross-linker does not impact unfavourably on the viability of NIH 3T3 fibroblasts. Full article
(This article belongs to the Special Issue Macromolecules Applied to Pharmaceutics)
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Open AccessReview Medicinal Chemistry of Annonaceous Acetogenins: Design, Synthesis, and Biological Evaluation of Novel Analogues
Molecules 2009, 14(9), 3621-3661; https://doi.org/10.3390/molecules14093621
Received: 4 August 2009 / Revised: 31 August 2009 / Accepted: 11 September 2009 / Published: 17 September 2009
Cited by 66 | Viewed by 13049 | PDF Full-text (2839 KB)
Abstract
Most Annonaceous acetogenins are characterized by between one and three THF ring(s) with one or two flanking hydroxyl group(s) in the center of a C32/34 fatty acid, and the terminal carboxylic acid is combined with a 2-propanol unit to form an α,β-unsaturated γ-lactone.
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Most Annonaceous acetogenins are characterized by between one and three THF ring(s) with one or two flanking hydroxyl group(s) in the center of a C32/34 fatty acid, and the terminal carboxylic acid is combined with a 2-propanol unit to form an α,β-unsaturated γ-lactone. While many studies have addressed the properties and synthesis of natural acetogenins due to their attractive biological activities and unique structural features, a number of analogues have also been described. This review covers the design, synthesis, and biological evaluation of acetogenin analogues. Full article
(This article belongs to the Special Issue Acetogenins: Extraction, Synthesis and Biological Properties)
Open AccessArticle Microwave-Assisted Synthesis and Crystal Structure of Oxo(diperoxo)(4,4'-di-tert-butyl-2,2'-bipyridine)-molybdenum(VI)
Molecules 2009, 14(9), 3610-3620; https://doi.org/10.3390/molecules14093610
Received: 21 July 2009 / Revised: 3 September 2009 / Accepted: 14 September 2009 / Published: 16 September 2009
Cited by 17 | Viewed by 10993 | PDF Full-text (438 KB)
Abstract
The oxodiperoxo complex MoO(O2)2(tbbpy) (tbbpy = 4,4'-di-tert-butyl-2,2'- bipyridine) was isolated from the reaction of MoO2Cl2(tbbpy) in water under microwaveassisted heating at 120 ºC for 4 h. The structure of the oxodiperoxo complex was
[...] Read more.
The oxodiperoxo complex MoO(O2)2(tbbpy) (tbbpy = 4,4'-di-tert-butyl-2,2'- bipyridine) was isolated from the reaction of MoO2Cl2(tbbpy) in water under microwaveassisted heating at 120 ºC for 4 h. The structure of the oxodiperoxo complex was determined by single crystal X-ray diffraction. The MoVI centre is seven-coordinated with a geometry which strongly resembles a highly distorted bipyramid. Individual MoO(O2)2(tbbpy) complexes are interdigitated along the [010] direction to form a column. The crystal structure is formed by the close packing of the columnar-stacked complexes. Interactions between neighbouring columns are essentially of van der Waals type mediated by the need to effectively fill the available space. Full article
(This article belongs to the Special Issue Microwave Assisted Synthesis)
Open AccessArticle Synthesis of a [2.2.2] Cryptand Containing Reactive Functional Groups
Molecules 2009, 14(9), 3600-3609; https://doi.org/10.3390/molecules14093600
Received: 10 August 2009 / Revised: 3 September 2009 / Accepted: 14 September 2009 / Published: 15 September 2009
Cited by 2 | Viewed by 6106 | PDF Full-text (398 KB)
Abstract
The functional group-containing potassium ionophore 195,245-dibromo-4,7,13,16,20,23-hexaoxa-1,10-diaza-19(1,2),24(1,2)-dibenzabicyclo[8.8.6]tetracosaphane has been synthesized. Full article
Open AccessArticle Development of a High-Throughput Assay for Screening of γ-Secretase Inhibitor with Endogenous Human, Mouse or Drosophila γ-Secretase
Molecules 2009, 14(9), 3589-3599; https://doi.org/10.3390/molecules14093589
Received: 30 July 2009 / Revised: 22 August 2009 / Accepted: 31 August 2009 / Published: 14 September 2009
Cited by 9 | Viewed by 6939 | PDF Full-text (424 KB)
Abstract
Selective lowering of amyloid-β levels with small-molecule γ-secretase inhibitors is a promising therapeutic approach for Alzheimer’s disease. In this work, we developed a high throughput assay for screening of γ-secretase inhibitors with endogenous γ-secretase and a fluorogenic substrate. The IC50 values of
[...] Read more.
Selective lowering of amyloid-β levels with small-molecule γ-secretase inhibitors is a promising therapeutic approach for Alzheimer’s disease. In this work, we developed a high throughput assay for screening of γ-secretase inhibitors with endogenous γ-secretase and a fluorogenic substrate. The IC50 values of known γ-secretase inhibitors generated with this method were comparable with reported values obtained by other methods. The assay was optimized and applied to a small-scale screening of 1,280 compounds. The discovery of several new inhibitors warrants further investigation. This assay was also proven to be easily adopted to test compounds for drosophila and mouse γ-secretase, which could be very useful to assess compounds activity against γ-secretase from different species before the in vivo test in animal models. Full article
Open AccessReview Chemistry of the M (M=Fe, Ca, Ba)-Se-H2O Systems at 25 °C
Molecules 2009, 14(9), 3567-3588; https://doi.org/10.3390/molecules14093567
Received: 28 July 2009 / Revised: 18 August 2009 / Accepted: 11 September 2009 / Published: 14 September 2009
Cited by 8 | Viewed by 7970 | PDF Full-text (856 KB)
Abstract
The chemistry of the M (M=Fe, Ca, Ba)-Se-H2O systems at 25 °C is reviewed based on our previous papers. In this paper, the phase equilibria in the Fe(III)-Se(IV)-H2O, Ca-Se(IV,VI)-H2O and Ba-Se(IV,VI)-H2O systems at 25 °C
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The chemistry of the M (M=Fe, Ca, Ba)-Se-H2O systems at 25 °C is reviewed based on our previous papers. In this paper, the phase equilibria in the Fe(III)-Se(IV)-H2O, Ca-Se(IV,VI)-H2O and Ba-Se(IV,VI)-H2O systems at 25 °C are discussed. Then, the three-stage process for removal of selenium from industrial waste water [Se(IV,VI) < 1,500 mg/L] containing sulfuric acid was introduced. This seems to be a promising process for selenium removal from acidic sulfate waste water containing high concentration levels of selenium to below 0.1 mg/L. Full article
(This article belongs to the Special Issue Selenium and Tellurium Chemistry)
Open AccessArticle Microwave-Assisted Solvent-Free Acetylation of Cellulose with Acetic Anhydride in the Presence of Iodine as a Catalyst
Molecules 2009, 14(9), 3551-3566; https://doi.org/10.3390/molecules14093551
Received: 16 July 2009 / Revised: 9 September 2009 / Accepted: 11 September 2009 / Published: 11 September 2009
Cited by 65 | Viewed by 11189 | PDF Full-text (270 KB)
Abstract
In this work an optimization of the solvent-free acetylation of cellulose with acetic anhydride under microwave heating with iodine as a catalyst was performed. The optimized parameters included the microwave irradiation power from 300 W to 800 W, the reaction time between 5
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In this work an optimization of the solvent-free acetylation of cellulose with acetic anhydride under microwave heating with iodine as a catalyst was performed. The optimized parameters included the microwave irradiation power from 300 W to 800 W, the reaction time between 5 to 40 min, the reaction temperature from 80 to 130 °C, and the amount of iodine from 1 to 15 mol%. The extent of the acetylation was measured by yield and the degree of substitution (DS), which was determined by a back-titration method. Acetylated cellulose was characterized by FT-IR, CP/MAS 13C-NMR, WRXD, and thermogravimetric analysis. The results showed that within the range of catalyst amounts studied, the DS increased as the amount of iodine used increased, however, it was barely affected by microwave output. It was also found that the reaction time and temperature had an active influence on the extent of acetylation, however, this did not mean that at the higher temperature a better acetylation of cellulose would be obtained. The optimal reaction time and temperature found in this work were 30 min and 130 °C. Full article
(This article belongs to the Special Issue Microwave Assisted Synthesis)
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Open AccessArticle Electrochemical Reduction of Coumarins at a Film-Modified Electrode and Determination of Their Levels in Essential Oils and Traditional Chinese Herbal Medicines
Molecules 2009, 14(9), 3538-3550; https://doi.org/10.3390/molecules14093538
Received: 22 June 2009 / Revised: 26 August 2009 / Accepted: 9 September 2009 / Published: 11 September 2009
Cited by 11 | Viewed by 6284 | PDF Full-text (199 KB)
Abstract
The electrochemical reduction of coumarins on glassy carbon and electrodeposited metal electrodes was investigated in a Britton-Robinson buffer (pH 1.87-11.98). The effects of various factors, such as the deposition material, time, and concentration of mercury, on the precision of the analysis were explored.
[...] Read more.
The electrochemical reduction of coumarins on glassy carbon and electrodeposited metal electrodes was investigated in a Britton-Robinson buffer (pH 1.87-11.98). The effects of various factors, such as the deposition material, time, and concentration of mercury, on the precision of the analysis were explored. The possible reaction mechanism of the reduction process with regards to scan rates, peak potentials, and currents is discussed. Electroreduction was used to quantitatively determine the levels of coumarins in some essential oils and traditional Chinese herbal medicines. A comparison with high performance liquid chromatography analysis results shows good agreement. Full article
(This article belongs to the Special Issue Coumarins and Xanthones)
Open AccessArticle Ruthenium(III) Chloride Catalyzed Acylation of Alcohols, Phenols, and Thiols in Room Temperature Ionic Liquids
Molecules 2009, 14(9), 3528-3537; https://doi.org/10.3390/molecules14093528
Received: 3 July 2009 / Revised: 10 September 2009 / Accepted: 10 September 2009 / Published: 10 September 2009
Cited by 18 | Viewed by 8741 | PDF Full-text (180 KB)
Abstract
Ruthenium(III) chloride-catalyzed acylation of a variety of alcohols, phenols, and thiols was achieved in high yields under mild conditions (room temperature) in the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]). The ionic liquid and ruthenium catalyst can be recycled at least 10 times.
[...] Read more.
Ruthenium(III) chloride-catalyzed acylation of a variety of alcohols, phenols, and thiols was achieved in high yields under mild conditions (room temperature) in the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]). The ionic liquid and ruthenium catalyst can be recycled at least 10 times. Our system not only solves the basic problem of ruthenium catalyst reuse, but also avoids the use of volatile acetonitrile as solvent. Full article
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Open AccessReview Mouse Models Targeting Selenocysteine tRNA Expression for Elucidating the Role of Selenoproteins in Health and Development
Molecules 2009, 14(9), 3509-3527; https://doi.org/10.3390/molecules14093509
Received: 17 August 2009 / Revised: 3 September 2009 / Accepted: 7 September 2009 / Published: 10 September 2009
Cited by 24 | Viewed by 10150 | PDF Full-text (328 KB)
Abstract
Selenium (Se) deficiency has been known for many years to be associated with disease, impaired growth and a variety of other metabolic disorders in mammals. Only recently has the major role that Se-containing proteins, designated selenoproteins, play in many aspects of health and
[...] Read more.
Selenium (Se) deficiency has been known for many years to be associated with disease, impaired growth and a variety of other metabolic disorders in mammals. Only recently has the major role that Se-containing proteins, designated selenoproteins, play in many aspects of health and development begun to emerge. Se is incorporated into protein by way of the Se-containing amino acid, selenocysteine (Sec). The synthesis of selenoproteins is dependent on Sec tRNA for insertion of Sec, the 21st amino acid in the genetic code, into protein. We have taken advantage of this dependency to modulate the expression of Sec tRNA that in turn modulates the expression of selenoproteins by generating transgenic, conditional knockout, transgenic/standard knockout and transgenic/conditional knockout mouse models, all of which involve the Sec tRNA gene, to elucidate the intracellular roles of this protein class. Full article
(This article belongs to the Special Issue Selenium and Tellurium Chemistry)
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Open AccessArticle Synthesis and Cytotoxicity of Novel Hexahydrothienocycloheptapyridazinone Derivatives
Molecules 2009, 14(9), 3494-3508; https://doi.org/10.3390/molecules14093494
Received: 17 July 2009 / Revised: 26 August 2009 / Accepted: 9 September 2009 / Published: 9 September 2009
Cited by 9 | Viewed by 6639 | PDF Full-text (332 KB)
Abstract
Designed as a new group of tricyclic molecules containing the thienocycloheptapyridazinone ring system, a number of 2N-substituted-hexahydrothienocycloheptapyridazinone derivatives were synthesized and their biological activity evaluated. Among the synthesized compounds, derivatives 7d and 7h were found to possess cytotoxic activity against non-small
[...] Read more.
Designed as a new group of tricyclic molecules containing the thienocycloheptapyridazinone ring system, a number of 2N-substituted-hexahydrothienocycloheptapyridazinone derivatives were synthesized and their biological activity evaluated. Among the synthesized compounds, derivatives 7d and 7h were found to possess cytotoxic activity against non-small cell lung cancer and central nervous system cancer cell lines, respectively. Full article
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Open AccessCommunication Physicochemical Properties and Antioxidant Activities of Luteolin-Phospholipid Complex
Molecules 2009, 14(9), 3486-3493; https://doi.org/10.3390/molecules14093486
Received: 10 July 2009 / Revised: 12 August 2009 / Accepted: 24 August 2009 / Published: 9 September 2009
Cited by 39 | Viewed by 8087 | PDF Full-text (246 KB)
Abstract
luteolin and phospholipid complex was prepared to improve the lipophilic properties of luteolin. The physicochemical properties of the complex were analyzed by ultraviolet-visible spectrometry (UV), infrared spectrometry (IR), X-ray diffractometry (XRD) and differential scanning calorimetry (DSC). The results showed that luteolin and phospholipid
[...] Read more.
luteolin and phospholipid complex was prepared to improve the lipophilic properties of luteolin. The physicochemical properties of the complex were analyzed by ultraviolet-visible spectrometry (UV), infrared spectrometry (IR), X-ray diffractometry (XRD) and differential scanning calorimetry (DSC). The results showed that luteolin and phospholipid in the complex were joined by non-covalent-bonds and did not form a new compound. It was found that the complex was an effective scavenger of DPPH radicals, with an IC50 value of 28.33 μg/mL. In the Rancimat antioxidant test using lard oil as substrate, the complex also showed the strong antioxidant activity. Full article
Open AccessReview The Vitamin Nicotinamide: Translating Nutrition into Clinical Care
Molecules 2009, 14(9), 3446-3485; https://doi.org/10.3390/molecules14093446
Received: 17 August 2009 / Revised: 8 September 2009 / Accepted: 8 September 2009 / Published: 9 September 2009
Cited by 122 | Viewed by 10854 | PDF Full-text (790 KB)
Abstract
Nicotinamide, the amide form of vitamin B3 (niacin), is changed to its mononucleotide compound with the enzyme nicotinic acide/nicotinamide adenylyltransferase, and participates in the cellular energy metabolism that directly impacts normal physiology. However, nicotinamide also influences oxidative stress and modulates multiple pathways
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Nicotinamide, the amide form of vitamin B3 (niacin), is changed to its mononucleotide compound with the enzyme nicotinic acide/nicotinamide adenylyltransferase, and participates in the cellular energy metabolism that directly impacts normal physiology. However, nicotinamide also influences oxidative stress and modulates multiple pathways tied to both cellular survival and death. During disorders that include immune system dysfunction, diabetes, and aging-related diseases, nicotinamide is a robust cytoprotectant that blocks cellular inflammatory cell activation, early apoptotic phosphatidylserine exposure, and late nuclear DNA degradation. Nicotinamide relies upon unique cellular pathways that involve forkhead transcription factors, sirtuins, protein kinase B (Akt), Bad, caspases, and poly (ADP-ribose) polymerase that may offer a fine line with determining cellular longevity, cell survival, and unwanted cancer progression. If one is cognizant of the these considerations, it becomes evident that nicotinamide holds great potential for multiple disease entities, but the development of new therapeutic strategies rests heavily upon the elucidation of the novel cellular pathways that nicotinamide closely governs. Full article
(This article belongs to the Special Issue Vitamins)
Open AccessArticle The Use of MoStBioDat for Rapid Screening of Molecular Diversity
Molecules 2009, 14(9), 3436-3445; https://doi.org/10.3390/molecules14093436
Received: 24 July 2009 / Revised: 10 August 2009 / Accepted: 3 September 2009 / Published: 8 September 2009
Cited by 6 | Viewed by 6971 | PDF Full-text (164 KB)
Abstract
MoStBioDat is a uniform data storage and extraction system with an extensive array of tools for structural similarity measures and pattern matching which is essential to facilitate the drug discovery process. Structure-based database screening has recently become a common and efficient technique in
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MoStBioDat is a uniform data storage and extraction system with an extensive array of tools for structural similarity measures and pattern matching which is essential to facilitate the drug discovery process. Structure-based database screening has recently become a common and efficient technique in early stages of the drug development, shifting the emphasis from rational drug design into the probability domain of more or less random discovery. The virtual ligand screening (VLS), an approach based on high-throughput flexible docking, samples a virtually infinite molecular diversity of chemical libraries increasing the concentration of molecules with high binding affinity. The rapid process of subsequent examination of a large number of molecules in order to optimize the molecular diversity is an attractive alternative to the traditional methods of lead discovery. This paper presents the application of the MoStBioDat package not only as a data management platform but mainly in substructure searching. In particular, examples of the applications of MoStBioDat are discussed and analyzed. Full article
(This article belongs to the Special Issue Combinatorial Chemistry)
Open AccessArticle Microbial Growth and Quorum Sensing Antagonist Activities of Herbal Plants Extracts
Molecules 2009, 14(9), 3425-3435; https://doi.org/10.3390/molecules14093425
Received: 2 July 2009 / Revised: 26 July 2009 / Accepted: 5 August 2009 / Published: 3 September 2009
Cited by 60 | Viewed by 8888 | PDF Full-text (74 KB)
Abstract
Antimicrobial and antiquorum sensing (AQS) activities of fourteen ethanolic extracts of different parts of eight plants were screened against four Gram-positive, five Gram-negative bacteria and four fungi. Depending on the plant part extract used and the test microorganism, variable activities were recorded at
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Antimicrobial and antiquorum sensing (AQS) activities of fourteen ethanolic extracts of different parts of eight plants were screened against four Gram-positive, five Gram-negative bacteria and four fungi. Depending on the plant part extract used and the test microorganism, variable activities were recorded at 3 mg per disc. Among the Grampositive bacteria tested, for example, activities of Laurus nobilis bark extract ranged between a 9.5 mm inhibition zone against Bacillus subtilis up to a 25 mm one against methicillin resistant Staphylococcus aureus. Staphylococcus aureus and Aspergillus fumigatus were the most susceptible among bacteria and fungi tested towards other plant parts. Of interest is the tangible antifungal activity of a Tecoma capensis flower extract, which is reported for the first time. However, minimum inhibitory concentrations (MIC's) for both bacteria and fungi were relatively high (0.5-3.0 mg). As for antiquorum sensing activity against Chromobacterium violaceum, superior activity (>17 mm QS inhibition) was associated with Sonchus oleraceus and Laurus nobilis extracts and weak to good activity (8-17 mm) was recorded for other plants. In conclusion, results indicate the potential of these plant extracts in treating microbial infections through cell growth inhibition or quorum sensing antagonism, which is reported for the first time, thus validating their medicinal use. Full article
Open AccessArticle Fast and Green Microwave-Assisted Conversion of Essential Oil Allylbenzenes into the Corresponding Aldehydes via Alkene Isomerization and Subsequent Potassium Permanganate Promoted Oxidative Alkene Group Cleavage
Molecules 2009, 14(9), 3411-3424; https://doi.org/10.3390/molecules14093411
Received: 12 August 2009 / Revised: 2 September 2009 / Accepted: 2 September 2009 / Published: 3 September 2009
Cited by 23 | Viewed by 10650 | PDF Full-text (324 KB)
Abstract
Essential oil allylbenzenes from have been converted quickly and efficiently into the corresponding benzaldehydes in good yields by a two-step “green” reaction pathway based on a solventless alkene group isomerization by KF/Al2O3 to form the corresponding 1-arylpropene and a subsequent
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Essential oil allylbenzenes from have been converted quickly and efficiently into the corresponding benzaldehydes in good yields by a two-step “green” reaction pathway based on a solventless alkene group isomerization by KF/Al2O3 to form the corresponding 1-arylpropene and a subsequent solventless oxidation of the latter to the corresponding benzaldehyde by KMnO4/CuSO4·5H2O. The assistance by microwave irradiation results in very short reaction times (<15 minutes). The green conversion of eugenol (4-allyl-2-methoxyphenol) into vanillin (4-hydroxy-3-methoxybenzaldehyde) has been carried out in a similar way, requiring however two additional microwave-assisted synthetic steps for acetylation of the hydroxy group prior to the oxidation reaction, and for the final deacetylation of vanillin acetate (4-acetoxy-3-methoxybenzaldehyde) by KF/Al2O3 under solvent-free conditions, respectively. Full article
(This article belongs to the Special Issue Microwave Assisted Synthesis)
Open AccessArticle Identification of a Benzamide Derivative that Inhibits Stress-Induced Adrenal Corticosteroid Synthesis
Molecules 2009, 14(9), 3392-3410; https://doi.org/10.3390/molecules14093392
Received: 27 July 2009 / Revised: 14 August 2009 / Accepted: 1 September 2009 / Published: 3 September 2009
Cited by 1 | Viewed by 8337 | PDF Full-text (278 KB)
Abstract
Elevated serum glucocorticoid levels contribute to the progression of many diseases, including depression, Alzheimer’s disease, hypertension, and acquired immunodeficiency syndrome. Here we show that the benzamide derivative N-[2-(4-cyclopropanecarbonyl-3-methyl-piperazin-1-yl)-1-(tert-butyl-1H-indol-3-yl-methyl)-2-oxo-ethyl]-4-nitrobenzamide (SP-10) inhibits dibutyryl cyclic AMP (dbcAMP)-induced corticosteroid synthesis in a
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Elevated serum glucocorticoid levels contribute to the progression of many diseases, including depression, Alzheimer’s disease, hypertension, and acquired immunodeficiency syndrome. Here we show that the benzamide derivative N-[2-(4-cyclopropanecarbonyl-3-methyl-piperazin-1-yl)-1-(tert-butyl-1H-indol-3-yl-methyl)-2-oxo-ethyl]-4-nitrobenzamide (SP-10) inhibits dibutyryl cyclic AMP (dbcAMP)-induced corticosteroid synthesis in a dose-dependent manner in Y-1 adrenal cortical mouse tumor cells, without affecting basal steroid synthesis and reduced stress-induced corticosterone increases in rats without affecting the physiological levels of the steroid in blood. SP-10 did not affect cholesterol transport and metabolism by the mitochondria but was unexpectedly found to increase 3-hydroxy-3-methylglutaryl-coenzyme A, low density lipoprotein receptor, and scavenger receptor class B type I (SR-BI) expression. However, it also markedly reduced dbcAMP-induced NBD-cholesterol uptake, suggesting that this is a compensatory mechanism aimed at maintaining cholesterol levels. SP-10 also induced a redistribution of filamentous (F-) and monomeric (G-) actin, leading to decreased actin levels in the submembrane cytoskeleton suggesting that SP-10-induced changes in actin distribution might prevent the formation of microvilli–cellular structures required for SRBI-mediated cholesterol uptake in adrenal cells. Full article
(This article belongs to the Special Issue Neuroprotective Strategies)
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Open AccessArticle Preparation and Characterization of Novel Gellan Gum Hydrogels Suitable for Modified Drug Release
Molecules 2009, 14(9), 3376-3391; https://doi.org/10.3390/molecules14093376
Received: 26 June 2009 / Revised: 30 July 2009 / Accepted: 31 August 2009 / Published: 3 September 2009
Cited by 51 | Viewed by 9152 | PDF Full-text (476 KB)
Abstract
Innovative hydrogels obtained by physical and chemical crosslinking of deacylated Gellan gum have been characterized in terms of water uptake, rheological properties and compressibility, and the behaviour of the tested materials, according to the type of the obtained network, is thoroughly discussed. The
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Innovative hydrogels obtained by physical and chemical crosslinking of deacylated Gellan gum have been characterized in terms of water uptake, rheological properties and compressibility, and the behaviour of the tested materials, according to the type of the obtained network, is thoroughly discussed. The release from the various gels of loaded model molecules of different steric hindrance was also investigated and the trend of the release profiles has been related to the structures proposed for the physical and the chemical hydrogel. Full article
(This article belongs to the Special Issue Macromolecules Applied to Pharmaceutics)
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Open AccessCommunication Cesium Carbonate-Catalyzed α-Phenylchalcogenation of Carbonyl Compounds with Diphenyl Dichalcogenide
Molecules 2009, 14(9), 3367-3375; https://doi.org/10.3390/molecules14093367
Received: 31 July 2009 / Revised: 26 August 2009 / Accepted: 2 September 2009 / Published: 2 September 2009
Cited by 6 | Viewed by 5752 | PDF Full-text (247 KB)
Abstract
It was found that cesium carbonate has a unique catalytic ability on the reaction of carbonyl compounds with diphenyl diselenide to give the corresponding α-phenylseleno carbonyl compounds in moderate to good yields. Similarly, the α-phenylthiolation of carbonyl compounds with diphenyl disulfide was promoted
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It was found that cesium carbonate has a unique catalytic ability on the reaction of carbonyl compounds with diphenyl diselenide to give the corresponding α-phenylseleno carbonyl compounds in moderate to good yields. Similarly, the α-phenylthiolation of carbonyl compounds with diphenyl disulfide was promoted by the cesium carbonate catalyst. Full article
(This article belongs to the Special Issue Selenium and Tellurium Chemistry)
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Open AccessArticle A New 4α-Methylated Sterol from a Nephthea sp. (Nephtheidae) Bornean Soft Coral
Molecules 2009, 14(9), 3360-3366; https://doi.org/10.3390/molecules14093360
Received: 20 July 2009 / Revised: 17 August 2009 / Accepted: 19 August 2009 / Published: 2 September 2009
Cited by 12 | Viewed by 5482 | PDF Full-text (166 KB)
Abstract
A new 4α-methyl sterol, 4α-methyl-ergosta-6,8(14),22E-triene-3β-ol (1), was isolated along with cholesterol from a Nephthea sp. Bornean soft coral The structure of compound 1 was elucidated on the basis of spectroscopic analysis and comparison of the data with those of the related compounds. Full article
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