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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 | 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 | 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 249 | 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 68 | 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
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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 16 | 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 | 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 | 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
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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 | 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,
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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 | 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
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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 | 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 | 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
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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 64 | 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 | 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
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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 | 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 8 | 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
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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
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