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Molecules, Volume 15, Issue 3 (March 2010), Pages 1097-2059

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Open AccessArticle Cationic Heteroleptic Cyclometalated IridiumIII Complexes Containing Phenyl-Triazole and Triazole-Pyridine Clicked Ligands
Molecules 2010, 15(3), 2039-2059; https://doi.org/10.3390/molecules15032039
Received: 8 February 2010 / Revised: 8 March 2010 / Accepted: 18 March 2010 / Published: 23 March 2010
Cited by 58 | PDF Full-text (815 KB) | Supplementary Files
Abstract
Novel heteroleptic iridium complexes containing the 1-substituted-4-phenyl-1H-1,2,3-triazole (phtl) cyclometalating ligand have been synthesized. The 3+2 Huisgen dipolar cycloaddition method (‘click’ chemistry) was utilized to prepare a class of bidentate ligands (phtl) bearing different substituents on the triazole moiety. By using various
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Novel heteroleptic iridium complexes containing the 1-substituted-4-phenyl-1H-1,2,3-triazole (phtl) cyclometalating ligand have been synthesized. The 3+2 Huisgen dipolar cycloaddition method (‘click’ chemistry) was utilized to prepare a class of bidentate ligands (phtl) bearing different substituents on the triazole moiety. By using various ligands (phtl-R1 and pytl-R2) (R1=adamantane, methyl and R2=adamantane, methyl, β-cyclodextrin, ursodeoxycholic acid), we prepared a small library of new luminescent ionic iridium complexes [Ir(phtr-R1)2(pytl-R2)]Cl and report on their photophysical properties. The flexibility of the clicking approach allows a straightforward control on the chemical-physical properties of the complexes by varying the nature of the substituent on the ligand. Full article
(This article belongs to the Special Issue Click Chemistry)
Open AccessArticle Acetamide Derivatives with Antioxidant Activity and Potential Anti-Inflammatory Activity
Molecules 2010, 15(3), 2028-2038; https://doi.org/10.3390/molecules15032028
Received: 2 February 2010 / Revised: 9 March 2010 / Accepted: 18 March 2010 / Published: 23 March 2010
Cited by 28 | PDF Full-text (235 KB)
Abstract
This study reports the synthesis and antioxidant activity of some new acetamide derivatives. The compounds’ structures were elucidated by NMR analysis and their melting points were measured. The in vitro antioxidant activity of these compounds was tested by evaluating the amount of scavenged
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This study reports the synthesis and antioxidant activity of some new acetamide derivatives. The compounds’ structures were elucidated by NMR analysis and their melting points were measured. The in vitro antioxidant activity of these compounds was tested by evaluating the amount of scavenged ABTS radical and estimating ROS and NO production in tBOH- or LPS-stimulated J774.A1 macrophages. All compounds were tested for their effect on cell viability by an MTT assay and by a Brine Shrimp Test. Full article
Open AccessArticle Antioxidant Capacities and Phenolic Levels of Different Varieties of Serbian White Wines
Molecules 2010, 15(3), 2016-2027; https://doi.org/10.3390/molecules15032016
Received: 22 January 2010 / Revised: 23 February 2010 / Accepted: 9 March 2010 / Published: 22 March 2010
Cited by 26 | PDF Full-text (376 KB)
Abstract
The biologically active compounds in wine, especially phenolics, are responsible for reduced risk of developing chronic diseases (cardiovascular disrease, cancer, diabetes, etc.), due to their antioxidant activities. We determined the contents of total phenolics (TP) and total flavonoids (TF) in selected Serbian
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The biologically active compounds in wine, especially phenolics, are responsible for reduced risk of developing chronic diseases (cardiovascular disrease, cancer, diabetes, etc.), due to their antioxidant activities. We determined the contents of total phenolics (TP) and total flavonoids (TF) in selected Serbian white wines by colorimetric methods. Total antioxidant activity (TAA) of the white wines was analyzed using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging capacity assay. Međaš beli had the highest content of TP, TF and TAA. The radical scavenging capacity (RSC) and total antioxidant activity (TAA) of white wines were 15.30% and 1.055 mM Trolox equivalent, respectively. Total phenolic (TP) and total flavonoid (TF) contents in white wines ranged from 238.3 to 420.6 mg gallic acid equivalent per L of wines and 42.64 to 81.32 mg catechin equivalent per L of wines, respectively. A high and significant correlation between antioxidant activity and total phenolic content was determined in wines (R2 = 0.968, p < 0.01). For the individual polyphenols determination we used a high performance liquid chromatography (HPLC)-diode array detection (DAD) technique. The majority of white wine polyphenols was represent by four hydroxycinnamic acids (HCAs). Full article
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Open AccessArticle The Combination of TRAIL and Isoflavones Enhances Apoptosis in Cancer Cells
Molecules 2010, 15(3), 2000-2015; https://doi.org/10.3390/molecules15032000
Received: 4 February 2010 / Revised: 9 March 2010 / Accepted: 19 March 2010 / Published: 22 March 2010
Cited by 32 | PDF Full-text (204 KB)
Abstract
Isoflavones are a class of bioactive polyphenols with cancer chemopreventive properties. TRAIL (tumor necrosis factor-related apoptosis-inducing ligand) is a naturally occurring antitumor agent that selectively induces programmed death (apoptosis) in cancer cells. Polyphenols can modulate TRAIL-mediated apoptosis in cancer cells. We examined the
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Isoflavones are a class of bioactive polyphenols with cancer chemopreventive properties. TRAIL (tumor necrosis factor-related apoptosis-inducing ligand) is a naturally occurring antitumor agent that selectively induces programmed death (apoptosis) in cancer cells. Polyphenols can modulate TRAIL-mediated apoptosis in cancer cells. We examined the cytotoxic and apoptotic activities of isoflavones in combination with TRAIL on HeLa cancer cells. The apoptosis was detected by fluorescence microscopy with annexin V-FITC. The cytotoxicity was evaluated by MTT and LDH assays. The tested isoflavones: genistein, biochanin-A and neobavaisoflavone enhance TRAIL-induced apoptosis in HeLa cells. Our study indicated that isoflavones augmented TRAIL-cytotoxicity against cancer cells and confirmed potential role of those polyphenols in chemoprevention. Full article
Open AccessReview QSAR Models for Reproductive Toxicity and Endocrine Disruption Activity
Molecules 2010, 15(3), 1987-1999; https://doi.org/10.3390/molecules15031987
Received: 21 December 2009 / Revised: 29 January 2010 / Accepted: 19 March 2010 / Published: 22 March 2010
Cited by 20 | PDF Full-text (285 KB)
Abstract
Reproductive toxicity is an important regulatory endpoint, which is required in registration procedures of chemicals used for different purposes (for example pesticides). The in vivo tests are expensive, time consuming and require large numbers of animals, which must be sacrificed. Therefore an effort
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Reproductive toxicity is an important regulatory endpoint, which is required in registration procedures of chemicals used for different purposes (for example pesticides). The in vivo tests are expensive, time consuming and require large numbers of animals, which must be sacrificed. Therefore an effort is ongoing to develop alternative In vitro and in silico methods to evaluate reproductive toxicity. In this review we describe some modeling approaches. In the first example we describe the CAESAR model for prediction of reproductive toxicity; the second example shows a classification model for endocrine disruption potential based on counter propagation artificial neural networks; the third example shows a modeling of relative binding affinity to rat estrogen receptor, and the fourth one shows a receptor dependent modeling experiment. Full article
(This article belongs to the Special Issue Molecular Diversity Feature Papers)
Open AccessAddendum Addendum: De Sousa Luis, J.A., et al. Synthesis of New Imidazolidin-2,4-dione and 2-Thioxo-imidazolidin-4-ones via C-Phenylglycine Derivatives. Molecules 2010, 15, 128-137
Molecules 2010, 15(3), 1985-1986; https://doi.org/10.3390/molecules15031985
Received: 12 February 2010 / Published: 22 March 2010
PDF Full-text (26 KB)
Abstract
The authors wish to make the following correction to their paper [1], published recently in Molecules. The coauthor RalineMendonça dos Anjos was omitted from the author list, which should read as follows: [...] Full article
Open AccessArticle Conjugate Addition of Nucleophiles to the Vinyl Function of 2-Chloro-4-vinylpyrimidine Derivatives
Molecules 2010, 15(3), 1973-1984; https://doi.org/10.3390/molecules15031973
Received: 2 March 2010 / Revised: 9 March 2010 / Accepted: 18 March 2010 / Published: 19 March 2010
Cited by 5 | PDF Full-text (171 KB)
Abstract
Conjugate addition reaction of various nucleophiles across the vinyl group of 2-chloro-4-vinylpyrimidine, 2-chloro-4-(1-phenylvinyl)pyrimidine and 2-chloro-4-vinylquinazoline provides the corresponding 2-chloro-4-(2-substituted ethyl)pyrimidines and 2-chloro-4-(2-substituted ethyl)quinazolines. Treatment of these products, without isolation, with N-methylpiperazine results in nucleophilic displacement of chloride and yields the corresponding 2,4-disubstituted
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Conjugate addition reaction of various nucleophiles across the vinyl group of 2-chloro-4-vinylpyrimidine, 2-chloro-4-(1-phenylvinyl)pyrimidine and 2-chloro-4-vinylquinazoline provides the corresponding 2-chloro-4-(2-substituted ethyl)pyrimidines and 2-chloro-4-(2-substituted ethyl)quinazolines. Treatment of these products, without isolation, with N-methylpiperazine results in nucleophilic displacement of chloride and yields the corresponding 2,4-disubstituted pyrimidines and quinazolines. Full article
Open AccessCommunication Preparation of the Pyridinium Salts Differing in the Length of the N-Alkyl Substituent
Molecules 2010, 15(3), 1967-1972; https://doi.org/10.3390/molecules15031967
Received: 14 December 2009 / Revised: 4 March 2010 / Accepted: 10 March 2010 / Published: 19 March 2010
Cited by 15 | PDF Full-text (99 KB)
Abstract
Quaternary pyridinium salts with chains ranging from C8 to C20 belong in the large group of cationic surfactants. In this paper, the preparation of such cationic surface active agents based on the pyridinium moiety and differing in the length of the
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Quaternary pyridinium salts with chains ranging from C8 to C20 belong in the large group of cationic surfactants. In this paper, the preparation of such cationic surface active agents based on the pyridinium moiety and differing in the length of the N-alkyl chain is described. Additionally, HPLC technique was established to distinguish each prepared pyridinium analogue. This study represents universal method for preparation and identification of quaternary pyridinium detergents. Full article
Open AccessArticle New Cytotoxic Azaphilones from Monascus purpureus-Fermented Rice (Red Yeast Rice)
Molecules 2010, 15(3), 1958-1966; https://doi.org/10.3390/molecules15031958
Received: 18 January 2010 / Revised: 1 March 2010 / Accepted: 8 March 2010 / Published: 18 March 2010
Cited by 23 | PDF Full-text (157 KB) | Supplementary Files
Abstract
Using a cell-based cytotoxicity assay three new cytotoxic azaphilones, including two stereoisomers and designated monapurones A-C (1-3), were isolated from the extract of Monascus purpureus-fermented rice (red yeast rice). Their structures were elucidated by detailed interpretation of spectroscopic and
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Using a cell-based cytotoxicity assay three new cytotoxic azaphilones, including two stereoisomers and designated monapurones A-C (1-3), were isolated from the extract of Monascus purpureus-fermented rice (red yeast rice). Their structures were elucidated by detailed interpretation of spectroscopic and chemical data. The relative configurations were assigned on the basis of analysis of NOE data, and the absolute configurations were determined by direct comparison of their CD spectra with those of known azaphilones and chemical correlations. In the in vitro assays, monapurones A-C (1-3) showed selective cytotoxicity against human cancer cell line A549 with IC50 values of 3.8, 2.8 and 2.4mM respectively, while exhibiting no significant toxicity to normal MRC-5 and WI-38 cells at the same concentration. Full article
Open AccessReview Biomimetic Silica Microspheres in Biosensing
Molecules 2010, 15(3), 1932-1957; https://doi.org/10.3390/molecules15031932
Received: 3 February 2010 / Revised: 16 March 2010 / Accepted: 17 March 2010 / Published: 17 March 2010
Cited by 17 | PDF Full-text (988 KB)
Abstract
Lipid vesicles spontaneously fuse and assemble into a lipid bilayer on planar or spherical silica surfaces and other substrates. The supported lipid bilayers (SLBs) maintain characteristics of biological membranes, and are thus considered to be biomembrane mimetic systems that are stable because of
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Lipid vesicles spontaneously fuse and assemble into a lipid bilayer on planar or spherical silica surfaces and other substrates. The supported lipid bilayers (SLBs) maintain characteristics of biological membranes, and are thus considered to be biomembrane mimetic systems that are stable because of the underlying substrate. Examples of their shared characteristics with biomembranes include lateral fluidity, barrier formation to ions and molecules, and their ability to incorporate membrane proteins into them. Biomimetic silica microspheres consisting of SLBs on solid or porous silica microspheres have been utilized for different biosensing applications. The advantages of such biomimetic microspheres for biosensing include their increased surface area to volume ratio which improves the detection limits of analytes, and their amenability for miniaturization, multiplexing and high throughput screening. This review presents examples and formats of using such biomimetic solid or porous silica microspheres in biosensing. Full article
(This article belongs to the Special Issue Phospholipids)
Open AccessArticle Enhanced Reactivity of [Hydroxy(tosyloxy)iodo]benzene in Fluoroalcohol Media. Efficient Direct Synthesis of Thienyl(aryl)iodonium Salts
Molecules 2010, 15(3), 1918-1931; https://doi.org/10.3390/molecules15031918
Received: 3 February 2010 / Revised: 15 March 2010 / Accepted: 16 March 2010 / Published: 17 March 2010
Cited by 28 | PDF Full-text (121 KB)
Abstract
In this manuscript, we report clear evidence for the generation of aromatic cation radicals produced by using [hydroxy(tosyloxy)iodo]benzene (HTIB) in fluoroalcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The single-electron-transfer (SET) oxidation ability of HTIB to give cation radicals was first established
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In this manuscript, we report clear evidence for the generation of aromatic cation radicals produced by using [hydroxy(tosyloxy)iodo]benzene (HTIB) in fluoroalcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The single-electron-transfer (SET) oxidation ability of HTIB to give cation radicals was first established by ESR and UV measurements. The reaction was broadly applied to various thiophenes, and unique thienyliodonium salts were directly synthesized by this method in excellent yields without the production of any harmful byproducts. Full article
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
Open AccessArticle Design, Synthesis and Anti-HIV Integrase Evaluation of N-(5-Chloro-8-Hydroxy-2-Styrylquinolin-7-yl)Benzenesulfonamide Derivatives
Molecules 2010, 15(3), 1903-1917; https://doi.org/10.3390/molecules15031903
Received: 21 October 2009 / Revised: 8 December 2009 / Accepted: 14 December 2009 / Published: 16 March 2010
Cited by 10 | PDF Full-text (221 KB)
Abstract
Styrylquinoline derivatives are demonstrated to be HIV-1 integrase inhibitors. On the basis of our previous CoMFA analysis of a series of styrylquinoline derivatives, N-[(2-substituted-styryl)-5-chloro-8-hydroxyquinolin-7-yl]-benzenesulfonamide derivatives were designed and synthesized,and their possible HIV IN inhibitory activity was evaluated. Full article
Open AccessArticle Liquid-Phase Synthesis of Cyanuric Acid from Urea
Molecules 2010, 15(3), 1898-1902; https://doi.org/10.3390/molecules15031898
Received: 30 January 2010 / Revised: 24 February 2010 / Accepted: 8 March 2010 / Published: 16 March 2010
Cited by 6 | PDF Full-text (105 KB)
Abstract
The focus of this paper was to identify a cheaper solvent from among diesel fuel, kerosene, sulfolane or a mixture of sulfolane and cyclohexanol for the preparation of cyanuric acid heterocyclization of urea. To obtain a higher yield, the effects of catalyst (sodium,
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The focus of this paper was to identify a cheaper solvent from among diesel fuel, kerosene, sulfolane or a mixture of sulfolane and cyclohexanol for the preparation of cyanuric acid heterocyclization of urea. To obtain a higher yield, the effects of catalyst (sodium, ammonium, calcium and zinc salts) and temperature (160 °C to 220 °C) on the trimerization of urea were also carefully studied. We established the optimal reaction conditions and further validated them in our scale-up experiments. Full article
Open AccessCommunication A New Triterpenoid Saponin from Pulsatilla cernua
Molecules 2010, 15(3), 1891-1897; https://doi.org/10.3390/molecules15031891
Received: 1 February 2010 / Revised: 24 February 2010 / Accepted: 9 March 2010 / Published: 16 March 2010
Cited by 8 | PDF Full-text (192 KB)
Abstract
A new triterpenoid saponin was isolated from Pulsatilla cernua, along with eight known triterpenoids and triterpenoid glycosides. The new compound was identified as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl-bayogenin-28-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (1) on the
[...] Read more.
A new triterpenoid saponin was isolated from Pulsatilla cernua, along with eight known triterpenoids and triterpenoid glycosides. The new compound was identified as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl-bayogenin-28-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (1) on the basis of 1D, 2D-NMR techniques, including COSY, HMBC, and HMQC correlations, MS analysis, as well as chemical methods. Full article
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Open AccessArticle Synthesis of Certain Pyrimidine Derivatives as Antimicrobial Agents and Anti-Inflammatory Agents
Molecules 2010, 15(3), 1882-1890; https://doi.org/10.3390/molecules15031882
Received: 11 January 2010 / Revised: 11 March 2010 / Accepted: 12 March 2010 / Published: 15 March 2010
Cited by 37 | PDF Full-text (205 KB)
Abstract
A variety of novel bicyclic and tricyclic pyrimidine derivatives was obtained via reaction of 6-amino-2-thioxo-1H-pyrimidine-4-one (1) with a different reagents. The antimicrobial and anti-inflammatory activities of some of the synthesized compounds were tested. Full article
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