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Molecules, Volume 12, Issue 2 (February 2007), Pages 130-282

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Research

Open AccessArticle Radical-scavenging Activity of Natural Methoxyphenols vs. Synthetic Ones using the Induction Period Method
Molecules 2007, 12(2), 130-138; doi:10.3390/12020130
Received: 22 January 2007 / Revised: 31 January 2007 / Accepted: 1 February 2007 / Published: 3 February 2007
Cited by 9 | PDF Full-text (110 KB) | HTML Full-text | XML Full-text
Abstract
The radical-scavenging activities of the synthetic antioxidants 2-allyl-4-X-phenol (X=NO2, Cl, Br, OCH3, COCH3, CH3, t-(CH3)3, C6H5) and 2,4-dimethoxyphenol, and the natural antioxidants eugenol and isoeugenol, [...] Read more.
The radical-scavenging activities of the synthetic antioxidants 2-allyl-4-X-phenol (X=NO2, Cl, Br, OCH3, COCH3, CH3, t-(CH3)3, C6H5) and 2,4-dimethoxyphenol, and the natural antioxidants eugenol and isoeugenol, were investigated using differential scanning calorimetry (DSC) by measuring their anti-1,1-diphenyl-2-picrylhydrazyl (DPPH) radical activity and the induction period for polymerization of methyl methacrylate (MMA) initiated by thermal decomposition of 2,2'-azobisisobutyronitrile (AIBN) and benzoyl peroxide (BPO). 2-Allyl-4-methoxyphenol and 2,4-dimethoxy-phenol scavenged not only oxygen-centered radicals (PhCOO.) derived from BPO, but also carbon-centered radicals (R.) derived from the AIBN and DPPH radical much more efficiently, in comparison with eugenol and isoeugenol. 2-Allyl-4-methoxyphenol may be useful for its lower prooxidative activity. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle Antibacterial Activity of Long-Chain Fatty Alcohols against Staphylococcus aureus
Molecules 2007, 12(2), 139-148; doi:10.3390/12020139
Received: 13 January 2007 / Revised: 31 January 2007 / Accepted: 2 February 2007 / Published: 5 February 2007
Cited by 27 | PDF Full-text (99 KB) | HTML Full-text | XML Full-text
Abstract
The antibacterial activity against Staphylococcus aureus of long-chain fatty alcohols was investigated, with a focus on normal alcohols. The antibacterial activity varied with the length of the aliphatic carbon chain and not with the water/octanol partition coefficient. 1-Nonanol, 1-decanol and 1-undecanol had [...] Read more.
The antibacterial activity against Staphylococcus aureus of long-chain fatty alcohols was investigated, with a focus on normal alcohols. The antibacterial activity varied with the length of the aliphatic carbon chain and not with the water/octanol partition coefficient. 1-Nonanol, 1-decanol and 1-undecanol had bactericidal activity and membrane-damaging activity. 1-Dodecanol and 1-tridecanol had the highest antibacterial activity among the long-chain fatty alcohols tested, but had no membrane-damaging activity. Consequently, it appears that not only the antibacterial activity but also the mode of action of long-chain fatty alcohols might be determined by the length of the aliphatic carbon chain. Full article
Open AccessCommunication Comparative Chemical Analysis of the Essential Oil Constituents in the Bark, Heartwood and Fruits of Cryptocarya massoy (Oken) Kosterm. (Lauraceae) from Papua New Guinea
Molecules 2007, 12(2), 149-154; doi:10.3390/12020149
Received: 8 November 2006 / Revised: 20 December 2006 / Accepted: 3 February 2007 / Published: 5 February 2007
Cited by 22 | PDF Full-text (42 KB) | HTML Full-text | XML Full-text
Abstract
Exhaustive hydro-distillation of the bark, heartwood and fruits of Cryptocarya massoy (Lauraceae) afforded pale yellow-coloured oils in 0.7, 1.2 and 1.0 % yields, respectively. Detailed chemical evaluation of these distillates using GC/MS revealed the major components in the bark and the heartwood [...] Read more.
Exhaustive hydro-distillation of the bark, heartwood and fruits of Cryptocarya massoy (Lauraceae) afforded pale yellow-coloured oils in 0.7, 1.2 and 1.0 % yields, respectively. Detailed chemical evaluation of these distillates using GC/MS revealed the major components in the bark and the heartwood oils to be the C-10 (5,6-dihydro-6-pentyl-2H-pyran-2-one) and C-12 (5,6-dihydro-6-heptyl-2H-pyran-2-one) massoia lactones, while the major fruit oil constituent was benzyl benzoate (68.3 %). The heartwood also contained trace amounts of the C-14 (5,6-dihydro-6-nonyl-2H-pyran-2-one) massoia lactone (1.4 %) and the saturated C-10 derivative d-decalactone (2.5 %). Full article
Open AccessArticle Isatinones A and B, New Antifungal Oxindole Alkaloids from Isatis costata
Molecules 2007, 12(2), 155-162; doi:10.3390/12020155
Received: 6 January 2007 / Revised: 21 January 2007 / Accepted: 22 January 2007 / Published: 6 February 2007
Cited by 22 | PDF Full-text (90 KB) | HTML Full-text | XML Full-text
Abstract
Two new oxindole alkaloids isatinone A (1) and B (2) have been isolated from Isatis costata, along with the known trisindoline. Their structures have been assigned on the basis of spectroscopic techniques and chemical studies. Both new compounds showed significant antifungal [...] Read more.
Two new oxindole alkaloids isatinone A (1) and B (2) have been isolated from Isatis costata, along with the known trisindoline. Their structures have been assigned on the basis of spectroscopic techniques and chemical studies. Both new compounds showed significant antifungal activity. Full article
Open AccessArticle One Pot Synthesis of α-Aminophosphonates Containing Bromo and 3,4,5-Trimethoxybenzyl Groups under Solvent-free Conditions
Molecules 2007, 12(2), 163-172; doi:10.3390/12020163
Received: 26 January 2007 / Revised: 6 February 2007 / Accepted: 6 February 2007 / Published: 7 February 2007
Cited by 18 | PDF Full-text (175 KB) | HTML Full-text | XML Full-text
Abstract
New α-aminophosphonates were synthesized by the Kabachnik-Fields reactionof 3,4,5-trimethoxybenzaldehyde (TMB) with p- or m-bromoaniline and a dialkylphosphite under solvent-free conditions. TMB was prepared from gallic acid via a fourstep synthetic sequence involving etherification, esterification, hydrazidation andpotassium ferricyanide oxidation. The structures of all [...] Read more.
New α-aminophosphonates were synthesized by the Kabachnik-Fields reactionof 3,4,5-trimethoxybenzaldehyde (TMB) with p- or m-bromoaniline and a dialkylphosphite under solvent-free conditions. TMB was prepared from gallic acid via a fourstep synthetic sequence involving etherification, esterification, hydrazidation andpotassium ferricyanide oxidation. The structures of all synthesized compounds wereconfirmed by elemental analysis, IR, 1H-, 13C- and 31P-NMR spectral data. Compound 7gwas also characterized by X-ray crystallography. A half-leaf method was used todetermine the in vivo curative efficacy of the eight title products against tobacco mosaicvirus (TMV). It was found that compounds 7g and 7h possess good in vivo curativeeffects against TMV. Full article
Open AccessArticle Synthesis, NMR and Crystallographic Studies of 2-Substituted Dihydroquinazolinones Derived from (S)-Phenylethylamine
Molecules 2007, 12(2), 173-182; doi:10.3390/12020173
Received: 5 December 2006 / Revised: 2 February 2007 / Accepted: 5 February 2007 / Published: 12 February 2007
Cited by 4 | PDF Full-text (107 KB) | HTML Full-text | XML Full-text
Abstract
2,3-Dihydro-3-[(S)-1-phenethyl]quinazolinone and some new 2-substitutedderivatives bearing isopropyl, o-nitrophenyl and p-nitrophenyl groups were prepared in40-90% yield by amidation of isatoic anhydride with (S)-phenylethylamine, followed bycondensation with triethyl orthoformate, isopropylaldehyde, o-nitro- and p-nitro-benzaldehyde, respectively. The two 2-subtituted dihydroquinazolinones obtained eitherby using isopropylaldehyde, o-nitro- or [...] Read more.
2,3-Dihydro-3-[(S)-1-phenethyl]quinazolinone and some new 2-substitutedderivatives bearing isopropyl, o-nitrophenyl and p-nitrophenyl groups were prepared in40-90% yield by amidation of isatoic anhydride with (S)-phenylethylamine, followed bycondensation with triethyl orthoformate, isopropylaldehyde, o-nitro- and p-nitro-benzaldehyde, respectively. The two 2-subtituted dihydroquinazolinones obtained eitherby using isopropylaldehyde, o-nitro- or p-nitrobenzaldehyde, were separated and purifiedbefore their NMR spectra in CDCl3 solutions were recorded. The detection of the lowenergy conformation of O=C-N-phenethyl segment in solution allowed the correlation ofthe NMR data with the configuration of newly stereogenic carbon C-2; thus, onediastereomer was labeled SS while the other was RS. Configurations determined by theNMR method were corroborated by X-ray diffraction analysis. X-ray structures of eachdiastereomeric series showed characteristic conformational types: a propeller-like for theSS and a hairpin for the RS series. Interatomic distances of the hairpin conformationsuggest the existence of intramolecular face-to-face interactions between two aromaticrings. Full article
Open AccessArticle Synthesis of 3,4,7,8-Tetrahydronaphthalene-1,5(2H,6H)-dione
Molecules 2007, 12(2), 183-187; doi:10.3390/12020183
Received: 8 January 2007 / Revised: 9 February 2007 / Accepted: 11 February 2007 / Published: 13 February 2007
PDF Full-text (47 KB) | HTML Full-text | XML Full-text
Abstract A short and high yielding route for thepreparation of the title compound, starting from commercially available1,5-dihydroxynaphthalene, is described. The key step in the sequence is the airoxidation of a bis(trimethylsilyloxy)diene precursor. Full article
Open AccessArticle Synthesis and Photochemistry of 1-Iodocyclohexene:Influence of Ultrasound on Ionic vs. Radical Behaviour
Molecules 2007, 12(2), 188-193; doi:10.3390/12020188
Received: 14 December 2006 / Revised: 24 January 2007 / Accepted: 25 January 2007 / Published: 16 February 2007
Cited by 8 | PDF Full-text (413 KB) | HTML Full-text | XML Full-text
Abstract
Simultaneous application of UV light and ultrasonic irradiation to a reaction mixture containing 1-iodocyclohexene is reported. The irradiation of 1-iodocyclohexene in methanol was carried out with or without addition of zinc. The effect of ultrasound or mechanical stirring on this solid-liquid system [...] Read more.
Simultaneous application of UV light and ultrasonic irradiation to a reaction mixture containing 1-iodocyclohexene is reported. The irradiation of 1-iodocyclohexene in methanol was carried out with or without addition of zinc. The effect of ultrasound or mechanical stirring on this solid-liquid system was also compared. The irradiation of 1-iodocyclohexene in methanol in the presence of zinc increases the yield of the nucleophilic trapping product, compared with the yield after irradiation in the absence of zinc. The photodegradation of 1-iodocyclohexene was slightly accelerated after addition of zinc. A rapid formation of radical product was accompanied by substantial decrease of 1-iodocyclohexene after application of ultrasound and irradiation without the zinc. The ultrasound significantly affects the photobehaviour of this reaction, predominantly its radical route. The joint application of ultrasound and zinc contributes positively to the production of radical and ionic products. The sonochemical stirring is more effective than mechanical stirring. Full article
Open AccessArticle Synthesis of 2,5-Disubstituted Octahydroquinolin-4-ones via anIntramolecular Hetero Diels-Alder Reaction
Molecules 2007, 12(2), 194-204; doi:10.3390/12020194
Received: 25 January 2007 / Revised: 13 February 2007 / Accepted: 13 February 2007 / Published: 19 February 2007
Cited by 3 | PDF Full-text (79 KB) | HTML Full-text | XML Full-text
Abstract
A route for the preparation of 2,5-disubstituted octahydroquinolin-4-ones, synthetic precursors of the decahydroquinoline-type toxins, is presented. The key steps are an asymmetric epoxidation and an intramolecular hetero Diels-Alder reaction between an activated diene and an imine. The presence of an allylic stereogenic [...] Read more.
A route for the preparation of 2,5-disubstituted octahydroquinolin-4-ones, synthetic precursors of the decahydroquinoline-type toxins, is presented. The key steps are an asymmetric epoxidation and an intramolecular hetero Diels-Alder reaction between an activated diene and an imine. The presence of an allylic stereogenic center induces some selectivity and thus only two cycloadducts are obtained in 70:30 ratio and good yield. Full article
Open AccessArticle A Novel Antioxidant Phenyl Disaccharide from Populus tremula Knotwood
Molecules 2007, 12(2), 205-217; doi:10.3390/12020205
Received: 8 January 2007 / Revised: 15 February 2007 / Accepted: 18 February 2007 / Published: 19 February 2007
Cited by 2 | PDF Full-text (157 KB) | HTML Full-text | XML Full-text
Abstract
The complete characterization of two compounds obtained from the acetoneextract of Populus tremula knotwood has been was achieved using LC-DAD-MS,MS/MS, IR and NMR. The new compounds were unequivocally identified as a mixtureof the ester isomers of the (E) and (Z) p-coumarate of [...] Read more.
The complete characterization of two compounds obtained from the acetoneextract of Populus tremula knotwood has been was achieved using LC-DAD-MS,MS/MS, IR and NMR. The new compounds were unequivocally identified as a mixtureof the ester isomers of the (E) and (Z) p-coumarate of 1-O-rutinose. The isomers showedthe capacity to inhibit lipid peroxidation induced by tert-butylhydroperoxide and to trapperoxyl radicals, as determined by a chemiluminescence method. These new phenyldisaccharides also showed a significant ORAC (oxygen radical absorbance capacity)value, i.e. 11.7 μM TE (Trolox Equivalents). Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle Novel 2-Chloro-8-arylthiomethyldipyridodiazepinone Derivatives with Activity against HIV-1 Reverse Transcriptase
Molecules 2007, 12(2), 218-230; doi:10.3390/12020218
Received: 22 December 2006 / Revised: 18 February 2007 / Accepted: 19 February 2007 / Published: 20 February 2007
Cited by 6 | PDF Full-text (127 KB) | HTML Full-text | XML Full-text
Abstract
Based on the molecular modeling analysis against Y181CHIV-1 RT, dipyridodiazepinone derivatives containing an unsubstituted lactamnitrogen and 2-chloro-8-arylthiomethyl were synthesized via an efficientroute. Some of them were evaluated for their antiviral activity against HIV-1RT subtype E and were found to exhibit virustatic activity [...] Read more.
Based on the molecular modeling analysis against Y181CHIV-1 RT, dipyridodiazepinone derivatives containing an unsubstituted lactamnitrogen and 2-chloro-8-arylthiomethyl were synthesized via an efficientroute. Some of them were evaluated for their antiviral activity against HIV-1RT subtype E and were found to exhibit virustatic activity comparable to some clinically usedtherapeutic agents. Full article
Open AccessCommunication Efficient Preparation of Aldoximes from Arylaldehydes, Ethylenediamine and Oxone® in Water
Molecules 2007, 12(2), 231-236; doi:10.3390/12020231
Received: 25 January 2007 / Revised: 14 February 2007 / Accepted: 18 February 2007 / Published: 21 February 2007
Cited by 11 | PDF Full-text (47 KB) | HTML Full-text | XML Full-text
Abstract The one-pot reaction of aromatic aldehydes, ethylenediamine and Oxone® (2KHSO5·KHSO4·K2SO4) in pure water was found to unexpectedly afford aldoximes in excellent yields. Full article
Open AccessArticle Asymmetric Synthesis of the Epimeric (3S)-3-((E)-Hex-1-enyl)-2-methylcyclohexanones
Molecules 2007, 12(2), 237-244; doi:10.3390/12020237
Received: 9 January 2007 / Revised: 20 February 2007 / Accepted: 20 February 2007 / Published: 21 February 2007
Cited by 2 | PDF Full-text (80 KB) | HTML Full-text | XML Full-text
Abstract
The asymmetric rhodium-catalysed 1,4-addition of alkenylzirconium reagents to 2-cyclohexenone can be useful in the synthesis of 3-alkenyl-2-methylcyclohexanones, provided that formaldehyde is used in trapping the intermediate zirconium enolates. In this manner a four-step sequence leading to the two epimeric 3-hexenyl-2-methylcyclohexanones in enantiomeric [...] Read more.
The asymmetric rhodium-catalysed 1,4-addition of alkenylzirconium reagents to 2-cyclohexenone can be useful in the synthesis of 3-alkenyl-2-methylcyclohexanones, provided that formaldehyde is used in trapping the intermediate zirconium enolates. In this manner a four-step sequence leading to the two epimeric 3-hexenyl-2-methylcyclohexanones in enantiomeric form was developed. Full article
Open AccessArticle Synthesis, Characterization and AntibacterialActivity of Azomethine Derivatives Derived from 2-Formylphenoxyacetic Acid
Molecules 2007, 12(2), 245-254; doi:10.3390/12020245
Received: 10 February 2007 / Revised: 20 February 2007 / Accepted: 21 February 2007 / Published: 22 February 2007
Cited by 22 | PDF Full-text (91 KB) | HTML Full-text | XML Full-text
Abstract
A series of eight new azomethine derivatives were synthesized by reacting 2-formylphenoxyacetic acid with aromatic amines. The chemical structures of these compounds were confirmed by means of 1H-NMR, 13C-NMR, MS and elemental analysis. The compounds were assayed by the disc [...] Read more.
A series of eight new azomethine derivatives were synthesized by reacting 2-formylphenoxyacetic acid with aromatic amines. The chemical structures of these compounds were confirmed by means of 1H-NMR, 13C-NMR, MS and elemental analysis. The compounds were assayed by the disc diffusion method for antibacterial against Staphylococcus aureus and Escherichia coli. Among the compounds tested, 2a, 2b, 2e, 2g and 2h exhibited good antibacterial activity, almost equal to that of Ciprofloxacin used as standard. Full article
Open AccessArticle Heteropolyacids as Green and Reusable Catalysts for the Synthesis of 3,1,5-Benzoxadiazepines
Molecules 2007, 12(2), 255-262; doi:10.3390/12020255
Received: 8 January 2007 / Revised: 10 February 2007 / Accepted: 12 February 2007 / Published: 26 February 2007
Cited by 27 | PDF Full-text (73 KB) | HTML Full-text | XML Full-text
Abstract Synthesis of 3,1,5-benzoxadiazepines from the condensation of o-phenylenediamine (o-PDA) and acyl chlorides in the presence of a catalytic amount of various heteropolyacids (HPAs) is reported. Full article
(This article belongs to the Special Issue Heterocycles)
Open AccessArticle Reactive Oxygen Species Scavenging Activity of Flavone Glycosides from Melilotus neapolitana
Molecules 2007, 12(2), 263-270; doi:10.3390/12020263
Received: 21 January 2007 / Revised: 13 February 2007 / Accepted: 27 February 2007 / Published: 28 February 2007
Cited by 14 | PDF Full-text (78 KB) | HTML Full-text | XML Full-text
Abstract
One new and six known flavone glycosides were isolated from the MeOH extract of Melilotus neapolitana Ten. The new compound, identified as 7-O-β-D-gluco-pyranosyloxy-4',5-dihydroxy-3-[O-α-L-rhamnopyranosyl-(1→6)-3-O-β-D-glucopyrano-syloxy]flavone (1) by 1D and 2D NMR techniques and mass spectra, was isolated along with kaempferol-3-O-rutinoside (2), kaempferol-3-O-glucoside (3), rutin [...] Read more.
One new and six known flavone glycosides were isolated from the MeOH extract of Melilotus neapolitana Ten. The new compound, identified as 7-O-β-D-gluco-pyranosyloxy-4',5-dihydroxy-3-[O-α-L-rhamnopyranosyl-(1→6)-3-O-β-D-glucopyrano-syloxy]flavone (1) by 1D and 2D NMR techniques and mass spectra, was isolated along with kaempferol-3-O-rutinoside (2), kaempferol-3-O-glucoside (3), rutin (4), quercetin-3-O-glucoside (5), isorhamnetin-3-O-rutinoside (6), and isorhamnetin-3-O-glucoside (7). The antioxidant and radical scavenging activities of these compounds and the whole crude methanol extract were evaluated. The organic extract can inhibit MDA marker’s synthesis by 57%. All the metabolites displayed good reducing power, with the kaempferol (2,3) and isorhamnetin derivatives (6,7) being less active than the corresponding quercetin derivatives 4,5. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle Synthesis and Biological Evaluation of Rigid Polycyclic Derivatives of the Diels-Alder Adduct Tricyclo[6.2.1.02,7]undeca-4,9-dien-3,6-dione
Molecules 2007, 12(2), 271-282; doi:10.3390/12020271
Received: 30 January 2007 / Revised: 14 February 2007 / Accepted: 16 February 2007 / Published: 27 February 2007
Cited by 20 | PDF Full-text (88 KB) | HTML Full-text | XML Full-text
Abstract
art of our research program concentrates on the discovery of new bioactivecompounds prepared either by total synthesis or molecular transformation of compoundswith bioactivity profiles. In this work we have focused our interest on chemicaltransformations of the Diels-Alder adduct tricyclo[6.2.1.02,7]undeca-4,9-dien-3,6-dione inorder [...] Read more.
art of our research program concentrates on the discovery of new bioactivecompounds prepared either by total synthesis or molecular transformation of compoundswith bioactivity profiles. In this work we have focused our interest on chemicaltransformations of the Diels-Alder adduct tricyclo[6.2.1.02,7]undeca-4,9-dien-3,6-dione inorder to obtain cage-like compounds and derivatives, followed by an evaluation of theirbiological activity. Full article

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