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Molecules, Volume 11, Issue 9 (September 2006), Pages 661-730

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Research

Open AccessCommunication A Novel Triterpene from Centella asiatica
Molecules 2006, 11(9), 661-665; doi:10.3390/11090661
Received: 28 July 2006 / Revised: 11 August 2006 / Accepted: 30 August 2006 / Published: 4 September 2006
Cited by 15 | PDF Full-text (60 KB) | HTML Full-text | XML Full-text
Abstract
A novel triterpene, 2α,3β,20,23-tetrahydroxyurs-28-oic acid (1), was isolated from the aerial part of Centella asiatica. Its structure was elucidated by spectroscopic methods, including 2D-NMR spectra. It displayed no activity against Hela and A549 cell lines at concentrations of 10 and 30 μg/mL, respectively.
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A novel triterpene, 2α,3β,20,23-tetrahydroxyurs-28-oic acid (1), was isolated from the aerial part of Centella asiatica. Its structure was elucidated by spectroscopic methods, including 2D-NMR spectra. It displayed no activity against Hela and A549 cell lines at concentrations of 10 and 30 μg/mL, respectively. Full article
Open AccessArticle Synthesis and Antiviral Bioactivities of α-Aminophosphonates Containing Alkoxyethyl Moieties
Molecules 2006, 11(9), 666-676; doi:10.3390/11090666
Received: 9 August 2006 / Revised: 5 September 2006 / Accepted: 5 September 2006 / Published: 6 September 2006
Cited by 45 | PDF Full-text (178 KB) | HTML Full-text | XML Full-text
Abstract
A simple, efficient, and general method has been developed for the synthesis ofvarious α-aminophosphonate derivatives 4a-4l by treatment of substituted benzaldehydes andaniline with bis(2-methoxyethyl)- or bis(2-ethoxyethyl) phosphite under microwaveirradiation without solvents and catalysts. The products were characterized by elementalanalysis, IR, 1H-NMR, 13
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A simple, efficient, and general method has been developed for the synthesis ofvarious α-aminophosphonate derivatives 4a-4l by treatment of substituted benzaldehydes andaniline with bis(2-methoxyethyl)- or bis(2-ethoxyethyl) phosphite under microwaveirradiation without solvents and catalysts. The products were characterized by elementalanalysis, IR, 1H-NMR, 13C- and 31P-NMR spectra. The X-ray crystallographic data of therepresentative compound 4l was determined. The new α-aminophosphonate derivatives werefound to possess moderate to good antiviral activity. Full article
Open AccessArticle Cerebrosides from the Roots of Serratula chinensis
Molecules 2006, 11(9), 677-683; doi:10.3390/11090677
Received: 12 August 2006 / Revised: 31 August 2006 / Accepted: 31 August 2006 / Published: 7 September 2006
Cited by 10 | PDF Full-text (73 KB) | HTML Full-text | XML Full-text
Abstract
A new cerebroside, 1-O-β-D-glucopyranosyl-(2S,3R,8E)-2-[(2’R)-2-hydroxy- palmitoylamino]-8-octadecene-1,3-diol, along with aralia cerebroside and 1-O-β-D- glucopyranosyl-(2S,3S,4R,8E)-2-[(2’R)-2-hydroxybehenoylamino]-8-octadecene-1,3,4-triol were isolated from the roots of Serratula chinensis S. Moore. The structure of the new cerebroside was established by spectroscopic and chemical means. Occurrence of cerebrosides in Serratula is reported here
[...] Read more.
A new cerebroside, 1-O-β-D-glucopyranosyl-(2S,3R,8E)-2-[(2’R)-2-hydroxy- palmitoylamino]-8-octadecene-1,3-diol, along with aralia cerebroside and 1-O-β-D- glucopyranosyl-(2S,3S,4R,8E)-2-[(2’R)-2-hydroxybehenoylamino]-8-octadecene-1,3,4-triol were isolated from the roots of Serratula chinensis S. Moore. The structure of the new cerebroside was established by spectroscopic and chemical means. Occurrence of cerebrosides in Serratula is reported here for the first time. Full article
Open AccessArticle Synthesis and Characterisation of Eight Isomeric Bis(2-pyridyloxy)naphthalenes
Molecules 2006, 11(9), 684-692; doi:10.3390/11090684
Received: 31 July 2006 / Revised: 28 August 2006 / Accepted: 29 August 2006 / Published: 13 September 2006
Cited by 3 | PDF Full-text (321 KB) | HTML Full-text | XML Full-text
Abstract Eight isomeric bis(2-pyridyloxy)naphthalenes have been prepared from reactions of 2-bromopyridine with the appropriate dihydroxynaphthalene and the products fully characterised by 1- and 2-D NMR spectroscopy. Full article
Open AccessCommunication Cytotoxicity of Two Triterpenoids from Nigella glandulifera
Molecules 2006, 11(9), 693-699; doi:10.3390/11090693
Received: 25 July 2006 / Revised: 28 August 2006 / Accepted: 30 August 2006 / Published: 13 September 2006
Cited by 26 | PDF Full-text (174 KB) | HTML Full-text | XML Full-text
Abstract
During an investigation of antitumor substances from Nigella glandulifera Freyn et Sint. (Ranunculaceae) the cytotoxicity of two oleanane triterpene saponins isolated from the seeds of this species, kalopanaxsaponins A and I, was evaluated against HepG2, drug resistant HepG2 (R-HepG2) (two hepatocyte cell lines)
[...] Read more.
During an investigation of antitumor substances from Nigella glandulifera Freyn et Sint. (Ranunculaceae) the cytotoxicity of two oleanane triterpene saponins isolated from the seeds of this species, kalopanaxsaponins A and I, was evaluated against HepG2, drug resistant HepG2 (R-HepG2) (two hepatocyte cell lines) and primary cultured normal mouse hepatocytes. Evident cytotoxic activities were observed. Morphological observations and cell cycle analysis suggest that these compounds inhibit the proliferation of hepatoma by inducing apoptosis and consequently kalopanaxsaponins A and I may be potential therapeutic agents for the treatment of parental and drug resistant hepatoma. Full article
Open AccessArticle An Efficient Synthesis of a Spirocyclic Oxindole Analogue
Molecules 2006, 11(9), 700-706; doi:10.3390/11090700
Received: 13 August 2006 / Revised: 6 September 2006 / Accepted: 14 September 2006 / Published: 14 September 2006
Cited by 12 | PDF Full-text (67 KB) | HTML Full-text | XML Full-text
Abstract
An efficient, scaleable synthesis approach towards the spirocyclic oxindole analogue 1’-(tert-butoxycarbonyl)-2-oxospiro[indoline-3,4’-piperidine]-5-carboxylic acid (1) is described. The key steps are dianion alkylation and cyclization of ethyl 2- oxindoline-5-carboxylate (4) and demethylation of the resulting spirocyclic oxindole ethyl 1’-methyl-2-oxospiro[indoline-3,4’-piperidine]-5-carboxylate (5). The target compound was obtained
[...] Read more.
An efficient, scaleable synthesis approach towards the spirocyclic oxindole analogue 1’-(tert-butoxycarbonyl)-2-oxospiro[indoline-3,4’-piperidine]-5-carboxylic acid (1) is described. The key steps are dianion alkylation and cyclization of ethyl 2- oxindoline-5-carboxylate (4) and demethylation of the resulting spirocyclic oxindole ethyl 1’-methyl-2-oxospiro[indoline-3,4’-piperidine]-5-carboxylate (5). The target compound was obtained in an overall yield of 35 % over eight steps without resorting to chromatographic purification. Full article
Open AccessArticle Asymmetric Synthesis of (7aS)-7a-Methyl-4,5,7,7a-tetrahydro-1H-indene-2,6-dione and Useful Derivatives Thereof
Molecules 2006, 11(9), 707-713; doi:10.3390/11090707
Received: 7 September 2006 / Revised: 14 September 2006 / Accepted: 14 September 2006 / Published: 18 September 2006
PDF Full-text (52 KB) | HTML Full-text | XML Full-text
Abstract The enantioselective synthesis of the title compound, using Meyers' bicyclic lactam methodology, is described. This compound and a few of its derivatives are useful intermediates in natural product synthesis. Full article
Open AccessArticle Glycerolipids from a Sarcotragus Species Sponge
Molecules 2006, 11(9), 714-719; doi:10.3390/11090714
Received: 9 November 2005 / Revised: 27 September 2006 / Accepted: 28 September 2006 / Published: 28 September 2006
Cited by 13 | PDF Full-text (57 KB) | HTML Full-text | XML Full-text
Abstract One known and two new glycerolipids have been isolated from a Sarcotragus sp. marine sponge. The gross structures were established based on NMR and MS analysis. Full article
Open AccessCommunication Tungstate Sulfuric Acid (TSA)/ KMnO4 as a Novel Heterogeneous System for Rapid Deoximation
Molecules 2006, 11(9), 720-725; doi:10.3390/11090720
Received: 5 September 2005 / Revised: 7 June 2006 / Accepted: 30 June 2006 / Published: 28 September 2006
Cited by 21 | PDF Full-text (49 KB) | HTML Full-text | XML Full-text
Abstract
Neat chlorosulfonic acid reacts with anhydrous sodium tungstate to givetungstate sulfuric acid (TSA), a new dibasic inorganic solid acid in which two sulfuricacid molecules connect to a tungstate moiety via a covalent bond. A variety of oximeswere oxidized to their parent carbonyl compounds
[...] Read more.
Neat chlorosulfonic acid reacts with anhydrous sodium tungstate to givetungstate sulfuric acid (TSA), a new dibasic inorganic solid acid in which two sulfuricacid molecules connect to a tungstate moiety via a covalent bond. A variety of oximeswere oxidized to their parent carbonyl compounds under mild conditions with excellentyields in short times by a heterogeneous wet TSA/KMnO4 in dichloromethane system. Full article
Open AccessCommunication Synthesis of New N-Quaternary-3-benzamidoquinuclidinium Salts
Molecules 2006, 11(9), 726-730; doi:10.3390/11090726
Received: 28 July 2006 / Revised: 30 August 2006 / Accepted: 21 September 2006 / Published: 28 September 2006
Cited by 1 | PDF Full-text (74 KB) | HTML Full-text | XML Full-text
Abstract The synthesis of racemic and enantiomerically pure N-p-methylbenzyl-3- and N-p-chlorobenzylbenzamidoquinuclidinium bromides (6-8 and 9-11, respectively) is described. These compounds were prepared from racemic or enantiomerically pure 3-benzamidoquinuclidines 3-5 using the appropriate quaternization reagents: p-methyl- benzyl bromide (1) and p-chlorobenzyl bromide (2). Full article

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