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Molecules, Volume 10, Issue 8 (August 2005), Pages 833-1020

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Editorial

Jump to: Research, Review

Open AccessEditorial Unsaturated Sugars: Syntheses and Applications. A Special Issue in Honour of Professor Kalpattu Kuppuswamy Balsubramanian
Molecules 2005, 10(8), 833-836; doi:10.3390/10080833
Received: 3 April 2005 / Published: 31 August 2005
PDF Full-text (43 KB) | HTML Full-text | XML Full-text

Research

Jump to: Editorial, Review

Open AccessArticle Pyrimidine Acyclo-C-Nucleosides by Ring Transformations of 2-Formyl-L-arabinal
Molecules 2005, 10(8), 837-842; doi:10.3390/10080837
Received: 29 September 2004 / Revised: 5 April 2005 / Accepted: 5 April 2005 / Published: 31 August 2005
Cited by 6 | PDF Full-text (59 KB) | HTML Full-text | XML Full-text
Abstract The protected 2-formyl-L-arabinal 2 reacted with thiourea and cyanamide in the presence of sodium hydride to afford via ring transformations the 5-[1R,2S-1,2- bis(benzyloxy)-3-hydroxypropyl]-1,2-dihydropyrimidines 3 and 4, respectively. Similarly, treatment of 2 with 3-amino-2H-1,2,4-triazole yielded 6-[1R,2S-1,2- bis(benzyloxy)-3-hydroxypropyl][1,2,4]-triazolo[1,5-a]pyrimidine (5). Full article
Open AccessArticle Triisobutylaluminium (TIBAL) Promoted Rearrangement of C-glycosides
Molecules 2005, 10(8), 843-858; doi:10.3390/10080843
Received: 8 October 2004 / Revised: 4 November 2004 / Accepted: 10 November 2004 / Published: 31 August 2005
Cited by 5 | PDF Full-text (179 KB) | HTML Full-text | XML Full-text
Abstract Triisobutylaluminium-promoted rearrangement of unsaturated glycosides containing electron-donating aglycons, such as C-aryl glycosides, provides direct access to highly functionalised cyclohexane derivatives. Full article
Open AccessArticle Epoxidation and Bis-hydroxylation of C-Phenyl-∆2,3-glycopyranosides
Molecules 2005, 10(8), 859-870; doi:10.3390/10080859
Received: 1 October 2004 / Revised: 13 October 2004 / Accepted: 15 October 2004 / Published: 31 August 2005
Cited by 8 | PDF Full-text (98 KB) | HTML Full-text | XML Full-text
Abstract
Epoxidation and cis-hydroxylation of C-phenyl-∆2,3-glycopyranosides have beencarried out with a view to developing C-aryl glycoside synthesis. Epoxidation of (2,3- and (6-O-tert-butyldimethylsilyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)benzenedideoxy-D-erythro-hex-2-enopyranosyl)benzene gave predominantly the allo-adductswhatever the configuration at the anomeric center. Epoxidation of (4,6-di-O-tert-butyl-dimethylsilyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)benzene gave the manno- andallo-adducts in a [...] Read more.
Epoxidation and cis-hydroxylation of C-phenyl-∆2,3-glycopyranosides have beencarried out with a view to developing C-aryl glycoside synthesis. Epoxidation of (2,3- and (6-O-tert-butyldimethylsilyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)benzenedideoxy-D-erythro-hex-2-enopyranosyl)benzene gave predominantly the allo-adductswhatever the configuration at the anomeric center. Epoxidation of (4,6-di-O-tert-butyl-dimethylsilyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)benzene gave the manno- andallo-adducts in a 89:11 and 40:60 ratios for the α- and β-anomers, respectively.Hydroxylation of α-C-phenyl-∆2,3-glycopyranosides using OsO4 afforded the manno-adductonly, whatever the substituents at positions 4 and 6, whereas hydroxylation of (2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)benzene and (4,6-di-O-tert-butyldimethylsilyl-2,3-dideoxy- β-D-erythro-hex-2-enopyranosyl)benzene gave the manno- and allo-adducts in25:75 and 80:20 ratios, respectively. Full article
Open AccessArticle Towards a Synthesis of Vigabatrin Using Glycal Chemistry
Molecules 2005, 10(8), 871-883; doi:10.3390/10080871
Received: 24 October 2004 / Revised: 8 December 2004 / Accepted: 7 January 2005 / Published: 31 August 2005
Cited by 2 | PDF Full-text (99 KB) | HTML Full-text | XML Full-text
Abstract
Application of the Ferrier rearrangement led to a novel carbohydrate based synthetic route to 4-aminohexenoic acid viz. (R) and (S)-vigabatrin. The potential of D- glucose or D-galactose as the chiral starting materials for the synthesis of (R) and (S)- vigabatrin has been [...] Read more.
Application of the Ferrier rearrangement led to a novel carbohydrate based synthetic route to 4-aminohexenoic acid viz. (R) and (S)-vigabatrin. The potential of D- glucose or D-galactose as the chiral starting materials for the synthesis of (R) and (S)- vigabatrin has been explored. Full article
Open AccessArticle Bi(OTf)3 and SiO2-Bi(OTf)3 as Effective Catalysts for the Ferrier Rearrangement#
Molecules 2005, 10(8), 884-892; doi:10.3390/10080884
Received: 9 November 2004 / Revised: 7 February 2005 / Accepted: 7 February 2005 / Published: 31 August 2005
Cited by 36 | PDF Full-text (137 KB) | HTML Full-text | XML Full-text
Abstract Bi(OTf)3 and SiO2-Bi(OTf)3 are found to effectively catalyze the Ferrierrearrangement of tri-O-acetyl glycals with different alcohols providing an effective routeto 2,3-unsaturated O-glycosides with good anomeric selectivity and good to excellentyields after short reaction times. Full article
Open AccessArticle The 5-Endo-trig Cyclization of D-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxycastanospermine and its 8a-epi-Analogue†
Molecules 2005, 10(8), 893-900; doi:10.3390/10080893
Received: 15 October 2004 / Revised: 4 January 2005 / Accepted: 10 January 2005 / Published: 31 August 2005
Cited by 13 | PDF Full-text (126 KB) | HTML Full-text | XML Full-text
Abstract
The intramolecular aminomercuration of γ-alkenylamines 1a, 1b and 4 was shown to afford the 5-endo-trig cyclized product exclusively in good yield. The utility of pyrrolidine derivatives thus obtained from D-glucose derived γ-alkenylamines 1a and 1b was demonstrated in the synthesis of 1-deoxycastanospermine [...] Read more.
The intramolecular aminomercuration of γ-alkenylamines 1a, 1b and 4 was shown to afford the 5-endo-trig cyclized product exclusively in good yield. The utility of pyrrolidine derivatives thus obtained from D-glucose derived γ-alkenylamines 1a and 1b was demonstrated in the synthesis of 1-deoxycastanospermine (3a) and 1-deoxy-8a-epi- castanospermine (3b). Full article
Open AccessArticle Synthesis of Cyclophellitol Utilizing a Palladium Chloride Mediated-Ferrier-II Rearrangement
Molecules 2005, 10(8), 901-911; doi:10.3390/10080901
Received: 2 January 2005 / Accepted: 5 January 2005 / Published: 31 August 2005
Cited by 3 | PDF Full-text (137 KB) | HTML Full-text | XML Full-text
Abstract Cyclophellitol and its C3-epimer have been synthesized from5-enoglucopyranoside and 5-enomannopyranoside, respectively. The carbocyclic skeletonwas constructed through a Ferrier-II reaction meditated by PdCl2. Full article
Open AccessArticle A New iso-Amyl Benzothiazolyl Sulfoxide as an Extractant for Palladium and the Crystal Structure of its Palladium (II) Complex
Molecules 2005, 10(8), 912-921; doi:10.3390/10080912
Received: 12 September 2004 / Revised: 6 February 2005 / Accepted: 15 February 2005 / Published: 31 August 2005
Cited by 16 | PDF Full-text (227 KB) | HTML Full-text | XML Full-text
Abstract
A new iso-amyl benzothiazolyl sulfoxide (ABSO) was synthesized and used inthe extraction of Pd(II) from hydrochloric acid media. Pd(II) was extracted quantitativelyfrom 0.1 M HCl with ABSO in benzene (0.5 M). Ammonia solution (2.0 M) could beused as stripping agent. ABSO and [...] Read more.
A new iso-amyl benzothiazolyl sulfoxide (ABSO) was synthesized and used inthe extraction of Pd(II) from hydrochloric acid media. Pd(II) was extracted quantitativelyfrom 0.1 M HCl with ABSO in benzene (0.5 M). Ammonia solution (2.0 M) could beused as stripping agent. ABSO and Pd(II) form a 2:1 adduct [Pd (ABSO)2Cl2] in theextraction. X-ray crystal structure determination revealed PdCl2(ABSO)2 is asquare-planar complex in which ABSO acts as a neutral unidentate ligand coordinatedwith palladium(II) via the thiazolyl N atom. Full article
Open AccessArticle Investigation of Antioxidant Vitamins (A, E, C) and Lipid Peroxidation Levels in Rats Injected N-(1,3-Benzothiazol-2-yl)-N-(4,5-dihydro-1H-imidazol-2-yl) amine
Molecules 2005, 10(8), 922-928; doi:10.3390/10080922
Received: 4 September 2004 / Revised: 16 March 2005 / Accepted: 20 March 2005 / Published: 31 August 2005
Cited by 7 | PDF Full-text (118 KB) | HTML Full-text | XML Full-text
Abstract
The present study examined the influence of synthetic N-(1,3-benzothiazol-2-yl)-N-(4,5-dihydro-1H-imidazol-2-yl) amine (2-Amdz) on levels of vitamins A, E and C and malondialdehyde (MDA) in rats. A total of 30 rats, divided into two groups, were used in the study. The control group was given only a subcutaneous injection of 250 ?L 75% ethanol, every other day. The other group of rats was administered a subcutaneous injection of 2-Amdz (25 mg kg-1, dissolved in 250 ?L of 75% ethanol). Injections were continued for 16 days. After the application of 2-Amdz for 16 days, the serum levels of vitamins A, E and C and malondialdehyde (MDA) were determined by HPLC. The serum vitamin A, E, and C levels decreased significantly compared to controls (p<0.05) whereas serum MDA levels were higher than control levels (p<0.005). As a result, it can be suggested that 2-Amdz induced a severe stress and more importantly, increased the amount of free radicals and significantly decreased the levels of serum antioxidant vitamins. Full article
Open AccessArticle Simple and Efficient Synthesis of 2,7-Difunctionalized-1,8-Naphthyridines
Molecules 2005, 10(8), 929-936; doi:10.3390/10080929
Received: 25 August 2004 / Revised: 23 November 2004 / Accepted: 6 January 2005 / Published: 31 August 2005
Cited by 25 | PDF Full-text (59 KB) | HTML Full-text | XML Full-text
Abstract
The syntheses in good yields of some new difunctionalized 1,8-naphthyridines 4, 6, 8 and 9 and a novel triethylene glycol ether-linked dinaphthyridine, 10a, along with the mononaphthyridine-linked ether alcohol 10b are described. An improved and milder method for the synthesis of 2,7-diamino-1,8-naphthyridine [...] Read more.
The syntheses in good yields of some new difunctionalized 1,8-naphthyridines 4, 6, 8 and 9 and a novel triethylene glycol ether-linked dinaphthyridine, 10a, along with the mononaphthyridine-linked ether alcohol 10b are described. An improved and milder method for the synthesis of 2,7-diamino-1,8-naphthyridine (14) is also reported. Full article
Open AccessArticle Synthesis and Non-Aqueous Medium Titrations of Some New 4-Benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives
Molecules 2005, 10(8), 961-970; doi:10.3390/10080961
Received: 26 August 2004 / Revised: 9 April 2005 / Accepted: 10 April 2005 / Published: 31 August 2005
Cited by 11 | PDF Full-text (294 KB) | HTML Full-text | XML Full-text
Abstract
The synthesis of 3-alkyl(aryl)-4-(3-ethoxy-4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones 3 from the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones 2 with 3-ethoxy-4-hydroxybenzaldehyde is described.The acetylation and methylation reactions of the compounds 3 giving compounds of type4 and 5, respectively, were investigated. The newly synthesized compounds werecharacterized using elemental analyses and IR, [...] Read more.
The synthesis of 3-alkyl(aryl)-4-(3-ethoxy-4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones 3 from the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones 2 with 3-ethoxy-4-hydroxybenzaldehyde is described.The acetylation and methylation reactions of the compounds 3 giving compounds of type4 and 5, respectively, were investigated. The newly synthesized compounds werecharacterized using elemental analyses and IR, 1H-NMR, 13C-NMR and UV spectral data.In addition, to investigate the effects of solvents and molecular structure upon acidity,compounds 3 were titrated potentiometrically with tetrabutylammonium hydroxide infour non-aqueous solvents (isopropyl alcohol, tert-butyl alcohol, acetonitrile and N,N-dimethylformamide). The half-neutralization potential values and the corresponding pKavalues were determined for all cases. Full article
Open AccessArticle Terpenoids from Cleome droserifolia (Forssk.) Del
Molecules 2005, 10(8), 971-977; doi:10.3390/10080971
Received: 23 January 2005 / Revised: 15 April 2005 / Accepted: 17 April 2005 / Published: 31 August 2005
Cited by 20 | PDF Full-text (243 KB) | HTML Full-text | XML Full-text
Abstract
A new diacetyl triterpene lactone, drosericarpone (2), was isolated from the hexane extract of the herb Cleome droserifolia, together with buchariol (1, a sesquiterpene oxide, isolated for the first time from Cleome species) and stigmasterol glucoside (3). The structures of 1-3 were [...] Read more.
A new diacetyl triterpene lactone, drosericarpone (2), was isolated from the hexane extract of the herb Cleome droserifolia, together with buchariol (1, a sesquiterpene oxide, isolated for the first time from Cleome species) and stigmasterol glucoside (3). The structures of 1-3 were identified by spectroscopic means. Full article
Open AccessArticle Synthesis and Characterization of Nitro-p-xylenes
Molecules 2005, 10(8), 978-989; doi:10.3390/10080978
Received: 25 January 2004 / Revised: 23 April 2005 / Accepted: 25 April 2005 / Published: 31 August 2005
Cited by 2 | PDF Full-text (418 KB) | HTML Full-text | XML Full-text
Abstract
In this paper we elected to nitrate p-xylene because this compound has onlyone mononitro- and trinitro- isomer. Trinitro-p-xylene was used as a starting material forthe synthesis of other compounds in subsequent work. The mononitration of p-xylene canbe easily carried out at 30°C. [...] Read more.
In this paper we elected to nitrate p-xylene because this compound has onlyone mononitro- and trinitro- isomer. Trinitro-p-xylene was used as a starting material forthe synthesis of other compounds in subsequent work. The mononitration of p-xylene canbe easily carried out at 30°C. Nitro-p-xylene is easily nitrated to dinitro-p-xylene at atemperature of 80°C. The trinitro-p-xylene can be obtained at 120°C. Single crystals of2,3-dinitro-p-xylene and 2,3,5-trinitro-p-xylene were grown using theslow cooling method and we report the X-ray structure of the former. The thermaldecomposition of the compounds was studied using differential scanning calorimetry(DSC) and thermogravimetry-derivative thermogravimetry (TG-DTG) techniques andFT-IR. The target compounds were also characterized by 1H-NMR, 13C-NMR and MS. Full article
Open AccessArticle Synthesis of 4'-(2,6,6-Trimethyl -2-Cyclohexen-1-yl) -3'-Buten-2'-Ketoxime-N-O-Alkyl Ethers
Molecules 2005, 10(8), 990-999; doi:10.3390/10080990
Received: 2 April 2005 / Revised: 23 April 2005 / Accepted: 25 April 2005 / Published: 31 August 2005
Cited by 7 | PDF Full-text (131 KB) | HTML Full-text | XML Full-text
Abstract 4'-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3'-buten-2'-ketoxime-N-O-alkyl ethershave been synthesized starting from α-ionone, separated into their E and Z isomers andcharacterized on the basis of 1H-NMR and mass spectra. Full article
Open AccessArticle The Syntheses of Some Novel (Naphthalen-1-yl-selenyl)acetic Acid Derivatives
Molecules 2005, 10(8), 1000-1004; doi:10.3390/10081000
Received: 11 February 2005 / Revised: 29 April 2005 / Accepted: 30 April 2005 / Published: 31 August 2005
Cited by 10 | PDF Full-text (204 KB) | HTML Full-text | XML Full-text
Abstract Some new (naphthalen-1-yl-selenyl)acetic acids derivatives 7a-d have been synthesized by two different methods, using naphthylselenols or naphthylselenocyanates. The structures of the products were investigated by spectroscopic methods. Full article
Open AccessArticle Microbial Hydroxylation of Sclareol by Rhizopus Stolonifer
Molecules 2005, 10(8), 1005-1009; doi:10.3390/10081005
Received: 13 May 2005 / Revised: 5 July 2005 / Accepted: 5 July 2005 / Published: 31 August 2005
Cited by 8 | PDF Full-text (55 KB) | HTML Full-text | XML Full-text
Abstract Incubation of sclareol with Rhizopus stolonifer affords in high yield a mixture of triols with 18-hydroxy-sclareol as the main component. Full article
Open AccessArticle Preparation of an Eight-Membered Sesquiterpene Lactone Resulting from Sequential Gif System GoAggIII and MCPBA Oxidation of ( )-10β,14-Dihydroxy-allo-aromadendrane
Molecules 2005, 10(8), 1010-1014; doi:10.3390/10081010
Received: 8 December 2004 / Accepted: 2 March 2005 / Published: 31 August 2005
PDF Full-text (106 KB) | HTML Full-text | XML Full-text
Abstract Studies aimed at a comparison of chemical, biomimetic (Gif system GoAggIII)and enzymatic (CHMO) transformations of natural ( )-10β,14-dihydroxy-allo-aromadendrane have led to preparation of an eight-member sesquiterpene lactone. Full article
Open AccessArticle Improved Synthesis of β-D-6-Methylpurine Riboside and Antitumor Effects of the β-D- and α-D-Anomers
Molecules 2005, 10(8), 1015-1020; doi:10.3390/10081015
Received: 10 December 2004 / Revised: 27 May 2005 / Accepted: 26 May 2005 / Published: 31 August 2005
Cited by 7 | PDF Full-text (53 KB) | HTML Full-text | XML Full-text
Abstract
6-Methylpurine-β-D-riboside (β-D-MPR) has been synthesized by coupling6-methylpurine and 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribose using conditions that producethe β-D-anomer exclusively. The in vitro antitumor effects of β-D-MPR and 6-methyl-purine-α-D-riboside (α-D-MPR) in five human tumor cell lines showed that β-D-MPR washighly active (IC50 values ranging from 6 [...] Read more.
6-Methylpurine-β-D-riboside (β-D-MPR) has been synthesized by coupling6-methylpurine and 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribose using conditions that producethe β-D-anomer exclusively. The in vitro antitumor effects of β-D-MPR and 6-methyl-purine-α-D-riboside (α-D-MPR) in five human tumor cell lines showed that β-D-MPR washighly active (IC50 values ranging from 6 to 34 nM). α-D-MPR, although less active than β-D-MPR, also exhibited significant antitumor effects (IC50 values ranging from 1.47 to 4.83"µ"M). Full article

Review

Jump to: Editorial, Research

Open AccessReview Reactions of 3-Formylchromone with Active Methylene and Methyl Compounds and Some Subsequent Reactions of the Resulting Condensation Products
Molecules 2005, 10(8), 937-960; doi:10.3390/10080937
Received: 12 March 2004 / Revised: 8 February 2005 / Accepted: 10 March 2005 / Published: 31 August 2005
Cited by 31 | PDF Full-text (295 KB) | HTML Full-text | XML Full-text
Abstract
This review presents a survey of the condensations of 3-formylchromone with various active methylene and methyl compounds, e.g. malonic or barbituric acid derivatives, five-membered heterocycles, etc. The utilisation of the condensation products for the synthesis of different heterocyclic systems, which is based [...] Read more.
This review presents a survey of the condensations of 3-formylchromone with various active methylene and methyl compounds, e.g. malonic or barbituric acid derivatives, five-membered heterocycles, etc. The utilisation of the condensation products for the synthesis of different heterocyclic systems, which is based on the ability of the γ-pyrone ring to be opened by the nucleophilic attack is also reviewed. Finally, the applications of microwave irradiation as an unconventional method of reaction activation in the synthesis of condensation products is described and the biological activity of some chromone derivatives is noted. Full article

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