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

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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; https://doi.org/10.3390/10081015 - 31 Aug 2005
Cited by 9 | Viewed by 7385
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 to [...] 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
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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; https://doi.org/10.3390/10081010 - 31 Aug 2005
Viewed by 5794
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
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Open AccessArticle
Microbial Hydroxylation of Sclareol by Rhizopus Stolonifer
Molecules 2005, 10(8), 1005-1009; https://doi.org/10.3390/10081005 - 31 Aug 2005
Cited by 9 | Viewed by 5868
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
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Open AccessArticle
The Syntheses of Some Novel (Naphthalen-1-yl-selenyl)acetic Acid Derivatives
Molecules 2005, 10(8), 1000-1004; https://doi.org/10.3390/10081000 - 31 Aug 2005
Cited by 14 | Viewed by 4723
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
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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; https://doi.org/10.3390/10080990 - 31 Aug 2005
Cited by 8 | Viewed by 4807
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
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Open AccessArticle
Synthesis and Characterization of Nitro-p-xylenes
Molecules 2005, 10(8), 978-989; https://doi.org/10.3390/10080978 - 31 Aug 2005
Cited by 3 | Viewed by 7941
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. Nitro-p-xylene [...] 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
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Open AccessArticle
Terpenoids from Cleome droserifolia (Forssk.) Del
Molecules 2005, 10(8), 971-977; https://doi.org/10.3390/10080971 - 31 Aug 2005
Cited by 29 | Viewed by 6546
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 identified [...] 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
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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; https://doi.org/10.3390/10080961 - 31 Aug 2005
Cited by 12 | Viewed by 5811
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, 1 [...] 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
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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; https://doi.org/10.3390/10080937 - 31 Aug 2005
Cited by 38 | Viewed by 8693
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 on [...] 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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Open AccessArticle
Simple and Efficient Synthesis of 2,7-Difunctionalized-1,8-Naphthyridines
Molecules 2005, 10(8), 929-936; https://doi.org/10.3390/10080929 - 31 Aug 2005
Cited by 33 | Viewed by 6843
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 (14) [...] 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
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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; https://doi.org/10.3390/10080922 - 31 Aug 2005
Cited by 7 | Viewed by 8460
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 [...] Read more.
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
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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; https://doi.org/10.3390/10080912 - 31 Aug 2005
Cited by 24 | Viewed by 8284
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 Pd(II) [...] 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
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Open AccessArticle
Synthesis of Cyclophellitol Utilizing a Palladium Chloride Mediated-Ferrier-II Rearrangement
Molecules 2005, 10(8), 901-911; https://doi.org/10.3390/10080901 - 31 Aug 2005
Cited by 4 | Viewed by 5058
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
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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; https://doi.org/10.3390/10080893 - 31 Aug 2005
Cited by 17 | Viewed by 5133
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 (3a) [...] 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
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Open AccessArticle
Bi(OTf)3 and SiO2-Bi(OTf)3 as Effective Catalysts for the Ferrier Rearrangement#
Molecules 2005, 10(8), 884-892; https://doi.org/10.3390/10080884 - 31 Aug 2005
Cited by 40 | Viewed by 5784
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
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Open AccessArticle
Towards a Synthesis of Vigabatrin Using Glycal Chemistry
Molecules 2005, 10(8), 871-883; https://doi.org/10.3390/10080871 - 31 Aug 2005
Cited by 2 | Viewed by 6580
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 explored. [...] 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
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Open AccessArticle
Epoxidation and Bis-hydroxylation of C-Phenyl-∆2,3-glycopyranosides
Molecules 2005, 10(8), 859-870; https://doi.org/10.3390/10080859 - 31 Aug 2005
Cited by 11 | Viewed by 5916
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 89:11 [...] 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
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Open AccessArticle
Triisobutylaluminium (TIBAL) Promoted Rearrangement of C-glycosides
Molecules 2005, 10(8), 843-858; https://doi.org/10.3390/10080843 - 31 Aug 2005
Cited by 6 | Viewed by 4575
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
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Open AccessArticle
Pyrimidine Acyclo-C-Nucleosides by Ring Transformations of 2-Formyl-L-arabinal
Molecules 2005, 10(8), 837-842; https://doi.org/10.3390/10080837 - 31 Aug 2005
Cited by 8 | Viewed by 5625
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
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Open AccessEditorial
Unsaturated Sugars: Syntheses and Applications. A Special Issue in Honour of Professor Kalpattu Kuppuswamy Balsubramanian
Molecules 2005, 10(8), 833-836; https://doi.org/10.3390/10080833 - 31 Aug 2005
Cited by 1 | Viewed by 2872
Abstract
Kalpattu Kuppuswamy Balsubramanian (popularly and affectionately addressed as KKB) was born on September 5th 1939, at Mylapore, Madras (now Chennai), Tamil Nadu, India, in a family gifted with tradition in the noble profession of teaching.[...] Full article
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