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Molecules, Volume 9, Issue 11 (November 2004), Pages 902-987

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Research

Open AccessArticle Koenigs-Knorr Synthesis of Cycloalkyl Glycosides
Molecules 2004, 9(11), 902-912; doi:10.3390/91100902
Received: 14 September 2004 / Accepted: 4 October 2004 / Published: 30 November 2004
Cited by 10 | PDF Full-text (241 KB) | HTML Full-text | XML Full-text
Abstract
Cadmium carbonate was found to be a useful promoter in the Koenigs-Knorrsynthesis of 2-(4-methoxybenzyl)cyclohexyl-β-D-glycopyranosides. Using this promotermodel glucoside and galactoside derivatives of cyclic (i.e., secondary) alcohols weresynthesized in 50–60 % overall yields. Diastereoisomeric mixtures of products wereobtained in these syntheses, which started [...] Read more.
Cadmium carbonate was found to be a useful promoter in the Koenigs-Knorrsynthesis of 2-(4-methoxybenzyl)cyclohexyl-β-D-glycopyranosides. Using this promotermodel glucoside and galactoside derivatives of cyclic (i.e., secondary) alcohols weresynthesized in 50–60 % overall yields. Diastereoisomeric mixtures of products wereobtained in these syntheses, which started from racemic isomers of 2-(4-methoxy-benzyl)cyclohexanol. The prepared compounds have been purified and characterized bytheir 1H- and 13C-NMR spectra, as well as by their IR and MS spectra, in order to usethem as reference compounds in planned subsequent research. Full article
Open AccessArticle Synthesis and Biological Activities of Novel Triazole Compounds Containing 1,3-Dioxolane Rings
Molecules 2004, 9(11), 913-921; doi:10.3390/91100913
Received: 29 March 2004 / Accepted: 4 August 2004 / Published: 30 November 2004
Cited by 7 | PDF Full-text (216 KB) | HTML Full-text | XML Full-text
Abstract
Thirteen new triazoles containing 1,3-dioxolane rings were synthesized and their identities confirmed by means of IR, NMR, MS, elemental analysis and X-ray crystallography. The results of preliminary biological tests show that all of these compounds possess some fungicidal and plant growth regulant [...] Read more.
Thirteen new triazoles containing 1,3-dioxolane rings were synthesized and their identities confirmed by means of IR, NMR, MS, elemental analysis and X-ray crystallography. The results of preliminary biological tests show that all of these compounds possess some fungicidal and plant growth regulant activities. Full article
Open AccessArticle Quantum Chemical and Experimental Studies on the Mechanism of Alkylation of β-Dicarbonyl Compounds. The Synthesis of Five and Six Membered Heterocyclic Spiro Derivatives
Molecules 2004, 9(11), 922-938; doi:10.3390/91100922
Received: 5 March 2004 / Accepted: 24 June 2004 / Published: 30 November 2004
Cited by 2 | PDF Full-text (247 KB) | HTML Full-text | XML Full-text
Abstract
The alkylation of β-dicarbonyl compounds in a K2CO3/DMSO system wasfound to afford O- and C-alkylated derivatives, depending on the type of the β-dicarbonylcompound involved. The alkyl derivatives obtained were used in the synthesis of some newspiro barbituric acid [...] Read more.
The alkylation of β-dicarbonyl compounds in a K2CO3/DMSO system wasfound to afford O- and C-alkylated derivatives, depending on the type of the β-dicarbonylcompound involved. The alkyl derivatives obtained were used in the synthesis of some newspiro barbituric acid derivatives. Quantum chemical calculations were carried out toelucidate the reaction mechanisms for some typical synthesis. Full article
Open AccessArticle Asymmetric Synthesis and Antimicrobial Activity of Some New Mono and Bicyclic β-Lactams
Molecules 2004, 9(11), 939-948; doi:10.3390/91100939
Received: 24 September 2004 / Accepted: 31 August 2004 / Published: 30 November 2004
Cited by 19 | PDF Full-text (214 KB) | HTML Full-text | XML Full-text
Abstract
Reaction of the amino acid D-phenylalanine ethyl ester (4) with cinnamaldehyde gave chiral Schiff base 5, which underwent an asymmetric Staudinger [2+2] cycloaddition reaction with phthalimidoacetyl chloride to give the monocyclic β-lactam 6 as a single stereoisomer. Ozonolysis of 6 followed by [...] Read more.
Reaction of the amino acid D-phenylalanine ethyl ester (4) with cinnamaldehyde gave chiral Schiff base 5, which underwent an asymmetric Staudinger [2+2] cycloaddition reaction with phthalimidoacetyl chloride to give the monocyclic β-lactam 6 as a single stereoisomer. Ozonolysis of 6 followed by reduction with lithium aluminum tri(tert-butoxy) hydride afforded the hydroxymethyl β-lactam 8. Treatment of 8 with methansulfonyl chloride gave the mesylated monocyclic β-lactam 9, which was converted to the bicyclic β-lactam 10 upon treatment with 1,8-diazabicyclo[5,4.0] undec- 7-ene (DBU). Deprotection of the phthalimido group in β-lactams 6 and 10 by methylhydrazine and subsequent acylation of the free amino β-lactams with different acyl chlorides in the presence of pyridine afforded mono and bicyclic β-lactams 14a-d and 15a-d respectively. The compounds prepared were tested against Escherichia coli, Staphilococcus citrus, Klebsiella pneumanie and Bacillus subtillis. Some of these compounds showed potential antimicrobial activities. Full article
Open AccessArticle Synthesis and Characterization of the Complexes of Pentane-2,4-dione with Nickel(II) and Cobalt(III): [Ni(acac)2]·0.5CH3OH and [Co(acac)2NO3]·2H2O (acac = Pentane-2,4-dione)
Molecules 2004, 9(11), 949-956; doi:10.3390/91100949
Received: 10 March 2004 / Accepted: 30 August 2004 / Published: 30 November 2004
Cited by 2 | PDF Full-text (444 KB) | HTML Full-text | XML Full-text
Abstract
Two mononuclear complexes, [Ni(acac)2]·0.5CH3OH (1) and[Co(acac)2NO3]·2H2O (2) (acac = pentane-2,4-dione), have been synthesized andcharacterized by single crystal X-ray analysis. Complex 1 crystallizes in the monoclinicspace group P21/c with a = 9.295(4), b = 11.450(5), [...] Read more.
Two mononuclear complexes, [Ni(acac)2]·0.5CH3OH (1) and[Co(acac)2NO3]·2H2O (2) (acac = pentane-2,4-dione), have been synthesized andcharacterized by single crystal X-ray analysis. Complex 1 crystallizes in the monoclinicspace group P21/c with a = 9.295(4), b = 11.450(5), c = 12.974(6) å, V = 1379.1(11) å3,β = 92.854(7), and Z = 4. Complex 2 crystallizes in the triclinic space group P(-1) with a= 8.153(9), b = 9.925(11), c = 10.355(12), V = 746.3(15) å3, α = 70.530(16), β =71.154(15), γ = 80.698(16) and Z = 2. Complex 1 has a one-dimensional chain-likestructure, which is extended by weak hydrogen contacts, while complex 2 shows a three–dimensional network structure. Full article
Open AccessArticle New 1,2,3-Selenadiazole and 1,2,3-Thiadiazole Derivatives
Molecules 2004, 9(11), 957-967; doi:10.3390/91100957
Received: 13 July 2004 / Accepted: 9 September 2004 / Published: 30 November 2004
Cited by 18 | PDF Full-text (194 KB) | HTML Full-text | XML Full-text
Abstract
New 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives, 14-23, were prepared from the ketones 1-5 via the corresponding semicarbazones or hydrazones 6-12. The Hurd-Mori and Lalezari methods were used, respectively, for the preparation of these 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives. The intermediate 13 was also trapped, [...] Read more.
New 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives, 14-23, were prepared from the ketones 1-5 via the corresponding semicarbazones or hydrazones 6-12. The Hurd-Mori and Lalezari methods were used, respectively, for the preparation of these 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives. The intermediate 13 was also trapped, separated and fully characterized. These derivatives are important for photocrosslinking processes and due to their potential biological activity. Full article
Open AccessArticle Preparation of Poly(oxybutyleneoxymaleoyl) Catalyzed by a Proton Exchanged Montmorillonite Clay
Molecules 2004, 9(11), 968-977; doi:10.3390/91100968
Received: 12 July 2004 / Accepted: 6 September 2004 / Published: 30 November 2004
Cited by 3 | PDF Full-text (231 KB) | HTML Full-text | XML Full-text
Abstract
The polycondensation of tetrahydrofuran with maleic anhydride catalyzed byMaghnite-H+ (Mag-H) was investigated. Maghnite is a montmorillonite sheet silicateclay that is exchanged with protons to produce Maghnite-H [1]. It was found that thepolymerization in bulk is initiated by Mag-H in the presence [...] Read more.
The polycondensation of tetrahydrofuran with maleic anhydride catalyzed byMaghnite-H+ (Mag-H) was investigated. Maghnite is a montmorillonite sheet silicateclay that is exchanged with protons to produce Maghnite-H [1]. It was found that thepolymerization in bulk is initiated by Mag-H in the presence of acetic anhydride at 40°C.The effects of the amounts of Mag-H and acetic anhydride were studied. Thepolymerization yield increased as the proportions of catalyst and acetic anhydride wereincreased. Full article
Open AccessArticle Comparative Studies of the Effects of Two Novel Sugar Drug Candidates on the CYP 1A2 and CYP 2E1 Enzymes in Different Sexed Rats Using a “Cocktail” Approach
Molecules 2004, 9(11), 978-987; doi:10.3390/91100978
Received: 7 July 2004 / Accepted: 1 August 2004 / Published: 30 November 2004
Cited by 1 | PDF Full-text (255 KB) | HTML Full-text | XML Full-text
Abstract
The sex-based differences between the effects of two novel sugar-based drug candidates, a sulfated polymannuroguluronate (SPMG-911) and an acidic oligosaccharide sugar chain compound (AOSC-971), on the enzymes CYP 1A2 and CYP 2E1 were investigated. The results showed that neither SPMG-911 nor AOSC-971 [...] Read more.
The sex-based differences between the effects of two novel sugar-based drug candidates, a sulfated polymannuroguluronate (SPMG-911) and an acidic oligosaccharide sugar chain compound (AOSC-971), on the enzymes CYP 1A2 and CYP 2E1 were investigated. The results showed that neither SPMG-911 nor AOSC-971 have any effect on CYP1A2, while AOSC-971 induced the CYP 2E1 in male rats. The results are useful for their safety evaluation, as well as for the prediction of inter-drug interactions associated with the two drugs. Full article

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