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Molecules, Volume 10, Issue 11 (November 2005), Pages 1364-1428

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Research

Open AccessArticle Alumina and Silica Oxides as Catalysts for the Oxidation of Benzoins to Benzils under Solvent-free Conditions
Molecules 2005, 10(11), 1364-1368; doi:10.3390/10111364
Received: 5 February 2005 / Accepted: 5 March 2005 / Published: 30 November 2005
Cited by 9 | PDF Full-text (59 KB) | HTML Full-text | XML Full-text
Abstract
Alumina or silica gel are used as catalysts for a solvent-free oxidation of benzoins to the corresponding benzils. These catalysts are easily recovered after completion of the reactions, which are carried out either by heating in a sand bath or using microwave irradiation.
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Alumina or silica gel are used as catalysts for a solvent-free oxidation of benzoins to the corresponding benzils. These catalysts are easily recovered after completion of the reactions, which are carried out either by heating in a sand bath or using microwave irradiation. Comparison of the results obtained with both catalysts indicates that all the reactants examined were oxidized faster on alumina than on silica under these conditions. Full article
Open AccessArticle Synthesis and Bioactivity of New Phosphorylated R,R’-substituted Sulfoximines
Molecules 2005, 10(11), 1369-1376; doi:10.3390/10111369
Received: 20 January 2005 / Revised: 24 January 2005 / Accepted: 14 March 2005 / Published: 30 November 2005
Cited by 2 | PDF Full-text (64 KB) | HTML Full-text | XML Full-text
Abstract
R,R’-disubstituted sulfoximines were phosphorylated with O,O–diethylchlorophosphate and phosphorothionate to obtain new organophosphorus compounds. Afterpurification they were characterized by GC-MS and 1H-NMR. The toxicity of thesynthesized O,O-diethyl N-(R,R’-disubstituted sulfoximine) phosphoro-amidothionateswas assayed on Musca domestica. It was found that the methyl phenyl derivative was
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R,R’-disubstituted sulfoximines were phosphorylated with O,O–diethylchlorophosphate and phosphorothionate to obtain new organophosphorus compounds. Afterpurification they were characterized by GC-MS and 1H-NMR. The toxicity of thesynthesized O,O-diethyl N-(R,R’-disubstituted sulfoximine) phosphoro-amidothionateswas assayed on Musca domestica. It was found that the methyl phenyl derivative was themost toxic compound, followed by the dipropyl and dibutyl derivatives. The dihexylcompound was the less toxic of all the assayed compounds, being one hundred times lesstoxic than a paraoxon standard The anticholinesterasic activity of the correspondingphosphoramidates was assayed on homogenates of house flies’ heads, giving valuessimilar to paraoxon for the methyl phenyl derivative. Full article
Open AccessArticle Synthesis and Potent Antimicrobial Activity of Some Novel N-(Alkyl)-2-Phenyl-1H-Benzimidazole-5-Carboxamidines
Molecules 2005, 10(11), 1377-1386; doi:10.3390/10111377
Received: 7 June 2005 / Revised: 25 October 2005 / Accepted: 26 November 2005 / Published: 30 November 2005
Cited by 36 | PDF Full-text (143 KB) | HTML Full-text | XML Full-text
Abstract
A series of 22 novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5- carboxamidine derivatives were synthesized and evaluated for in vitro antibacterial activity against S. aureus and methicillin resistant S. aureus (MRSA), E. coli, E. faecalis and for antifungal activity against C. albicans. Compound 59 [1-(2,4-dichlorobenzyl)-N- (2-diethylaminoethyl)-1H-benzimidazole-5-carboxamidine], with a
[...] Read more.
A series of 22 novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5- carboxamidine derivatives were synthesized and evaluated for in vitro antibacterial activity against S. aureus and methicillin resistant S. aureus (MRSA), E. coli, E. faecalis and for antifungal activity against C. albicans. Compound 59 [1-(2,4-dichlorobenzyl)-N- (2-diethylaminoethyl)-1H-benzimidazole-5-carboxamidine], with a 3,4-dichlorophenyl group at the C-2 position, displayed the greatest activity (MIC = 3.12 μg/mL against both some bacteria and the fungus C. albicans). Full article
Open AccessArticle N,N’-Substituted 1,2,5 Thiadiazolidine 1,1-Dioxides: Synthesis, Selected Chemical and Spectral Proprieties and Antimicrobial Evaluation †
Molecules 2005, 10(11), 1387-1398; doi:10.3390/10111387
Received: 28 June 2005 / Revised: 5 September 2005 / Accepted: 10 September 2005 / Published: 30 November 2005
Cited by 15 | PDF Full-text (96 KB) | HTML Full-text | XML Full-text
Abstract
The sulfamide functional group is increasingly relevant in both medicinal and bioorganic chemistry. We report here practical access to a series of N2,N5-substituted five-membered cyclosulfamides. The five-membered heterocyclic motif was prepared starting from proteogenic amino acids and chlorosulfonyl isocyanate via the Mitsunobu reaction.
[...] Read more.
The sulfamide functional group is increasingly relevant in both medicinal and bioorganic chemistry. We report here practical access to a series of N2,N5-substituted five-membered cyclosulfamides. The five-membered heterocyclic motif was prepared starting from proteogenic amino acids and chlorosulfonyl isocyanate via the Mitsunobu reaction. Selected chemical and spectral proprieties and the antimicrobial evaluation of these compounds are detailed. Full article
Open AccessArticle Synthesis, Reactivity and Biological Activity of Novel Bisbenzofuran-2-yl-Methanone Derivatives
Molecules 2005, 10(11), 1399-1408; doi:10.3390/10111399
Received: 4 August 2005 / Revised: 11 October 2005 / Accepted: 15 October 2005 / Published: 30 November 2005
Cited by 15 | PDF Full-text (93 KB) | HTML Full-text | XML Full-text
Abstract
Preparation of bisbenzofuran-2-yl-methanone (1), the corresponding ketoxime 4, semicarbazone and thiosemicarbazone 3a and 3b, ether derivatives of the ketoximes 5a-j and the alcohol 2 are described. These substances have been prepared in excellent yields. All the synthesized compounds except 5i have been tested
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Preparation of bisbenzofuran-2-yl-methanone (1), the corresponding ketoxime 4, semicarbazone and thiosemicarbazone 3a and 3b, ether derivatives of the ketoximes 5a-j and the alcohol 2 are described. These substances have been prepared in excellent yields. All the synthesized compounds except 5i have been tested against five different microorganisms and some of them were found to be active against some of the species studied. Full article
Open AccessArticle Facile Microwave-assisted Synthesis of 9,10-Dihydro-9,10-ethanoanthracene-11-carboxylic acid Methyl Ester
Molecules 2005, 10(11), 1409-1412; doi:10.3390/10111409
Received: 16 August 2005 / Revised: 19 August 2005 / Accepted: 23 August 2005 / Published: 30 November 2005
Cited by 5 | PDF Full-text (119 KB) | HTML Full-text | XML Full-text
Abstract A facile, high yielding synthesis of 9,10-dihydro-9,10-ethano- anthracene-11- carboxylic acid methyl ester using a modified commercial domestic microwave oven is reported. Full article
Open AccessArticle Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester
Molecules 2005, 10(11), 1413-1418; doi:10.3390/10111413
Received: 25 August 2005 / Revised: 22 September 2005 / Accepted: 23 September 2005 / Published: 30 November 2005
Cited by 5 | PDF Full-text (54 KB) | HTML Full-text | XML Full-text
Abstract
A simple and efficient method for the preparation of 1-methyl-3-oxo-7- oxabicyclo[2.2.1]hept-5-en-2-carboxylic acid methyl ester (1) is described. The first step is a highly regioselective Diels-Alder reaction between 2-methylfuran and methyl-3-bromo- propiolate. A remarkably difficult ketal hydrolysis reaction was effected by treatment with HCl,
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A simple and efficient method for the preparation of 1-methyl-3-oxo-7- oxabicyclo[2.2.1]hept-5-en-2-carboxylic acid methyl ester (1) is described. The first step is a highly regioselective Diels-Alder reaction between 2-methylfuran and methyl-3-bromo- propiolate. A remarkably difficult ketal hydrolysis reaction was effected by treatment with HCl, a simple reagent that was shown to be more efficient, in this case, than commonly used more elaborate methods. Full article
Open AccessArticle Reaction of Thallium(III) Salts with Homoallylic Alcohols: Ring Contraction vs. Dimethoxylation
Molecules 2005, 10(11), 1419-1428; doi:10.3390/10111419
Received: 24 March 2005 / Revised: 26 July 2005 / Accepted: 26 July 2005 / Published: 30 November 2005
Cited by 6 | PDF Full-text (97 KB) | HTML Full-text | XML Full-text
Abstract
The oxidation of 2-(3,4-dihydronaphthalen-1-yl)-ethanol (1) with a variety ofthallium(III) salts was investigated. An indan, formed by a ring contraction reaction, wasobtained in good to moderate yields under a variety of reaction conditions: i) thalliumtriacetate (TTA) in aqueous AcOH; ii) thallium tris-trifluoroacetate (TTFA) in
[...] Read more.
The oxidation of 2-(3,4-dihydronaphthalen-1-yl)-ethanol (1) with a variety ofthallium(III) salts was investigated. An indan, formed by a ring contraction reaction, wasobtained in good to moderate yields under a variety of reaction conditions: i) thalliumtriacetate (TTA) in aqueous AcOH; ii) thallium tris-trifluoroacetate (TTFA) in aqueousTFA; iii) TTFA in CH2Cl2; iv) thallium tripropionate (TTP) in aqueous propionic acidand v) thallium tris-[(S)-(-)-triacetoxypropionate] in aqueous (S)-(-)-2-acetoxypropionicacid. On the other hand, the reaction of compound 1 with TTA in methanol led to a 2:1mixture of the corresponding cis- and trans-dimethoxylated compounds, respectively.These compounds were formed by a thallium-promoted addition of methanol to thedouble bond. Full article

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