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Special Issue "Parallel Synthesis"

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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 March 2012)

Special Issue Editor

Guest Editor
Dr. Alexander Stadler

Anton Paar GmbH, Anton-Paar-Str. 20, 8054 Graz, Austria
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Published Papers (4 papers)

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Research

Open AccessArticle Bioactivity of a Family of Chiral Nonracemic Aminobenzylnaphthols towards Candida albicans
Molecules 2014, 19(4), 5219-5230; doi:10.3390/molecules19045219
Received: 20 February 2014 / Revised: 8 April 2014 / Accepted: 16 April 2014 / Published: 23 April 2014
PDF Full-text (353 KB) | HTML Full-text | XML Full-text
Abstract
Chiral nonracemic aminobenzylnaphthols were obtained by a Betti multi-component reaction between 2-naphthol, aryl aldehydes and enantiopure arylethylamine. Moreover, some new aminobenzylnaphthols were synthesized by a similar reaction between 2-naphthol, aryl aldehydes and prolinol. These aminobenzylnaphthols, synthesized from different components and thus having different
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Chiral nonracemic aminobenzylnaphthols were obtained by a Betti multi-component reaction between 2-naphthol, aryl aldehydes and enantiopure arylethylamine. Moreover, some new aminobenzylnaphthols were synthesized by a similar reaction between 2-naphthol, aryl aldehydes and prolinol. These aminobenzylnaphthols, synthesized from different components and thus having different structural features, were tested as anti-yeast agents inhibiting Candida albicans. The effect towards the test strain was studied with a microdilution approach and three different concentrations (150, 300 and 450 µg/mL) were tested. The best results were found for the aminobenzylnaphthols obtained from 1-naphthylethylamine and from natural prolinol. The use of the two-way ANOVA highlighted the better performances of the prolinol derivative among the differently structured aminobenzylnaphthols that were screened. The activity towards C. albicans of this prolinol derivative resulted to be interesting and could represent a promising alternative to overcome the problem of the strains resistant to the traditional antifungals. Full article
(This article belongs to the Special Issue Parallel Synthesis)
Open AccessArticle Parallel Synthesis of Peptide-Like Macrocycles Containing Imidazole-4,5-dicarboxylic Acid
Molecules 2012, 17(5), 5346-5362; doi:10.3390/molecules17055346
Received: 5 April 2012 / Revised: 26 April 2012 / Accepted: 3 May 2012 / Published: 8 May 2012
Cited by 2 | PDF Full-text (741 KB) | Supplementary Files
Abstract
We prepared a series of peptide-like 14-membered macrocycles containing an imidazole-4,5-dicarboxylic acid scaffold by using known coupling reagents and protecting group strategies. Yields of the purified macrocycles were poor on average, yet seemingly independent of amino acid substitution or stereochemistry. The macrocycles retain
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We prepared a series of peptide-like 14-membered macrocycles containing an imidazole-4,5-dicarboxylic acid scaffold by using known coupling reagents and protecting group strategies. Yields of the purified macrocycles were poor on average, yet seemingly independent of amino acid substitution or stereochemistry. The macrocycles retain some level of conformational variability as observed by both molecular modeling and X-ray crystallography. These macrocycles represent a new class of structures for further development and for future application in high-throughput screening against a variety of biological targets. Full article
(This article belongs to the Special Issue Parallel Synthesis)
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Open AccessArticle Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides
Molecules 2012, 17(5), 5363-5384; doi:10.3390/molecules17055363
Received: 20 March 2012 / Revised: 24 April 2012 / Accepted: 26 April 2012 / Published: 8 May 2012
Cited by 4 | PDF Full-text (343 KB)
Abstract
A library of 24 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides 10{1,2; 1–12} was prepared by a parallel solution-phase approach. The synthesis comprises a five-step transformation of itaconic acid (11) into 1-methyl and 1-phenyl substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxylic acids 17{1,
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A library of 24 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides 10{1,2; 1–12} was prepared by a parallel solution-phase approach. The synthesis comprises a five-step transformation of itaconic acid (11) into 1-methyl and 1-phenyl substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxylic acids 17{1,2} followed by parallel amidation of 17{1,2} with a series of 12 aliphatic amines 18{1–12} to afford the corresponding carboxamides 10 in good overall yields and in 80–100% purity. Full article
(This article belongs to the Special Issue Parallel Synthesis)
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Open AccessArticle Synthesis of Amino Core Compounds of Galactosyl Phytosyl Ceramide Analogs for Developing iNKT-Cell Inducers
Molecules 2012, 17(3), 3058-3081; doi:10.3390/molecules17033058
Received: 20 January 2012 / Revised: 1 March 2012 / Accepted: 6 March 2012 / Published: 12 March 2012
Cited by 4 | PDF Full-text (473 KB) | Supplementary Files
Abstract
1-Aminophytosphingosine and 6-aminogalactosyl phytosphingosine were prepared in 61% and 40% yield libraries with 44 carboxylic acids showed that a 4-butylbenzoic acid-derived product exe, respectively. Glycosylation using benzoyl-protected lipid resulted in better a-selectivity for ceramide analogs, but the yield was less than that obtained
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1-Aminophytosphingosine and 6-aminogalactosyl phytosphingosine were prepared in 61% and 40% yield libraries with 44 carboxylic acids showed that a 4-butylbenzoic acid-derived product exe, respectively. Glycosylation using benzoyl-protected lipid resulted in better a-selectivity for ceramide analogs, but the yield was less than that obtained with benzyl moieties. Screening the amide rted less cytotoxicity. These analogs were purified for validation of immunological potencies and the a-GalCer analog but not the sphingosine analog stimulated human iNKT cell population. Full article
(This article belongs to the Special Issue Parallel Synthesis)
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