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353 KiB

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Bioactivity of a Family of Chiral Nonracemic Aminobenzylnaphthols towards Candida albicans

by Maria Annunziata M. Capozzi, Cosimo Cardellicchio, Angela Magaletti, Antonio Bevilacqua, Marianne Perricone and Maria Rosaria Corbo

Molecules 2014, 19(4), 5219-5230; https://doi.org/10.3390/molecules19045219 - 23 Apr 2014

Cited by 12 | Viewed by 5050

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 [...] Read more.

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)

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343 KiB

Open AccessArticle

Parallel Synthesis of 2-Substituted 6-(5-Oxo-1-phenylpyrrolidin-3-yl)pyrimidine-5-carboxamides

by Bojana Črček, Jernej Baškovč, Uroš Grošelj, Drago Kočar, Georg Dahmann, Branko Stanovnik and Jurij Svete

Molecules 2012, 17(5), 5363-5384; https://doi.org/10.3390/molecules17055363 - 08 May 2012

Cited by 5 | Viewed by 4988

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, [...] Read more.

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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741 KiB

Open AccessArticle

Parallel Synthesis of Peptide-Like Macrocycles Containing Imidazole-4,5-dicarboxylic Acid

by Zhigang Xu, Kraig A. Wheeler and Paul W. Baures

Molecules 2012, 17(5), 5346-5362; https://doi.org/10.3390/molecules17055346 - 08 May 2012

Cited by 4 | Viewed by 5487

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 [...] Read more.

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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473 KiB

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Synthesis of Amino Core Compounds of Galactosyl Phytosyl Ceramide Analogs for Developing iNKT-Cell Inducers

by Yin-Cheng Huang, Li-Wu Chiang, Kai-Shiang Chang, Wen-Chin Su, Yi-Hsian Lin, Kee-Ching Jeng, Kun-I Lin, Kuo-Yen Liao, Ho-Lein Huang and Chung-Shan Yu

Molecules 2012, 17(3), 3058-3081; https://doi.org/10.3390/molecules17033058 - 12 Mar 2012

Cited by 4 | Viewed by 5930

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 [...] Read more.

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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