Synthesis and evaluation of N-alkyl-β-d-glucosylamines on the growth of two wood fungi, Coriolus versicolor and Poria placenta

Muhizi, Théoneste; Coma, Véronique; Grelier, Stéphane

doi:10.1016/j.carres.2008.07.005

Cited by 22 publications

(16 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The peaks at 95.6 and 91.7 ppm were assigned to C1 of glucose α- and β-anomers, respectively. Hence, the –NH 2 group was attached on C1 in the product, which has been identified to be β- d -glucopyranosylamine according to the literature . Without a catalyst, the formation of the amino sugar in ammonia solution required several days at the same temperature .…”

Section: Results and Discussionmentioning

confidence: 99%

“…Hence, the −NH 2 group was attached on C1 in the product, which has been identified to be β-Dglucopyranosylamine according to the literature. 53 Without a catalyst, the formation of the amino sugar in ammonia solution required several days at the same temperature. 54 For comparison, the ESI spectra of glucose with AMT and Na 2 WO 4 under identical conditions were examined (see Figure S6 Model Compound Experiments.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

See 1 more Smart Citation

One-Step Synthesis of N-Heterocyclic Compounds from Carbohydrates over Tungsten-Based Catalysts

Chen

Yang

Hülsey

et al. 2017

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

A one-step reaction system has been developed to convert glucose and other renewable carbohydrates into important N-heterocyclic compounds in ammonia solution. Under optimal conditions, 2-methyl pyrazine (MP) and 4(5)-methyl imidazole (MI) were produced within 15 min with combined yields of around 40%. While the formation of 4(5)-MI was identified as a noncatalytic process, the yield of 2-MP was highly influenced by the presence of catalysts. In particular, nearly 3-fold yield enhancement of 2-MP was achieved over several tungsten-based catalysts. Control experiments, isotope-labeling tests, ESI-MS, and NMR analysis revealed that the formation of 2-MP follows a fragmentation mechanism, while small tungsten clusters such as [HW2O7]− and [W4O13]2– were the catalytically active species facilitating both glucose fragmentation and the subsequent cyclization reaction to generate pyrazine rings. The work exemplifies the possibility of sustainable production of important N-containing, heterocyclic chemicals from woody biomass, where the identification and understanding of novel catalysts are the key.

show abstract

Section: Results and Discussionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

One-Step Synthesis of N-Heterocyclic Compounds from Carbohydrates over Tungsten-Based Catalysts

Chen

Yang

Hülsey

et al. 2017

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

show abstract

“…The combination of two physiological effects in a hybrid molecule is intended to produce a synergistic effect (increased efficacy) in the treatment of a disease or disorder. For example, the introduction of carbohydrate fragments into the structure of physiologically active substances not only increases their water solubility, but also significantly reduces toxicity, which makes it possible to recommend the method of glycosylation of a physiologically active compound at the glycosidic center of sugars as one of the possible ways to obtain low-toxic drugs [10][11][12][13][14][15][16][17][18][19][20]. It is also known that carbohydrates in the form of various derivatives are part of the cells of any living organism, playing here the role of a structural material, a supplier of energy, substrates and regulators of specific and biochemical processes.…”

Section: Resultsmentioning

confidence: 99%

Hybrid Molecules Based on Alkaloids

Нуркенов¹,

Фазылов²,

Minayeva³

et al. 2021

Chem. J. of Kaz.

View full text Add to dashboard Cite

This review has been summarized the data on the synthesis of new hybrid derivatives based on alkaloid molecules. At the same time, there have been analyzed methods for obtaining hybrid structures containing fragments of natural compounds molecules in combination with other biologically active plant metabolites, as leading compounds for the development of new pharmacologically valuable agents, with the aim of creating new original drugs. The combination of pharmacophoric residues in one molecule, namely various aromatic and heterocyclic substituents in the nucleoside position of natural alkaloids, opens up new possibilities for both the subsequent chemical modification of the polyfunctional derivatives obtained and their new diverse biological activity. Effective methods of synthesis have been developed on the basis of directed transformations of these compounds (or their precursors). A wide range of pharmaco-logical properties of combined compounds of these series with a combination of low toxicity is promising. Considering that the preparation of combined derivatives based on alkaloid molecules has been insufficiently studied, the targeted synthesis of new com-pounds is of interest both in terms of new medicinespreparation and the development of new methods of organic synthesis, as well as the molecules stereochemistry determination of a new series of compounds.

show abstract

“…Mycelial growth assay: The antifungal activity of compounds was evaluated by the mycelial growth assay [20][21][22] , conducted on PDA medium. Prior to the fungal inoculation, 100 µL of different concentrations of the tested compounds were poured and spread on the surface of the agar medium.…”

Section: Methodsmentioning

confidence: 99%

Inhibitory Activities of Griseofulvin and Its Analogues against Phytopathogenic Fungi

Zhu¹,

ZhiZhen²,

Yu³

et al. 2013

Asian J. Chem.

View full text Add to dashboard Cite

The antifungal activity of griseofulvin was evaluated against phytopathogenic fungi including Fusarium moniliforme, Fusarium solani, Fusarium oxysporum and Colletotrichum truncatum. The greenhouse test was also made to evaluate the control efficiency of griseofulvin to eggplant powdery mildew. The results indicated griseofulvin could not only obviously inhibit fungi in laboratory experiments but efficiently control eggplant powdery mildew in greenhouse test. Subsequently, five griseofulvin analogues were synthesized and evaluated for antifungal activities against the four fungi. The results showed that these compounds performed significantly different activities in comparison with griseofulvin. The inhibition mechanism and bioavailability of active analogues were taken to expound their different performance and relations of structure and activity. The solubility in different solvents of analogues and griseofulvin was roughly evaluated and compared.

show abstract

Synthesis and evaluation of N-alkyl-β-d-glucosylamines on the growth of two wood fungi, Coriolus versicolor and Poria placenta

Cited by 22 publications

References 45 publications

One-Step Synthesis of N-Heterocyclic Compounds from Carbohydrates over Tungsten-Based Catalysts

One-Step Synthesis of N-Heterocyclic Compounds from Carbohydrates over Tungsten-Based Catalysts

Hybrid Molecules Based on Alkaloids

Inhibitory Activities of Griseofulvin and Its Analogues against Phytopathogenic Fungi

Contact Info

Product

Resources

About