N-Glucosides of Aminobenzoic Acids and Aminophenols

Kublashvili, R. I.

doi:10.1023/b:conc.0000018115.15793.d5

Cited by 9 publications

(6 citation statements)

References 7 publications

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“…4,5 Interest in the study of glucosylamines has grown over the years due to their widespread uses. These compounds not only constitute starting materials for the synthesis of different amino bioactive compounds, 6,7 but also can be used without any modification in various other applications. According to Stan et al, 8 Nalkyl glucosylamines can be used as gelators for various organic liquids.…”

Section: Introductionmentioning

confidence: 99%

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

Muhizi

Coma

Grelier

2008

Carbohydrate Research

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Section: Introductionmentioning

confidence: 99%

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

Muhizi

Coma

Grelier

2008

Carbohydrate Research

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“…Furthermore, the yield of product was increased to 58%. This is a satisfactory result because it is well-known that electron-rich amines give very poor yields (13−30%) of N -glycosyl compounds when conventional heating methods are used. , …”

Section: Chemistrymentioning

confidence: 90%

“…This is a satisfactory result because it is well-known that electron-rich amines give very poor yields (13-30%) of N-glycosyl compounds when conventional heating methods are used. 21,24 To our knowledge, this is the first application of the use of microwave heating in the condensation of sugars with anilines. This satisfactory synthetic result prompted us to verify the generality of the method.…”

Section: Chemistrymentioning

confidence: 98%

“…Few synthetic methods have been reported for the preparation of N -arylglycosylamines starting from aniline derivatives. − Usually, the reaction could be accomplished by heating in protic solvents for different periods of time. The N -arylglycosylamines were isolated in poor to good yield depending on the reactivity of the aniline derivative.…”

Section: Chemistrymentioning

confidence: 99%

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3-Demethoxy-3-glycosylaminothiocolchicines: Synthesis of a New Class of Putative Muscle Relaxant Compounds

Gelmi¹,

Pocar²,

Pontremoli³

et al. 2006

J. Med. Chem.

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A novel class of 3-demethoxy-3-glycosylaminothiocolchicines (7) was prepared and tested for muscle relaxant activity. The syntheses were performed starting from the new 3-amino-3-demethoxythiocolchicine (5) prepared in good yield from 3-O-demethylthiocolchicine (1c) using the Buchwald-Hartwig reaction. The condensation of 5 with a series of pentose and hexose sugars (6) gave a series of 3-demethoxy-3-glycosylaminothiocolchicines (7). Their preparation was accomplished by adapting and improving a previous procedure for the preparation of N-arylglycosylamines. In particular, replacing traditional heating with microwave irradiation represents the key improvement of the process. The biological activity of the 3-demethoxy-3-glycosylaminothiocolchicines (7) was evaluated on GABA and strychnine-sensitive glycine receptors present in rat brain and spinal cord.

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“…Wang and his co-worker [104] prepared a number of N-glycopyranosylamines by condensation of p-aminobenzoic acid with penta-and hexapyranoses in ethanol/water (5:1), using acetic acid at 0°C (entry1), as a result peracetyl derivatives were formed but with αor -anomer. Kublashvili group [105] followed the same conditions but along with p-aminobenzoic they also used o-and m-aminobenzoic acids and treated with D-sugars and obtained a mixture of αand -anomers in each case Another group.Qian and collaborators [106] then work on it and synthesize N-arylglycosylamines using different type of sugars such that D-glucose, D-galactose, D-mannose, and D-xylose by reacting it with fluorinated anilines, in presence of water and a small amount of hydrochloric acid (entry 2). And as a consequence, all compounds were formed with -configuration stereospecifically.…”

Section: (D) Replacing a Hydroxyl Group Of Unprotected Sugar By N-conmentioning

confidence: 99%

An Overview on the ChemicalN‐Functionalization of Sugars and Formation ofN‐Glycosides

2020

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Its even more than a centennial that the systematic researches of chemical alteration of sugars have been advancing. Out of all the interest in the field of N‐glycoside has assembled pace over the past few years. Therefore, N‐functionalization of sugar is one of the most fundamental modifications along with other group like azide, amide etc also play a remarkable role in the field of glycoscience. Different approaches to access structurally modified N‐glycosides in carbohydrate derivatives are reviewed. The goal of this review is to provide an overview of different way of N‐functionalization of amino sugar and induction of nitrogen scaffolds for the synthesis of various orthogonal protective groups of the N‐glycoside. The N‐functionalization of sugars designate as follows: (a) glycosylamine, (b) glycosyl azide, and (c) introduction of N‐functionality to the sugar for formation of N‐glycosides. This is the first review focus on N‐functionalization of sugars which will be a future scope that influence the readers to work in this area further.

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N-Glucosides of Aminobenzoic Acids and Aminophenols

Cited by 9 publications

References 7 publications

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

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

3-Demethoxy-3-glycosylaminothiocolchicines: Synthesis of a New Class of Putative Muscle Relaxant Compounds

An Overview on the ChemicalN‐Functionalization of Sugars and Formation ofN‐Glycosides

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