Synthesis of N-glycoside compounds from phthalimide and 5-nitrobenzimidazole via 1,2-O-sulfinyl derivatives and in vitro cytotoxic activity

Benksim, Abdelhafid; Elhizazi, Said; Lakhrissi, B.; Amine, Mohamed; Cherkaoui, Mohamed; Tounsi, Abdessamad; Wadouachi, Anne

doi:10.1007/s13738-020-01877-3

Cited by 2 publications

(5 citation statements)

References 35 publications

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“…Recently, Benksim et al [74] . described that the reaction of 1,2‐ O ‐sulfinyl derivatives with phthalimide or 5‐nitrobenzimidazole in DMF to product 1,2‐ trans ‐ N ‐glycosylated derivatives.…”

Section: Applications Of N‐glycosidesmentioning

confidence: 99%

“…According to the authors, the compounds 95a/b (Figure 9) exhibit cytotoxic activity interesting against the human cancer cell line (Hep‐2) in vitro , using the MTT. However, better valorization of compounds as potential anticancer agents can be established through the study of the “structure‐activity” relationship and the mechanism of action on one compound active [74] …”

Section: Applications Of N‐glycosidesmentioning

confidence: 99%

“…However, better valorization of compounds as potential anticancer agents can be established through the study of the "structure-activity" relationship and the mechanism of action on one compound active. [74] The biological application of N-glycosides has been advancing in recent years, revealing its great importance in the pharmaceutical industry. [75] Another application is in the formation of surfactants which proved interesting in the chemistry of N-glycosides making them less toxic and being able to be specialized in several sectors of the industry.…”

Section: Medicinal Chemistrymentioning

confidence: 99%

“…(Figure 8). [73] Recently, Benksim et al [74] described that the reaction of 1,2-O-sulfinyl derivatives with phthalimide or 5-nitrobenzimidazole in DMF to product 1,2-trans-N-glycosylated derivatives. According to the authors, the compounds 95a/b (Figure 9) exhibit cytotoxic activity interesting against the human cancer cell line (Hep-2) in vitro, using the MTT.…”

Section: Medicinal Chemistrymentioning

confidence: 99%

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Relevant Advances in the Synthesis and Applications of N‐Glycopyranosides

Guimarães,

de Oliveira Silva,

de Sales Barbosa

et al. 2023

ChemistrySelect

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N‐glycosides are produced when an aglycone is connected, for example, using a glycosylation reaction, to the sugar moiety via linkage of C−N bond at anomeric carbon. N‐glycosides are obtained from different precursors, including glucals, 1‐azido glycosides, glycosyl azide, glycosyl isothiocyanate, 2‐deoxy‐2‐iodo‐N‐glycoside, glycosyl‐1H‐1,2,3‐triazol, and 2‐nitroglucal. The biological relevance of N‐glycopyranosides has drowned attracted the attention of several researchers. The scope of this review covers the literature from 2010 to 2022. Recent advances focused on the natural occurrence, synthesis, mechanism, and pharmacological applications of N‐glycopyranosides are discussed.

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Section: Applications Of N‐glycosidesmentioning

confidence: 99%

Section: Applications Of N‐glycosidesmentioning

confidence: 99%

Section: Medicinal Chemistrymentioning

confidence: 99%

Section: Medicinal Chemistrymentioning

confidence: 99%

See 2 more Smart Citations

Relevant Advances in the Synthesis and Applications of N‐Glycopyranosides

Guimarães,

de Oliveira Silva,

de Sales Barbosa

et al. 2023

ChemistrySelect

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“…This acetylated sugar was further subjected to bromination using a mixture of HBr and acetic anhydride. Brominated sugar derivatives (BS1-BS2) were confirmed through thin layer chromatography and spectral analysis 11,12 . Then amino ethyl esters (AE1-AE5) were synthesized by amino acid in the presence of conc.…”

mentioning

confidence: 98%

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2021

IJPSR

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Carbohydrate-based therapeutics are extremely potent, and many carbohydrate-based drugs are in the stage of preclinical or clinical trials. There is a growing interest in developing carbohydrate analogues for novel drug discovery as most of the recently used carbohydrate drugs display significant pharmacological activities and low toxicity. Also, the search for an antipyretic drug is a never-ending challenge. This research aimed at the development and synthesis of a series of amide-linked sugars (PV1-PV20) by coupling brominated sugars with varying amino acids coupled with nicotinic acid (GP1-GP10). Characterization of the derivatives synthesized was done by Infrared and Nuclear Magnetic Resonance Spectroscopy. These congeners were tested to analyze their antipyretic potential, and eight analogs out of twenty showed significant antipyretic activity. Thus, the carbohydratebased amide derivatives show important action in obstruction and therapy of fever. Further work on these lines may play an important role in maintaining good health at a low cost. INTRODUCTION:Oligosaccharides, carbohydrates and glycoconjugates are demanding ingredients for being alive. They intervene many crucial biological systems by cell-based complex operations which can trigger and assist life to percept developments required for disease related to autoimmune system, inflammation, and organ exclusion. The diversity of carbohydrate structures reflects that functional diversity. Natural and synthetic derivatives of carbohydrates have a good amount of therapeutic potential using them to treat various disorders 1 .

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Synthesis of N-glycoside compounds from phthalimide and 5-nitrobenzimidazole via 1,2-O-sulfinyl derivatives and in vitro cytotoxic activity

Cited by 2 publications

References 35 publications

Relevant Advances in the Synthesis and Applications of N‐Glycopyranosides

Relevant Advances in the Synthesis and Applications of N‐Glycopyranosides

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