Efficient synthesis of coumarin based triazole linked O-glycoconjugates as new bio-active glycohybrids

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2025-01-21 DOI:10.1016/j.carres.2025.109395

Sunil Sharma, Ram Sagar

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引用次数: 0

Abstract

Glycohybrids are biologically significant molecules with variety of biological functions and are found as structural motifs in numerous natural products. Here, we report the synthesis of various new coumarin-based O-glycoconjugates as glycohybrids that are chirally enriched and bridged by 1,2,3-triazoles ring system. The1,2,3-triazoles bridging was done via CuAAC click-chemistry. Click chemistry offers several advantages, including high chemo- and regioselectivity, mild reaction conditions, easy purification, and compatibility with multiple functional groups. Two series of O-glycoconjugates as new glycohybrids were designed and efficiently synthesized in very good isolated yields, using d-glucose, d-galactose, d-mannose, d-arabinose, 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal and 3,4-di-O-acetyl-D-arabinal derived 1-O-propargylated glycosides, reacting with various 4-azidocoumarins under click-chemistry reaction conditions. The prepared new coumarin-based O-glycoconjugates as glycohybrids were found to possess anticancer activity against MCF-7 breast cancer cell lines at micromolar concentration.

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".