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Synthesis of migrastatin analogues as inhibitors of tumour cell migration: Exploring structural change in and on the macrocyclic ring
(Wiley, 2015-11-04)
Migrastatin and isomigrastatin analogues have been synthesised in order to contribute to structure-activity studies on tumour cell migration inhibitors. These include macrocycles varying in ring size, functionality and ...
Glycoclusters as lectin inhibitors: comparative analysis on two plant agglutinins with different folding as a step towards rules for selectivity
(Elsevier, 2015-09-23)
The emerging physiological significance of carbohydrate (glycan) protein (lectin) recognition engenders the interest to design synthetic inhibitors with a high level of selectivity among natural sugar receptors. Plant ...
Allylic azide rearrangement in tandem with Huisgen cycloaddition for stereoselective annulation: synthesis of C-Glycosyl iminosugars
(American Chemical Society, 2015-12-09)
Allylic azide rearrangement is used. in,tandem with. intramolecular azide-alkene cycloaddition to give a triazoline that when subsequently decomposed in the presence of a nucleophile gives piperidines. The tandem reaction ...
Bi- to tetravalent glycoclusters presenting GlcNAc/GalNAc as inhibitors: from plant agglutinins to human macrophage galactose-type lectin (CD301) and galectins
(Royal Society of Chemistry, 2015-02-17)
Emerging insights into the functional spectrum of tissue lectins leads to identification of new targets for the custom-made design of potent inhibitors, providing a challenge for synthetic chemistry. The affinity and ...
Coiled coil type neoglycoproteins presenting three lactose residues
(Elsevier, 2016-02-06)
Scaffold design, synthesis and application are relevant for biomedical research. For example, multivalent interactions, such as those between cell surface glycoproteins and lectins can influence the potency and duration ...
Lewis acid induced anomerization of se-glycosides. Application to synthesis of alpha-Se-GalCer
(American Chemical Society, 2016-01-22)
The TiCl4 induced anomerization of selenium glycosides of galacturonic acid derivatives is reported. The reaction was successful for galacturonic acid when various alkyl, alkenyl, alkynyl, saccharide, steroid, and lipid ...
Synthesis of an orthogonally protected polyhydroxylated cyclopentene from L-Sorbose
(Chemical Editorial Society (ACES) / Wiley, 2016-07-06)
The use of l-sorbose in the synthesis of functionalized cyclopentene derivatives was accomplished. These cyclopentene derivatives are related to those found in naturally occurring jatrophane frameworks and in other bioactive ...
Multivalent carbohydrate-lectin interactions: the way synthetic chemistry enables insights into nanometric recognition
(MDPI Open Access, 2016-05-13)
Glycan recognition by sugar receptors (lectins) is intimately involved in many aspects of cell physiology. However, the factors explaining the exquisite selectivity of their functional pairing are not yet fully understood. ...
Synthesis of iminosugar derivatives presenting naphthyl and alkyl amine interacting groups and binding to somatostatin receptors
(Royal Society of Chemistry, 2014-03-20)
The synthesis of 1-deoxynojirimycin (DNJ) derivatives presenting a 2-naphthylmethyl and an alkyl amino side chain from L-sorbose is described. The synthetic derivatives were tested for their ability to inhibit the binding ...
Synthesis of migrastatin and its macroketone analogue and in vivo FRAP analysis of the macroketone on E-Cadherin dynamics
(Wiley-VCH Verlag, 2014-06-11)
An efficient and scalable synthesis of a key acyclic intermediate used for the preparation of migrastatin and its macroketone analogue is described; Brown alkoxyallylation is the key step for this synthesis. The macroketone ...