41355-50-4Relevant articles and documents
High consistency of structure-based design and X-ray crystallography: Design, synthesis, kinetic evaluation and crystallographic binding mode determination of biphenyl-n-acyl-β-d-glucopyranosylamines as glycogen phosphorylase inhibitors
Fischer, Thomas,Koulas, Symeon M.,Tsagkarakou, Anastasia S.,Kyriakis, Efthimios,Stravodimos, George A.,Skamnaki, Vassiliki T.,Liggri, Panagiota G.V.,Zographos, Spyros E.,Riedl, Rainer,Leonidas, Demetres D.
, (2019)
Structure-based design and synthesis of two biphenyl-N-acyl-β-D-glucopyranosylamine derivatives as well as their assessment as inhibitors of human liver glycogen phosphorylase (hlGPa, a pharmaceutical target for type 2 diabetes) is presented. X-ray crysta
Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations
Sr?an, Laura,Ziegler, Thomas
, p. 888 - 894 (2020)
For investigations on the biological functions of oligosaccharides and peptidomimetics, new asparagine-based mono- and disaccharides containing glycopeptides were prepared in solution. The applicability of two common peptide coupling reagents, using an or
Synthesis of cluster N-glycosides based on a β-cyclodextrin core
Garcia-Lopez, Juan J.,Santoyo-Gonzalez, Francisco,Vargas-Berenguel, Antonio,Gimenez-Martinez, Juan J.
, p. 1775 - 1784 (1999)
A convenient method for the synthesis of β-D-gluco-, β-D-galacto-, 2-acetamido-2-deoxy-β-D-gluco- and α-D-mannopyranosylamine clusters based on cyclomaltoheptaose (β-cyclodextrin) is presented. The synthesis involves: 1) the one-pot synthesis of the acetylated chloroacetyl N-glycoside derivatives of D-glucose, D-galactose, 2-acetamido-2-deoxy-D-glucose and D-mannose from the corresponding glycosyl azides, 2) conversion of the chloroacetyl N-glycosides into their isothiouronium derivatives, then 3) attachment of the N-glycosides onto heptakis(6-deoxy-6-iodo) and heptakis(6-chloroacetamido-6-deoxy) β-cyclodextrin by means of nuoleophilic displacement with caesium carbonate in dimethylformamide, and 4) de-O-acetylation of β-cyclodextrin derivatives. The chloroacetyl N-glycoside derivatives were easily prepared by mild reduction of the azide function by one of two methods : a) by the Staudinger reaction, with nBu3P, and b) with 1,3-propanedithiol, as reducing reagents.
Multicomponent diversity oriented synthesis of multivalent glycomimetics containing hexafluorovaline
Bellucci,Sganappa,Sani,Volonterio
, p. 7630 - 7637 (2015)
The chemoselective introduction of fluorinated moieties into biologically relevant scaffolds is now an established strategy to modulate and to study the properties of molecular leads. In this article we propose, for the first time, the diversity oriented
Synthesis and characterization of thiourea- and urea-linked glycolipids as low-molecular-weight hydrogelators
Mathiselvam, Manoharan,Loganathan, Duraikkannu,Varghese, Babu
, p. 14528 - 14542 (2013)
Novel glycolipids with thiourea- and urea-linkers have been synthesized as low-molecular-weight gelators by reacting glycosyl aminoacetamides with alkyl isothiocyanates and isocyanates. The influence of the linker groups on their self-assembly properties has been studied. A gelation study of the obtained neoglycolipids in various solvents showed that they are good hydrogelators. Urea-linked glycolipids showed better hydrogelating ability as compared to thiourea linked glycolipids. The influence of sugar head group and alkyl chain length on the glycolipid's self-assembly has also been studied. The fibrillar structures of the supramolecular hydrogels have been characterized by scanning electron microscopy (SEM). The thermal properties of the hydrogels formed by urea linked glycolipids have been studied by differential scanning calorimetry (DSC) and VT-NMR. Molecular packing has been studied by small angle (SAXS) and single crystal X-ray diffraction methods. The Royal Society of Chemistry 2013.
Synthesis and antimicrobial activity of some new sugar-based monocyclic β-lactams
Jarrahpour,Shekarriz,Taslimi
, p. 29 - 38 (2004)
The syntheses of some new sugar-based monocyclic β-lactams possessing several other functionalities in addition to the carbohydrate moiety are described. The key step was the Staudinger [2+2] cycloaddition of chiral carbohydrate Schiff base 5 with phthalimidoacetyl chloride to yield the sugar-based monocyclic β-lactam 6 as a single isomer. Treatment of protected β-lactams 6 and 8 with methylhydrazine afforded the free amino β-lactams 9 and 10. Acylation of these free amino β-lactams with benzoyl, phenoxyacetyl, cinnamoyl and phenylacetyl chloride in the presence of pyridine afforded β-lactams 11a-d and 12a-d. Some of these novel β-lactams were found to be active against Staphilococcus citrus, Klebsiella pneumoniae, Escherichia coli and Bacillus subtilis.
Structure based inhibitor design targeting glycogen phosphorylase b. Virtual screening, synthesis, biochemical and biological assessment of novel N-acyl-β-d-glucopyranosylamines
Parmenopoulou, Vanessa,Kantsadi, Anastassia L.,Tsirkone, Vicky G.,Chatzileontiadou, Demetra S.M.,Manta, Stella,Zographos, Spyros E.,Molfeta, Christina,Archontis, Georgios,Agius, Loranne,Hayes, Joseph M.,Leonidas, Demetres D.,Komiotis, Dimitri
, p. 4810 - 4825 (2014)
Glycogen phosphorylase (GP) is a validated target for the development of new type 2 diabetes treatments. Exploiting the Zinc docking database, we report the in silico screening of 1888 N-acyl-β-d-glucopyranosylamines putative GP inhibitors differing only
Synthesis of β-galactosylamides as ligands of the peanut lectin. Insights into the recognition process
Cano, María Emilia,Varela, Oscar,García-Moreno, María Isabel,García Fernández, José Manuel,Kovensky, José,Uhrig, María Laura
, p. 58 - 67 (2017)
The synthesis of mono and divalent β-galactosylamides linked to a hydroxylated chain having a C2 symmetry axis derived from L-tartaric anhydride is reported. Reference compounds devoid of hydroxyl groups in the linker were also prepared from β-galactosylamine and succinic anhydride. After functionalization with an alkynyl residue, the resulting building blocks were grafted onto different azide-equipped scaffolds through the copper catalyzed azide-alkyne cycloaddition. Thus, a family of structurally related mono and divalent β-N-galactopyranosylamides was obtained and fully characterized. The binding affinities of the ligands towards the model lectin PNA were measured by the enzyme-linked lectin assay (ELLA). The IC50 values were significantly higher than that of galactose but the presence of hydroxyl groups in the aglycone chain improved lectin recognition. Docking and molecular dynamics experiments were in accordance with the hypothesis that a hydroxyl group properly disposed in the linker could mimic the Glc O3 in the recognition process. On the other hand, divalent presentation of the ligands led to lectin affinity enhancements.
Stereospecific synthesis of the α- and β-D-glucopyranosyl ureas
Ichikawa,Nishiyama,Isobe
, p. 4200 - 4205 (2001)
A new, one-pot, two-stage procedure for the preparation of the α- and β-D-glucopyranosyl ureas has been developed. Oxidation of glucopyranosyl isocyanides provides glucopyranosyl isocyanates, which can be trapped in situ with amines to afford good yields of glucopyranosyl ureas. Application of this method establishes the successful synthesis of the hitherto unknown N,N′-di-α,α- and α,β-D-glucopyranosyl ureas.
Synthesis of novel N-acyl-β-d-glucopyranosylamines and ureas as potential lead cytostatic agents
Parmenopoulou, Vanessa,Manta, Stella,Dimopoulou, Athina,Kollatos, Nikolaos,Schols, Dominique,Komiotis, Dimitri
, p. 932 - 940 (2016)
Novel classes of acetylated and fully deprotected N-acyl-β-d-glucopyranosylamines and ureas have been synthesized and biologically evaluated. Acylation of the per-O-acetylated β-d-glucopyranosylurea (5), easily prepared via its corresponding phosphinimine derivative, by zinc chloride catalyzed reaction of the corresponding acyl chlorides RCOCl (a-f) gave the protected N-acyl-β-d-glucopyranosylureas (6a-f), in acceptable-to-moderate yields. Subsequent deacetylation of analogues 6a-f under Zemplén conditions afforded the fully deprotected derivatives 7a,b,d,e,f, while the desired urea 7c was formed after treatment of 6c with dibutyltin oxide. All protected and unprotected compounds were examined for their cytotoxic activity in different L1210, CEM and HeLa tumor cell lines and were also evaluated against a broad panel of DΝΑ and RNA viruses. Derivative 7c exhibited cytostatic activity against the three evaluated tumor cell lines (IC50 9-24 μΜ) and might be the basis for the synthesis of structure-related derivatives with improved cytostatic potential. Only analogue 6f weakly but significantly inhibited the replication of parainfluenza-3 virus, Sindbis virus and Coxsackie virus B4 in cell cultures at concentrations of 45-58 μM.
