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 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.
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.
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
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 Isonitrile Derivatives of Diglycerides and Carbohydrates as Intermediates for Multicomponent Ugi Reaction
Cheshkov, D. A.,Khrulev, A. A.,Maslov, M. A.,Morozova, N. G.,Nichugovskiy, A. I.,Perevoshchikova, K. A.
, p. 929 - 938 (2021/08/25)
Abstract: Recently, there has been an increase in interest in multicomponent reactions, mainly due to the possibility of assembling of complex organic molecules in just several steps. Isocyanide is a key reagent for the Ugi multicomponent reaction. Isocyanide exhibits dual properties both electrophilic and nucleophilic. Several ways of formation of isonitrile derivatives are known, but the intramolecular dehydration of formamide is considered to be the main method. In this study, we synthesized isonitrile derivatives of dialkyl glycerol and D-glucose which can serve as new useful blocks for the creation of chemical libraries of lipophilic amines with the carbohydrate residue at their terminal nitrogen atom during the further interaction under the conditions of the multicomponent reactions. Structures of all the synthesized compounds were confirmed by physicochemical analytical methods, and these compounds can be used as blocks for the Ugi multicomponent reaction.
Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II
Fan, Zhanfang,Guo, Chun,Hou, Zhuang,Li, Chuanchao,Lin, Bin,Liu, Yang,Liu, Yichuang,Wang, Yitong,Zhang, Miao
, p. 383 - 390 (2019/12/30)
A series of new carbohydrate-based sulphonamide derivatives were designed, synthesised by employing the so-call ‘sugar-tail’ approach. The compounds were evaluated in vitro against a panel of CAs. Compared to their parent compound p-sulfamoylbenzoic acid, these compounds showed nearly 100-fold improvement in their binding affinities against hCA II in vitro. All of compounds showed great water solubility and the pH value of their water solutions of compounds is 7.0. Such properties are advantageous to make them much less irritating to the eye when applied topical glaucomatous drugs, compared to the relatively highly acidic dorzolamide preparations (pH 5.5). Notably, compounds 7d, 7 g, 7 h demonstrated to topically lower intraocular pressure (IOP) in glaucomatous animals better than brinzolamide when applied as a 1% solution directly into the eye. Low cytotoxicity on human cornea epithelial cell was observed in the tested concentrations by the MTT assay.
