94482-21-0Relevant articles and documents
The synthesis and antiviral activity of glycyrrhizic acid conjugates with α-D-glucosamine and some glycosylamines
Kondratenko,Baltina,Mustafina,Vasil'eva,Pompei,Deidda,Plyasunova,Pokrovskii,Tolstikov
, p. 275 - 282 (2004)
Glycyrrhizic acid and its 30-methyl ester were conjugated with 2-amino-1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-glucopyranose, 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl amine, 2,3,4-tri-O-acetyl- α-L-arabinopyranosyl amine, 2-acetamido-2-deoxy-β-D-glucopyranosyl amine, and β-D-galactopyranosyl amine using N,N′- dicyclohexylcarbodiimide and its mixtures with N-hydroxybenzotriazole. Structures of the conjugates were confirmed by IR, UV, 1H, and 13C NMR spectroscopy. The glycoconjugate with the residues of 2-acetamido-2-deoxy-β-D-glucopyranosyl amine in the carbohydrate part of its molecule exhibited antiviral activity (ID50 4 μg/ml) toward the herpes simplex type 1 virus (HSV-1) in the VERO cell culture. Two compounds demonstrated anti-HIV-1 activity (50-70% inhibition of p24) in a culture of MT-4 cells at concentrations of 0.520 μg/ml.
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.
Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations
Sr?an, Laura,Ziegler, Thomas
supporting information, p. 888 - 894 (2020/05/18)
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
Anti-tick-borne encephalitis virus activity of novel uridine glycoconjugates containing amide or/and 1,2,3-triazole moiety in the linker structure
Brzuska, Gabriela,Pastuch-Gawolek, Gabriela,Krawczyk, Monika,Szewczyk, Boguslaw,Krol, Ewelina
, p. 1 - 20 (2020/12/22)
Tick-borne encephalitis virus (TBEV) transmitted by ticks is a pathogen of great medical importance. As still no effective antiviral treatment is available, in the present study, a series of uridine glycoconjugates containing amide or/and 1,2,3-triazole moiety in the linker structure was synthesized and evaluated for the antiviral activity against two strains of TBEV: a highly virulent Hypr strain and less virulent Neudoerfl strain, using standardized previously in vitro assays. Our data have shown that four compounds from the series (18–21) possess strong activity against both TBEV strains. The half maximal inhibitory concentration (IC50) values of compounds 18–21 were between 15.1 and 3.7 μM depending on the virus strain, which along with low cytotoxicity resulted in high values of the selectivity index (SI). The obtained results suggest that these compounds may be promising candidates for further development of new therapies against flaviviruses.
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.
Chemo-selective Rh-catalysed hydrogenation of azides into amines
Galan, M. Carmen,Ghirardello, Mattia,Ledru, Helene,Sau, Abhijit
supporting information, (2020/02/18)
Rh/Al2O3 can be used as an effective chemo-selective reductive catalyst that combines the mild conditions of catalytic hydrogenation with high selectivity for azide moieties in the presence of other hydrogenolysis labile groups such as benzyl and benzyloxycarbonyl functionalities. The practicality of this strategy is exemplified with a range of azide-containing carbohydrate and amino acid derivatives.
Further development of the tin-catalyzed transcarbamoylation reaction
Hasegawa, Tomoyuki,Ichikawa, Yoshiyasu,Masuda, Toshiya,Minami, Takahiro,Morishita, Yukinori,Ochi, Rika,Sato, Hiroshi
supporting information, p. 2373 - 2378 (2020/08/19)
Studies carried out to further develop tin-catalyzed trans-carbamoylation reactions demonstrated that transcarbamoylation of cinnamyl alcohol in the context of allyl cyanate-to-isocyanate rearrangement can be efficiently carried out on a ten-gram scale and that tin-catalyzed transcarbamoylation is a valuable alternative to the method using trichloroacetyl isocyanate. In addition, methyl carbamate was found to be an economical carabamoyl donor in tin-catalyzed transcarbamoylation, which showed broad functional group tolerance and allowed a streamlined workup procedure. Finally, a unique synthetic method was developed for the preparation of carbamate-tethered terpene glycoconjugates.
8-hydroxyquinoline glycoconjugates: Modifications in the linker structure and their effect on the cytotoxicity of the obtained compounds
Krawczyk, Monika,Pastuch-Gawo?ek, Gabriela,Pluta, Aleksandra,Erfurt, Karol,Domiński, Adrian,Kurcok, Piotr
, (2019/11/28)
Small molecule nitrogen heterocycles are very important structures, widely used in the design of potential pharmaceuticals. Particularly, derivatives of 8-hydroxyquinoline (8-HQ) are successfully used to design promising anti-cancer agents. Conjugating 8-HQ derivatives with sugar derivatives, molecules with better bioavailability, selectivity, and solubility are obtained. In this study, 8-HQ derivatives were functionalized at the 8-OH position and connected with sugar derivatives (D-glucose or D-galactose) substituted with different groups at the anomeric position, using copper(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition (CuAAC). Glycoconjugates were tested for inhibition of the proliferation of cancer cell lines (HCT 116 and MCF-7) and inhibition of β-1,4-galactosyltransferase activity, which overexpression is associated with cancer progression. All glycoconjugates in protected form have a cytotoxic effect on cancer cells in the tested concentration range. The presence of additional amide groups in the linker structure improves the activity of glycoconjugates, probably due to the ability to chelate metal ions present in many types of cancers. The study of metal complexing properties confirmed that the obtained glycoconjugates are capable of chelating copper ions, which increases their anti-cancer potential.
Synthesis of biurets: Via TMSNCO addition to 1-aminosugars: Application in the de novo synthesis of dC oxidation products
Tsoulougian, Veronika,Psykarakis, Emmanuel E.,Gimisis, Thanasis
, p. 973 - 981 (2019/02/01)
The reaction between 1-aminosugars and trimethylisocyanate (TMSNCO) was optimised as a one-step synthetic strategy for the synthesis of sugar biurets. This protocol was successfully applied to a number of 1-aminosugars, which exclusively provided the corresponding biurets in 67-99% yields. The new methodology was applied in the de novo synthesis of N1-(2-deoxy-α/β-d-erythro-pentofuranosyl)biuret (dfBU) and N1-(2-deoxy-α/β-d-erythro-pentopyranosyl)biuret (dpBU), two known DNA lesions arising from the hydroxyl radical induced decomposition of 2′-deoxycytidine (dCyd).
The effect of monosaccharides on self-assembly of benzenetricarboxamides
Wang, Jue,Qi, Wenjing,Chen, Guosong
supporting information, p. 587 - 591 (2019/01/04)
The interaction between monosaccharides exhibits an important role in the assembly of monosaccharide-containing molecules. In this work, three common monosaccharides, glucose, galactose and mannose, are employed to investigate the effect of monosaccharide on the self-assembly of benzenetricarboxamide (BTA) core-containing molecules. In the presence of monosaccharides, three benzenetricarboxamide derivatives aggregate into different ordered structures. When alanine linkers are introduced to these molecules between the core and the monosacchride, morphologies of three types of monosaccharide BTAs turned to disordered, meanwhile their structures become similar with the increase of the length of alanine linkers, indicating the disappearance of the monosaccharide effects.
