150370-50-6Relevant academic research and scientific papers
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)
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.
Carbohydrate-derived iminium salt organocatalysts for the asymmetric epoxidation of alkenes
Bulman Page, Philip C.,Chan, Yohan,Liddle, John,Elsegood, Mark R.J.
, p. 7283 - 7305 (2017/09/13)
A new family of carbohydrate-based dihydroisoquinolinium salts has been prepared and tested for potential as asymmetric catalysts for the epoxidation of unfunctionalized alkene substrates, providing up to 57% ee in the product epoxides.
Acid-catalysed rearrangement of glycosyl trichloroacetimidates: a novel route to glycosylamines
Larsen, Kim,Olsen, Carl Erik,Motawia, Mohammed Saddik
, p. 383 - 387 (2008/09/19)
A novel route to glycosylamines has been developed. Treatment of glycosyl trichloroacetimidates with TMSOTf under glycosylation conditions, but in the absence of an acceptor, resulted in complete rearrangement of the trichloroacetimidates into the corresp
A new method for the stereoselective synthesis of α- and β-glycosylamines using the Burgess reagent
Nicolaou,Snyder, Scott A.,Nalbandian, Annie Z.,Longbottom, Deborah A.
, p. 6234 - 6235 (2007/10/03)
Although glycosylamines constitute an important group of carbohydrates from the standpoint of biology and medicine, methods for their synthesis typically lack substrate generality and/or result in variable stereoselectivity, especially in complex contexts
New uses for the Burgess reagent in chemical synthesis: Methods for the facile and stereoselective formation of sulfamidates, glycosylamines, and sulfamides
Nicolaou,Snyder, Scott A.,Longbottom, Deborah A.,Nalbandian, Annie Z.,Huang, Xianhai
, p. 5581 - 5606 (2007/10/03)
Although the Burgess reagent (methoxycarbonylsulfamoyltriethylammonium hydroxide, inner salt) has found significant use in chemical synthesis as a dehydrating agent, almost no work has been directed towards its potential in other synthetic applications. As this article will detail, we have found that the Burgess reagent is remarkably effective at accomplishing a number of non-dehydrative synthetic tasks when applied to appropriate substrates, such as the formation of sulfamidates from 1,2-diols or epoxyalcohols, α- and β-glycosylamines from carbohydrates, and cyclic sulfamides from 1,2-aminoalcohols. Beyond delineating the power of these new reaction manifolds, we also describe the construction of a group of alternative Burgess-type reagents that extends the scope of these new reactions even further.
Reductive cyclization of δ-hydroxy nitriles: A new synthesis of glycosylamines
Dorsey, Andrew D.,Barbarow, Jennifer E.,Trauner, Dirk
, p. 3237 - 3239 (2007/10/03)
(Matrix presented) The stereoselective cyclization of δ-hydroxy nitriles to afford N,O-acetals and the application of this reaction toward the synthesis of glycosylamines is described.
Total synthesis of spicamycin
Suzuki, Tamotsu,Suzuki, Sayaka T.,Yamada, Iwao,Koashi, Yoshiaki,Yamada, Kazue,Chida, Noritaka
, p. 2874 - 2880 (2007/10/03)
The first total synthesis of one of the spicamycin congeners, SPM VIII (3), is described. A preliminary model study for construction of the characteristic N-glycoside linkage in spicamycin using tetra-O-benzyl-β-D-mannopyranosylamine (13) and halopurines 5 revealed that Pd-catalyzed conditions successfully provided the coupling products 14 and 15 in good yields. It was also shown that thermal anomerization of the N-glycosides easily occurred, which resulted in the predominant formation of the β-anomer as the thermodynamically favored compound, and the activation energy of anomerization of 15 was estimated to be ca. 30 kcal/mol. The novel aminoheptose unit of spicamycin 6 was prepared stereoselectively by carbon elongation of an acyclic aldehyde, prepared by ring cleavage reaction of a highly functionalized cyclohexane derived from naturally abundant myo-inositol. The Pd-catalyzed coupling reaction of the β-heptopyranosylamine 6 with protected 6-chloropurine 5d, followed by deprotection, provided spicamycin amino nucleoside 2, whose condensation with dodecanoylglycine completed the total synthesis of 3. This study confirmed the proposed unique structure of a novel nucleoside antibiotic.
Pentenyl Mannosides in the Synthesis of N-Acylmannopyranosyl Amides: Conformational Analysis of Intermediates
Rao, C. Srinivas,Ratcliffe, Andrew J.,Fraser-Reid, Bert
, p. 1207 - 1212 (2007/10/02)
The reaction of a pentenyl mannopyranoside with N-bromosuccinimide in the presence of acetonitrile and a carboxylic acid leads to an N-acetyl-N-acyl-α-D-mannopyranosyl imide, the acetyl group being derived from acetonitrile, and the acyl group from the carboxylic acid.The latter can be aromatic or aliphatic as exemplified with a protected aspartic acid from which an α-mannopyranosyl asparagine is obtained.Chemoselective deacetylation can be effected either with sodium methoxide or piperidine depending on whether the other acyl group is aromatic or aliphatic, respectively. 1H NMR data, conformational and molecular mechanics analyses show that the N,N-diacyl derivatives exist in a conformation lying between a B2,5 boat and a 1S5 twist boat.
Generation of α-D-Glucopyranosylacetonitrilium Ions. Concerning the Reverse Anomeric Effect
Ratcliffe, Andrew J.,Fraser-Reid, Bert
, p. 747 - 750 (2007/10/02)
Reaction of the α- and β-anomers of the pent-4-enyl D-glucopyranoside (10) with N-bromosuccinimide in dry acetonitrile generated stereospecifically the α-D-glucopyranosylacetonitrilium ion (5α), which reacts in situ with 2-chlorobenzoic acid to afford the α-imide (8α).The result is in contrast to that predicted by the reverse anomeric effect and previous work on trapping carbohydrate acetonitrilium ions with 2-chlorobenzoic acid.The unusually large J12 7.3 Hz for 1-H of (8α) is rationalised by a substantial flattening of the pyranose ring at C-1 and C-2.Molecular dynamic studies on the model α-imide (12) support a flattened 4C1 conformation.Treatment of imide (8α) with sodium methoxide leads to the α-2-chlorobenzamide (9α), which was substantiated by intependent synthesis of the β-2-chlorobenzamide (9β).
