- ACYLATED ACTIVE AGENTS AND METHODS OF THEIR USE FOR THE TREATMENT OF AUTOIMMUNE DISORDERS
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Disclosed herein are acylated active agents (e.g., acylated catechin polyphenols, acylated carotenoids, acylated mesalamines, acylated sugars, acylated shikimic acids, acylated ellagic acid, acylated ellagic acid analogue, and acylated hydroxybenzoic acids), active agent combinations (e.g., with a second agent that is a fatty acid) and methods of their use, e.g., for modulating an autoimmunity marker or for treating an autoimmune disorder.
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Page/Page column 85; 129
(2019/12/28)
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- Preparation method of substituted benzyl or substituted phenyl beta-D-hexuronic acid glucoside
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The invention relates to the technical field of pharmaceutical and chemical industries, and discloses a preparation method of substituted benzyl or substituted phenyl beta-D-hexuronic acid glucoside.The preparation method comprises the steps of taking hexuronic acid as a raw material, and performing acetylation, selective acyl removal, methyl esterification, bromization, aethrization and alkalinealcoholysis to form substituted benzyl or substituted phenyl beta-hexuronic acid glucoside with a structural formula as follows as shown in the description, wherein n is equal to 0-1; and R is o-, m-or para-hydrogen, nitryl, methoxy or halogen. The method is mild in reaction condition, simple in step and suitable for large-scale preparation, and a reaction reagent is easy to obtain.
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Paragraph 0062; 0067; 0068; 0069
(2018/10/19)
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- First conjugates of the diterpenoid isosteviol and glucuronic acid
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Conjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) and glucuronic acid containing two diterpenoid (ent-beyerane) skeletons joined by a 1,6-hexanedicarboxylate spacer and β-D-glucopyranuronoyl moieties were synthesized for the first time.
- Andreeva,Sharipova,Strobykina,Kataev
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p. 465 - 469
(2014/08/18)
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- Sweet anion receptors: Recognition of chiral carboxylate anions by d-glucuronic-acid-decorated diindolylmethane
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Anion receptors containing glucuronic acid were synthesized, and their anion binding ability studied. Chirality of anionic guests derived from mandelic acid and amino acids can be distinguished not only in terms of stability constants but also by signific
- Granda, Jaroslaw M.,Jurczak, Janusz
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supporting information
p. 4730 - 4733
(2013/10/08)
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- Synthesis of some novel D-glucuronic acid acetylated derivatives as potential anti-tumor agents
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A structurally diverse series of Δ4,5-uronamide derivatives have been chemically synthesized starting from D-glucuronic acid itself by means of acetylation, activation, amide bond formation and base-catalyzed elimination protocols. Structure el
- El-Nezhawy, Ahmed O.H.,Adly, Frady G.,Eweas, Ahmed F.,Hanna, Atef G.,El-Kholy, Yehya M.,El-Sayed, Shahenaz H.,El-Naggar, Tarek B.A.
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experimental part
p. 648 - 657
(2012/06/29)
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- Synthesis and surface-active properties of uronic amide derivatives, surfactants from renewable organic raw materials
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Short chemical syntheses were developed to produce a new set of surfactants from uronic acids derived from widely available raw materials. Three different strategies were used to synthesize uronic amide derivatives, the structures of which were totally characterized by spectrometric methods (IR, MS, 1H-RMN and 13C-RMN). The best one, using an acid chloride as the synthetic intermediate, furnished the expected amides as a mixture of anomers in 46-58% global yield. Surface-active properties (CMC, γcmc, Γmax, A min) of homologous series of uronic acid N-alkylamides from C8 to C18 were also assessed. In general, these sugar-based surfactants exhibited good surface-activities, and appeared as valuable nonionic surfactants compared to octylphenol 9-10 ethylene oxide condensate, the most well-known nonionic surfactant. Increasing the alkyl chain length influenced the CMC values for both glucuronic and galacturonic N-alkylamide derivatives. The galacturonic N-alkylamides decreased γcmc at slower values than their counterpart's glucuronic N-alkylamides.
- Laurent, Pascal,Razafindralambo, Hary,Wathelet, Bernard,Blecker, Christophe,Wathelet, Jean-Paul,Paquot, Michel
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experimental part
p. 51 - 63
(2012/01/13)
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- Synthesis of thioesters from carboxylic acids via acyloxyphosphonium intermediates with benzyltriethylammonium tetrathiomolybdate as the sulfur transfer reagent
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(Chemical Equation Presented) An efficient protocol is reported for the synthesis of thioesters from carboxylic acids with use of acyloxy phosphonium salts as intermediates and benzyltriethyl-ammonium tetrathiomolybdate as the sulfur transfer reagent.
- Gopinath, Purushothaman,Vidyarini, Ravindran Sasitha,Chandrasekaran, Srinivasan
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body text
p. 6291 - 6294
(2009/12/08)
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- Synthesis and structural analysis of the anilides of glucuronic acid and orientation of the groups on the carbohydrate scaffolding
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The synthesis of anilides derived from glucuronic acid is described. Secondary anilides had a Z configuration in the solid state and showed intramolecular and intermolecular hydrogen bonding. However, on the basis of NMR and IR studies, there was generall
- Tosin, Manuela,O'Brien, Colin,Fitzpatrick, Geraldine M.,Mueller-Bunz, Helge,Glass, W. Kenneth,Murphy, Paul V.
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p. 4096 - 4106
(2007/10/03)
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- 1,2,3,4-Tetra-O-acetyl-β-D-gluco-pyranuronic acid monohydrate at 120 K and anhydrous 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose at 292 K
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The structure of the title acid as the monohydrate, C14H 18O11·H2O, displays hydrogen bonding which connects the molecules in layers parallel to (101). In the anhydrous glucopyranose, C14H20O10, only chain connectivity is attained but, due to disorder of the OH group, only partially and in two modes, one less favoured than the other. This provides incomplete connectivity between molecules in corrugated layers parallel to (010).
- Baddeley, Thomas C.,Howie, R. Alan,Skakle, Janet M.S.,Wardell, James L.
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p. o711-o714
(2007/10/03)
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- Design, Synthesis, and Evaluation of a Liposaccharide Drug Delivery Agent: Application to the Gastrointestinal Absorption of Gentamicin
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The design, synthesis, and evaluation of a liposaccharide (11) for use as an agent to enhance the gastrointestinal absorption of charged, hydrophilic drugs with poor membrane permeability is reported. 11 was designed to possess both surfactant and ion-pairing properties and was conveniently synthesized from D-glucuronic acid (2) and N-Boc-lipoamino acid (5) precursors in eight steps in good yield. Isothermal titration microcalorimetry was used to determine the critical micelle concentration of 11 (in PBS) to be 2.09 ± 0.01 mM with an enthalpy of demicellization of 4.91 ± 0.11 kJ/mol. The ability of 11 to enhance the gastrointestinal absorption of the aminoglycoside antibiotic gentamicin (1), a hydrophilic polycation with negligible oral bioavailability, was assessed in vivo using rats. Rats dosed orally with a mixture of 11 (100 mg/kg) and 1 (60 mg/kg) had a statistically significant (P ≤ 0.034) increase in Cmax, AUC120, and percent absolute bioavailability (F) compared to control 1 (60 mg/kg) alone. The highest bioavailability (F = 9.1 ± 2.0%) was achieved by dosing with the mixture 11 (100 mg/kg) and 1 (15 mg/kg). This represents a 6-fold increase in bioavailability compared to the control (F = 1.4 ± 0.3%). These results suggest that the molar ratio of 1:11 may be critical in optimizing the delivery system, a finding ascribed in part to the ion-pairing properties of 11. The effect of 11 on the gastrointestinal mucosa was assessed using light microscopy to examine tissue samples from rats used in the pharmacokinetic study. No morphological changes were found in either the esophagi or duodena of the rats examined. One rat dosed with 11 (100 mg/kg) and 1 (60 mg/kg) exhibited slight gastric erosion, which could be attributed to 11.
- Ross, Benjamin P.,DeCruz, Shaun E.,Lynch, Thomas B.,Davis-Goff, Karen,Toth, Istvan
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p. 1251 - 1258
(2007/10/03)
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- Ethyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate
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The crystal structure, at 120 K, and solution 1H and 13C NMR spectra of ethyl 1,2,3,4-tetra-O-acetyl-β-D- glucopyranuronate, (8) have been determined. Compound 8 crystallizes in the triclinic space group, P1(Z = 1) with a = 6.0209(3) A, b = 8.9698(5) A, c = 9.9818(8) A, α = 104.965(2)°, β= 98.522(3)°, γ = 106.790(5)°. The Cremer and Pople puckering parameters [Q = 0.602(4) A, θ = 7.1(4)°, φ = 325(3)°] for the pyranose ring in the solid state indicate a near ideal 4C1 chair conformation with a slight distortion in the direction towards 0H5. A number of weak, soft intermolecular C-H ... O hydrogen bonds set up a 3D array. NMR spectra and FAB and EIMS data have been obtained. Solution NMR parameters suggest that the solid state conformation is maintained in solution in chloroform.
- Baddeley, Thomas C.,Davidson, Iain G.,Skakle, Janet M. S.,Wardell, James L.
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- Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group
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(graph presented) Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN3/SnCl4 or ROH/SnCl4 gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the α-configuration.
- Tosin, Manuela,Murphy, Paul V.
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p. 3675 - 3678
(2007/10/03)
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- Synthesis of 5-fluoro-β-D-glucopyranosyluronic acid fluoride and its evaluation as a mechanistic probe of Escherichia coli β-glucuronidase
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Synthesis of the potential mechanism-based inactivator of β-D-glucuronidases (5-fluoro-β-D-glucopyranosyluronic acid fluoride) was accomplished via a six-step process from D-glucuronic acid that involved radical bromination at C-5 and displacement of the
- Wong,He,Withers
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p. 510 - 518
(2007/10/03)
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- Synthesis and acid-catalyzed hydrolysis of some 3-(4-methoxyphenyl)propyl glucuronates
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3-(4-Methoxyphenyl)propyl D-glucuronate, 3-(4-methoxyphenyl)propyl methyl 4-O-methyl-α-Dglucopyranosiduronate, 3-(4-methoxyphenyl)propyl 1,2,3,4-tetra-O-acetyl-α-D-glucopyranuronate and 3-(4-methoxyphenyl)propyl 1,2-(S):3,5-di-O-benzylidene-α-D-glucofuranuronate were prepared as a model substances for the ester lignin-saccharide bonds. Rates of acid-catalyzed hydrolysis of the prepared compounds in 1 M HCl in acetonitrile-water 3 : 1 at 20 °C have been measured by LC-DAD analysis and it showed the low stability of the ester bonds towards acid hydrolysis.
- Polakova, Monika,Joniak, Dusan,Duris, Miloslav
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p. 1609 - 1618
(2007/10/03)
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- Synthesis of C-Terminal Glycopeptides from Resin-Bound Glycosyl Azides via a Modified Staudinger Reaction
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The solid-phase synthesis of glycopeptides containing the sugar at the C-terminus is reported. The method is demonstrated on a model, the endogenous antinociceptive peptide Leu-enkephalin. 2,3,4-Tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid was synthesized and immobilized onto a variety of derivatized resins. Conjugation of the first amino acid was accomplished by reaction of the resin-bound glycosyl azide with an activated amino acid, in one step, via a modified Staudinger reaction. Standard solid-phase peptide synthesis then resulted in the desired amide-linked glycopeptide. Reaction conditions and reagents for the glycosylation were varied to optimize the yield and purity of the product. The optimum conditions were found to be the use of a 4-fold molar excess of activated amino acid and 3-fold excess of tri-n-butylphosphine in tetrahydrofuran. This methodology is generally applicable to most peptide sequences and is compatible with both Boc-and Fmoc- synthetic strategies on a variety of resins.
- Malkinson, John P.,Falconer, Robert A.,Toth, Istvan
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p. 5249 - 5252
(2007/10/03)
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- ESTER LINKAGES BETWEEN LIGNIN AND GLUCURONIC ACID IN LIGNIN-CARBOHYDRATE COMPLEXES FROM FAGUS CRENATA
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Conjugate acid oxidation of benzyl esters with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and trifluoroacetic acid (TFA) was applied to the binding site analysis of ester linkages between lignin and glucuronoxylan in Fagus crenata wood.Based on the conjugate acid DDQ-oxidation of a watersoluble lignin-carbohydrate complex (LCC-WE) from the beech wood, the frequency of the ester bonds between the lignin and glucuronic acid residue of glucuronoxylan was determined to be 1.6 per molecule of LCC-WE. - Key words: Fagus crenata; Fagaceae; lignin-carbohydrate complex (LCC); 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).
- Imamura, Takeshi,Watanabe, Takashi,Kuwahara, Masaaki,Koshijima, Tetsuo
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p. 1165 - 1174
(2007/10/02)
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- SYNTHESIS, CHARACTERIZATION, AND CONFORMATION IN SOLUTION OF A NOVEL D-GLUCURONO-6,1-LACTAM DERIVATIVE
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Prolonged treatment of 2'-(sodium β-D-glucopyranosyluronate)isonicotinohydrazide with acetic anhydride in the presence of pyridine at room temperature for 110 h gave 2,3,4-tri-O-acetylgN-(diacetylamino)-β-D-glucopyranurono-1,6-lactam (2), a novel D-glucurono-6,1-lactam derivative.Its conformation in solution, examined by 1H- and 13C-n.m.r. and compared with the crystal structure, corresponds to a fairly rigid ring system, the pyranose ring adopting a near B0,3 (D) boat form in solution and a distorted 1C4 (D) chair conformation in the crystalline state.The closely related 2,3,4-tri-O-acetyl-β-D-glucopyranurono-6,1-lactone (4) and 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-glucose (3) take the distorted 1C4 (D) chair conformation, both in solution and in crystal form.Based on the crystal structure data of 4, the parameters of the Karplus-type equation, which relates vicinal-coupling constants with dihedral angles, were determined for 2,3, and 4.
- Takeda, Yasuko,Akimoto, Toshio,Kyogoku, Yoshimasa
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p. 175 - 192
(2007/10/02)
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