- Indirect Electrooxidation by Using Ruthenium Tetraoxide and Chloride Ion as Recycling Mediators. Optimization for the Oxidation of Diisopropylidene-D-glucose to the Ulose
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Various Various factors related to the yield and selectivity for the indirect electrooxidation of diidopropylidene-glucose (1) to the ulose 2 with ruthenium tetraoxide (RuO4) and chloride ion are investigated.The following is found to be optimum conditions: pH, ca. 10:solvent system, carbon tetrachloride and t-butyl alcohol (ca.9:1); current density, 10-40 mAcm2-; temperature, 20-40 deg C; catalyst amount, 2 molpercent of RuO2.2H2O (based on 1).The optimized electrolysis affords the desired 2 in 90 percent yield along with a trace of the cleavaged product 3 (0.2percent) by an overoxidation.
- Torii, Sigeru,Inokuchi, Tsutomu,Matsumoto, Shigeaki,Saeki, Takeaki,Oki, Tsunehei
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- Unprecedented 3-O-methyl-3-C-trifluoromethyl-d-ribono- (and l-lyxono)-γ-lactones synthesized by nucleophilic trifluoromethylation of d-hexose-derived cyclic ketones
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3-O-Methyl-3-C-trifluoromethyl-d-ribono-(and l-lyxono)-γ-lactones have been prepared from protected d-hexoses (gluco, galacto) by multi-step routes from d-glucose. The synthetic strategy includes the following steps: regioselective oxidation, nucleophilic trifluoromethylation with the Ruppert-Prakash reagent of 3-keto hexofuranose derivatives attacked stereoselectively from the less hindered face, protective group manipulations, and regioselective oxidation of a hemiacetalic hydroxyl. Base-catalyzed hydrolysis of two related d-ribonolactones afforded 3-O-Me-3-C-CF3-d-ribonic acid.
- Ghannay, Siwar,Brahmi, Jihed,Aouadi, Ka?ss,Msadek, Moncef,Praly, Jean-Pierre
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- Synthesis and glycosidase inhibition evaluation of (3S,4S)-3-((R)-1,2-dihydroxyethyl)pyrrolidine-3,4-diol
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A new azasugar (3S,4S)-3-((R)-1,2-dihydroxyethyl)pyrrolidine-3,4-diol (1) was obtained from commercially available D-glucose using one-pot reductive cyclization as a key step. The target product, i.e., the iminosugar isomer, was obtained in 10 steps and 24.3% overall yield. Only three column chromatography purifications were needed in this synthesis. The biological activity of the target molecule as glycosidase inhibitor was studied, but the inhibitory activity against four glycosidases was not good (IC50?>?100?μM).
- Zhang, En,Bai, Peng-Yan,Sun, Wei,Wang, Shang,Wang, Ming-Ming,Xu, Shuai-Min,Liu, Hong-Min
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- Sequential Enyne-Metathesis/Diels–Alder Strategy: Rapid Access to Sugar–Oxasteroid–Quinone Hybrids
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A sequential enyne-metathesis/Diels–Alder strategy is reported for the synthesis of a new class of sugar–oxasteroid–quinone hybrid molecules. 1,2:5,6-Di-O-isopropylidine-d-glucose was chosen as a chiral-pool starting material. Various sugar-derived enynes were synthesised from the common starting material. Dienes derived from these enynes were treated with various quinone dienophiles under Diels–Alder reaction conditions to give a library of sugar–oxasteroid–quinone hybrids.
- Sayyad, Ashik A.,Kaliappan, Krishna P.
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- Easy and stereoselective approach to α,β-unsaturated γ-lactones fused to pyranoses from furanose scaffolds
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The first facile and efficient route to pyranose-fused butenolides from furanose scaffolds, convenient for scaling up production, is described. Wittig olefination of 1,2-O-isopropylidene pentofuranos- or hexofuranos-3-uloses with a resonance-stabilized yl
- Xavier, Nuno M.,Rauter, Amelia P.
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- Synthesis and Evaluation of 2′-Deoxy-2′-Spirodiflurocyclopropyl Nucleoside Analogs
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The preparation of 2′-deoxy-2′-siprodifluorocyclopropany-lnucleoside analogs has been achieved from α-d-glucose in several steps. The key step in the synthesis was the introduction of the difluorocyclopropane through a difluorocarbene type reaction at the 2′-position. Then, a series of novel 2′-deoxy-2′-spirodifluorocyclopropanyl nucleoside analogs were synthesized using the Vorbrüggen method. All the synthesized nucleosides were characterized and subsequently evaluated against hepatitis C and influenza A virus strains in vitro.
- Liu, Xiao,Xia, Xueliang,Sun, Chenghai,Lin, Cai,Zhou, Yiqian,Hussain, Muzammal,Tang, Fei,Liu, Lu,Li, Xue,Zhang, Jiancun
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- Branched-chain functionalised carbohydrates via β-functionalised organolithium compounds
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The reaction of the epoxysugar 1 with an excess of lithium powder and a catalytic amount of DTBB (5 mol%) in THF at -78°C leads to the formation of the corresponding β-oxido functionalised organolithium intermediates 2, which by treatment with different electrophiles [H2O, D2O, Me3SiCl, PhCHO, Me2CO, (CH2)5CO] at -78°C to room temperature afford, after hydrolysis with water, the expected enantiomerically pure compounds 3. Starting from the epimeric epoxide 4 and following the same procedure, using water as electrophile, the compound 6 was isolated, the corresponding intermediate 5 having been involved in the process.
- Soler, Tatiana,Bachki, Abderrazak,Falvello, Larry R.,Foubelo, Francisco,Yus, Miguel
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- Chemoenzymatic Syntheses of Fluoro Sugar Phosphates and Analogues
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Combined chemical and enzymatic procedures are described for the preparation of fluorinated sugar phosphates and analogues.These derivatives are useful for study of sugar metabolism and for synthesis of pharmacological probes in a number of enzymatic systems utilizing sugars.
- Drueckhammer, Dale G.,Wong, Chi-Huey
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- Enantioselective preparation of 1,3-dithiane 1-oxides by asymmetric oxidation of 1,3-dithianes bearing a chiral auxiliary
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Oxidation of 1,3-dithianes bearing a chiral auxiliary derived from (+) or (-)-camphor or diacetone D-(+)-glucose by the Sharpless reagent [Ti(OPi)4-diethyl L-(+)- or D-(-)-tartrate-ButOOH] affords, with high stereoselectivity, the monosulfoxides in good to excellent yields. Removal of the chiral auxiliary by base-catalysed hydrolysis yields (R)- and (S)-1,3-dithiane 1-oxides in high yields.
- Watanabe, Yoshihiko,Ono, Yojiro,Hayashi, Shigefumi,Ueno, Yoshio,Toru, Takeshi
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- Synthesis of 3-deoxy-3-C-trifluoromethyl-D-ribose from D-xylose or D-glucose
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The synthesis of 3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-α-D-ribofuranose is described. After a first approach from a commercial D-xylose derivative which was limited by an incomplete stereoselectivity, the synthesis of the title compound was performed from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose by a reaction sequence where key steps: trifluoromethylation with CF3SiMe3 and radical deoxygenation are highly stereoselective.
- Lavaire,Plantier-Royon,Portella
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- Isolation and partial characterization of an extracellular glucansucrase from Leuconostoc mesenteroides NRRL B-1355 that synthesizes an alternating (1 goes to 6), (1 goes to 3)-alpha-D-glucan.
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Leuconostoc mesenteroides NRRL B-1355 grows on sucrose to produce two extracellular alpha-D-glucans. Although both are termed dextrans, they are chemically and physically distinct, and can be separated by fractional ethanol precipitation into fractions designated L and S. Fraction L is similar to B-512F dextran, having 95% alpha-(1 goes to 6) linkages and 5% alpha-(1 goes to 3) branch linkages, but fraction S has an alternating sequence of alpha-(1 goes to 6) and alpha-(1 goes to 3) linkages. Because of its structural differences from dextran, its different physical characteristics, and its resistance to hydrolysis by endodextranase, we have named glucan S, alternan, and the enzyme that synthesizes it from sucrose, alternansucrase. Alternansucrase has been isolated by two different methods. The first involves removal of the fraction L glucan from the culture fluid via hydrolysis by an endodextranase, followed by chromatography on Bio-Gel A5m. The void-volume fraction synthesizes only alternan, whereas the slower-migrating, second fraction synthesizes mainly dextran, together with some alternan. The second method utilized hydrophobic chromatography on O-(phenoxyacetyl) cellulose; a portion of the alternansucrase did not bind, whereas the bound portion, removed by eluting with detergent, contained both alternansucrase and dextransucrase. The glucans were identified by physical appearance, the concentration of ethanol required for precipitation, periodate-oxidation behavior, and susceptibility to hydrolysis by endodextranase. Also studied was the inhibition of the enzymes by 3-deoxy-3-fluoro-alpha-D-glucopyranosyl fluoride, tris(hydroxymethyl)aminomethane, 2-aminoethanol, and octyl beta-D-glucopyranoside.
- Cote,Robyt
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- Synthesis and analysis of a fluorinated product analogue as an inhibitor for 1-deoxy-d-xylulose 5-phosphate reductoisomerase
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1-Deoxy-d-xylulose 5-phosphate (DXP) reductoisomerase (DXR) is an NADPH-dependent enzyme catalyzing the rearrangement and reduction of DXP to methyl-d-erythritol 4-phosphate (MEP). Two mechanisms for this enzymatic reaction have been proposed, involving either an α-ketol rearrangement or a retroaldol/aldol rearrangement. In this study, a fluorinated product analogue, FCH2-MEP, was synthesized as a possible mechanism-based inactivator for DXR if the retroaldol/aldol mechanism is operative. FCH2-MEP was found to be a weak competitive inhibitor, and thus was unable to discriminate between the mechanisms. This result is due to the inability of the targeted enzyme, DXR, to oxidize FCH2-MEP to the aldehyde intermediate that is common to both mechanisms. While FCH2-MEP failed to act as a mechanism-based inactivator, the insight gained from this study will assist in the future design of inhibitors of DXR.
- Munos, Jeffrey W.,Pu, Xiaotao,Liu, Hung-wen
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- SYNTHESIS AND CRYSTAL STRUCTURE OF 3-DEOXY-3-FLUORO-1,2:5,6-DI-O-ISOPROPYLIDENE-α-D-GLUCOFURANOSE
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3-Deoxy-3-fluoro-1.2:5,6-di-O-isopropylidene-α-D-glucofuranose 4 has been synthesized and obtained crystalline.X-Ray structure analysis of the crystals has been performed.The space group was determined to be C2, a = 20.883 (12), b = 5.599 (1), c = 24.866 (13) Angstroem, β = 111.03 (3) deg.Two independent molecules are present in the asymmetric unit: on the basis of puckering parameters they show different conformations, which can be ascribed to crystal-packing requirements.
- Argentini, M.,Weinreich, R.,Oberti, Roberta,Ungaretti, Luciano
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- Modular Synthesis of Constrained Ethyl (cEt) Purine and Pyrimidine Nucleosides
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(Chemical Equation Presented). A modular and scalable approach to pyrimidine- and purine-containing constrained ethyl (cEt) nucleosides is demonstrated. Minimizing stereochemical adjustments and protecting group manipulations, diacetone glucose is convert
- Blade, Helen,Bradley, Derek,Diorazio, Louis,Evans, Timothy,Hayter, Barry R.,Howell, Gareth P.
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- Molar-scale synthesis of 1,2:5,6-Di-0-isopropylidene-α-D- allofuranose: DMSO oxidation of 1,2:5,6-Di-0-isopropylidene-α-D- glucofuranose and subsequent sodium borohydride reduction
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Two variants of oxidation with DMSO followed by sodium borohydride reduction have been investigated to make the synthesis of 1,2:5,6-di-0- isopropylidene-α-D-allofuranose (4) suitable for large-scale manufacturing.
- Christensen, Signe M.,Hansen, Henrik F.,Koch, Troels
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- Development of a Flexible and Robust Synthesis of Tetrahydrofuro[3,4- b]furan Nucleoside Analogues
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In the context of a PRMT5 inhibitor program, we describe our efforts to develop a flexible and robust strategy to access tetrahydrofuro[3,4-b]furan nucleoside analogues. Ultimately, it was found that a Wolfe type carboetherification from an alkenol derive
- Candito, David A.,Ye, Yingchun,Quiroz, Ryan V.,Reutershan, Michael H.,Witter, David,Gadamsetty, Surendra B.,Li, Hongming,Saurí, Josep,Schneider, Sebastian E.,Lam, Yu-Hong,Palte, Rachel L.
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- Synthesis method of 3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose
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The invention provides a synthesis method of 3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose. The synthesis method comprises the following steps: reacting glucose with acetone to obtain a first intermediate product; carrying out oxidation reaction on the first intermediate product through N-bromosuccinimide to obtain a second intermediate product; carrying out reduction reaction on the second intermediate product through sodium borohydride to obtain a third intermediate product; reacting benzyl chloride with the third intermediate product to obtain a fourth intermediate product; reacting the fourth intermediate product with an acidic solution to obtain a fifth intermediate product; and carrying out oxidation reaction and disproportionation reaction on the fifth intermediate product to obtain the 3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose. The 3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose is synthesized by taking the glucose with low price as a raw material through six steps.
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Paragraph 0082; 0085-0087; 0104; 0107-0109
(2021/07/01)
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- Toward the synthesis of the hypoxia selective anticancer agent BE-43547 A2
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A short and enantioselective synthesis of the 19-epi-BE-43547 A2 chiral framework has been achieved in a high yield. The challenging key C15 tertiary stereocenter was derived from d-glucose. The synthetic strategy involves a Julia-Kocienski olefination to install the lipophilic side chain. An efficient protocol for Z to E isomerization of olefin was developed using a novel UV flow reactor. In addition, an unprecedented oxygen mediated hydroboration and the Krapcho decarboxylation of β-keto lactone were observed. This journal is
- Kranthikumar, Ramagonolla
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supporting information
p. 9833 - 9839
(2021/12/07)
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- PRMT5 INHIBITORS
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The present invention provides a compound of Formula (I) and the pharmaceutically acceptable salts, esters, and prodrugs thereof, which are PRMT5 inhibitors. Also provided are methods of making compounds of Formula I, pharmaceutical compositions comprising compounds of Formula I, and methods of using these compounds to treat cancer, sickle cell, and hereditary persistence of foetal hemoglobin (HPFH) mutations.
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Page/Page column 90
(2020/03/02)
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- Synthesis and Structure-Activity Relationship Studies of C2-Modified Analogs of the Antimycobacterial Natural Product Pyridomycin
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A series of derivatives of the antimycobacterial natural product pyridomycin have been prepared with the C2 side chain attached to the macrocyclic core structure by a C-C single bond, in place of the synthetically more demanding enol ester double bond found in the natural product. Hydrophobic C2 substituents of sufficient size generally provide for potent anti-Mtb activity of these dihydropyridomycins (minimum inhibitory concentration (MIC) values around 2.5 μM), with several analogs thus approaching the activity of natural pyridomycin. Surprisingly, some of these compounds, in contrast to pyridomycin, are insensitive to overexpression of InhA in Mycobacterium tuberculosis (Mtb). This indicates that their anti-Mtb activity does not critically depend on the inhibition of InhA and that their overall mode of action may differ from that of the original natural product lead.
- Kienle, Maryline,Eisenring, Patrick,Stoessel, Barbara,Horlacher, Oliver P.,Hasler, Samuel,Van Colen, Gwéna?lle,Hartkoorn, Ruben C.,Vocat, Anthony,Cole, Stewart T.,Altmann, Karl-Heinz
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supporting information
p. 1105 - 1131
(2020/03/10)
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- Synthesis and antiviral activity of some imidazo[1,2-b][1,3,4]thiadiazole carbohydrate derivatives
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Herein we describe the synthesis of imidazo[2,1-b][1,3,4]thiadiazoles from carbohydrates with D-ribo and D-xylo configuration. The antiviral activity of these compounds was tested against Junín virus (the etiological agent of Argentine hemorrhagic fever). The p-chlorophenyl derivatives showed antiviral activity in a range of micromolar concentration.
- Fascio, Mirta L.,Sepúlveda, Claudia S.,Damonte, Elsa B.,D'Accorso, Norma B.
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- METHOD FOR PRODUCING NUCLEOSIDE DERIVATIVE
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PROBLEM TO BE SOLVED: To provide a practical method for producing a nucleoside derivative that is applied to RNA pharmaceuticals or the like. SOLUTION: The present invention provides a method for producing a nucleotide derivative represented by a compound
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Paragraph 0157
(2020/05/13)
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- Microwave-assisted Synthesis of Hybrid Heterocyclics as Biological Potent Molecules
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A series of novel 5-((1H-benzo[d]imidazol-2-yl)methyl)-2-((3aR,5S,6S,6aR)-2,2-dimethyl-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-3-phenylthiazolidin-4-ones 9a–n has been synthesized from triazole-linked thiazolidinone derivatives 8a–g with o-phenylenediamine and characterized by IR, NMR, MS, and elemental analyses. Further, these compounds were screened for their antibacterial activity against Gram-positive bacteria, namely, Bacillus subtilis (ATCC 6633), Staphylococcus aureus (ATCC 6538p), and Micrococcus luteus (IFC 12708), and Gram-negative bacteria, namely, Proteus vulgaris (ATCC 3851), Salmonella typhimurium (ATCC 14028), and Escherichia coli (ATCC 25922). Among the screened compounds, compounds 9b, 9d, 9h, and 9i are highly active against almost all selected bacterial strains; the remaining compounds showed moderate to good activity and emerged as potential molecules for further development.
- Srinivas,Sunitha,Vasumathi Reddy,Karthik,Rajesh Kumar
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p. 1564 - 1573
(2018/05/30)
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- COMPOUNDS FOR THE TREATMENT OF SYSTEMIC INSULIN RESISTANCE DISORDERS AND THE USE THEREOF
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Aspects of the invention relate to novel synthetic compounds for treatment of metabolic diseases partially associated with systemic insulin resistance caused by Galectin proteins binding and inhibiting insulin and TGFb1 receptors causing physiological disturbances in the insulin pathways.
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Paragraph 00260-00262
(2018/12/03)
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- The direct and highly diastereoselective synthesis of 3,4-epoxy-2-piperidones. Application to the total synthesis and absolute configurational assignment of 3α,4α-epoxy-5β-pipermethystine
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The substrate-controlled asymmetric total synthesis and absolute configurational assignment of biologically active 3α,4α-epoxy-5β-pipermethystine, a minor component in the aerial parts of kava, has been achieved by featuring, as a key step, the environmentally friendly and direct synthesis of 2,3-epoxyamides from allyl amines. By using the chiron approach, first a carbohydrate-derived dehydropiperidine was prepared and subjected to a stereoselective tandem C-H/CC oxidation reaction. In this attempt, the required α,α-trans-epoxy-2-piperidone skeleton of the kava metabolite precursor was not achieved, although the tandem oxidation was highly stereoselective. However, starting from non-carbohydrate 3-hydroxy-4,5-dehydropiperidine, and using the same tandem oxidation, the target intermediate was obtained in high yield and complete unprecedented anti-stereoselectivity. Since the proposed mechanistic course of this tandem oxidation implies the transient formation of an α,β-unsaturated amide followed by the subsequent epoxidation reaction, this second approach supports the previously established biotransformation proposal of (-)-pipermethystine to (-)-3α,4α-epoxy-5β-pipermethystine.
- Osorio-Nieto, Urbano,Vázquez-Amaya, Laura Y.,H?pfl, Herbert,Quintero, Leticia,Sartillo-Piscil, Fernando
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- Total syntheses of Prelactone V and Prelactone B
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The total syntheses of natural products Prelactone-V and Prelactone-B have been accomplished by a novel Chiron approach starting from D-glucose. The synthesis involves isopropylidene acetal formation of D-glucose using Poly(4-vinylpyridine) supported iodine as a catalyst, Tebbe olefination, Grignard reaction, Wittig olefination, selective mono deprotection of acetal using PMA/SiO2, hydrogenation and anti-1,3-diol formation are as key steps.
- Raghavendra,Tadiparthi, Krishnaji,Yadav
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supporting information
p. 17 - 19
(2017/03/15)
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- Synthesis and In Vitro Study of Hybrid Heterocyclic's as Potential Nematicidal Agents
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A series of novel 5-((3aR,5S,6S,6aR)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-3-(4-fluorophenyl)-6-phenyl-3,3a,5,6-tetrahydroisoxazolo[3,4-d]thiazoles 10a–g were synthesized by the reaction of chalcone derivatives of 2-((3aR,5S,6S,6aR)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-3-phenylthiazolidin-4-one 9 with hydroxylamine hydrochloride. The chemical structures of newly synthesized compounds were elucidated by IR, NMR, MS, and elemental analysis. The compounds 10 a–g were evaluated for their nematicidal activity against Dietylenchus myceliophagus and Caenorhabditis elegans; compound 10e and 10f showed appreciable nematicidal activity. Further, the compounds 10a – g were screened for their antifungal activity against Candida albicans (ATCC 10231), Aspergillus fumigates (HIC 6094), Trichophyton rubrum (IFO 9185), and Trichopyton mentagrophytes (IFO 40996). The compounds 10b and 10f displayed notable antifungal activity against all the microorganisms employed. The activity of these compounds is almost equal to the standard. It is also interesting to note that the compounds 10b and 10f and 10g showed activity towards C. albicans at the concentration of 3.75?μM, which is less than the concentration of the standard Amphotericin B.
- Srinivas,Sunitha,Karthik,Nikitha,Raju,Ravinder,Anusha,Rajasri,Swapna,Swaroopa,Srinivas,Vasumathi Reddy
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p. 3250 - 3257
(2017/10/05)
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- Synthesis, nematicidal and antifungal properties of hybrid heterocyclics
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A new series of 5-((3aR, 5S, 6S, 6aR)-6-((1-(4-chlorophenyl)-1H-1, 2, 3-triazol-4-yl)methoxy)-2, 2-dimethyltetrahydrofuro[ 2, 3-d][1, 3]dioxol-5-yl)-3-(4-fluorophenyl)-2, 6-diphenyl-3, 3a, 5, 6-tetrahydro-2H-pyrazolo[3, 4-d]thiazoles 10a-r was synthesized by the reaction of chalcone derivatives of 2-((3aR, 5S, 6S, 6aR)-6-((1-(4-chlorophenyl)-1H-1, 2, 3-triazol-4-yl)methoxy)-2, 2-dimethyltetrahydrofuro[2, 3-d][1, 3]dioxol-5-yl)-3-phenylthiazolidin-4-one 9 with aryl/alkyl hydrazines. The chemical structures of newly synthesized compounds were elucidated by IR, NMR, MS and elemental analysis. The compounds 10a-r were evaluated for their nematicidal activity against Dietylenchus myceliophagus and Caenorhabditis elegans by aqueous in vitro screening technique. Among them, compounds containing N-benzylpyrazole moiety (10d, 10j, 10p), and N-methylpyrazole moiety (10f, 10i, 10r) showed significant nematicidal activity against both tested nematodes with LD50 160-210 ppm, almost equal to oxamyl standard. Further, these compounds 10a-r were screened for their antifungal (MZI, MIC, and MFC) activity against four fungal organisms viz, Candida albicans (ATCC 102331), Aspergillus fumigates (HIC 6094), Trichophyton rubrum (IFO 9185) and Trichophyton mentagrophytes (IFO 40996). Most of the new compounds showed appreciable activity against the tested fungi, and emerged as potential molecules for further development.
- Srinivas, Avula,Sunitha, Malladi,Karthik, Pulluri,Reddy, K. Vasumathi
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p. 1030 - 1041
(2018/01/17)
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- Larger laboratory scale synthesis of 5-methyluridine and formal synthesis of its L-enantiomer
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A larger laboratory scale synthesis (>60 g per run) of 5-methyluridine is presented. The critical intermediate 1,2-O-isopropylidene-α-D-ribofuranose was prepared from very cheap D-glucose via D-allose. Its L-enantiomer was obtained from L-arabinose via L-glucose, and also from L-xylose. {figure presented}.
- Thiesen, Luciano J. Hoeltgebaum,Cabral, Nadia,Joselice E Silva, Maria,Bezerra, Gilson,Doboszewski, Bogdan
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p. 249 - 264
(2017/06/19)
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- Reversal of Stereoselectivity in Cycloadditions of Five-Membered Cyclic Nitrones Derived from Hexoses
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Two five-membered cyclic nitrones derived from hexoses, a newly synthesized d-allo-configured nitrone and an already known d-talo-configured nitrone, have been examined in 1,3-dipolar cycloaddition reactions with vinyl acetate, allyl benzoate, methyl acrylate, acrylonitrile, and vinylene carbonate. The reactions of the d-allo-configured nitrone proceeded preferentially through the expected exo-anti transition state, but all the cycloadditions of the d-talo-configured nitrone surprisingly showed high exo-syn selectivity. This reversal of stereoselectivity has been explained by 3D analysis of the preferred conformations of the nitrones, obtained from X-ray data. The structures were further inspected using CONFLEX, PM5, and DFT calculations. All these methods revealed that the dioxolane substituents attached to C-5 of both nitrones had opposite spatial locations.
- Malatinsky, Tomá?,Spi?áková, Mária,Babjak, Matej,Doháňo?ová, Jana,Marek, Jaromír,Moncol, Ján,Fischer, Róbert
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p. 1086 - 1098
(2017/02/23)
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- Organocatalyzed asymmetric Michael addition by an efficient bifunctional carbohydrate-thiourea hybrid with mechanistic DFT analysis
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A series of thiourea based bifunctional organocatalysts having d-glucose as a core scaffold were synthesized and examined as catalysts for the asymmetric Michael addition reaction of aryl/alkyl trans-β-nitrostyrenes over cyclohexanone and other Michael donors having active methylene. Excellent enantioselectivities (0. The obtained results were explained through DFT calculations using the B3LYP/6-311G(d,p)//B3LYP/6-31G(d) basic set. The QM/MM calculations revealed the role of cyclohexanone as a solvent as well as reactant in the rate determining step imparting 31.91 kcal mol?1 of energy towards the product formation.
- Azad, Chandra S.,Khan, Imran A.,Narula, Anudeep K.
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supporting information
p. 11454 - 11461
(2016/12/18)
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- METHOD FOR PRODUCING AVENACIOLIDES AND USES THEREOF
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Disclosed herein are novel uses of avenaciolide derivatives and the preparation method of producing the same. The avenaciolide derivatives may suppress or inhibit the growth of gram-positive bacteria, including the notorious methicillin-resistant Staphylococcus aureus. Accordingly, the avenaciolides derivatives are potential lead compounds for the development of next generation antibiotics for the treatment of disease and/or disorders related to infection caused by gram-positive bacteria.
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Paragraph 0141; 0142; 0143; 0144
(2016/10/31)
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- Oligomeric compounds having at least one neutrally linked terminal bicyclic nucleoside
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The present disclosure describes oligomeric compounds having at least one bicyclic nucleoside attached to the 3′ or 5′ termini by a neutral internucleoside linkage and methods of using the oligomeric compounds. In some embodiments, the oligomeric compounds provided herein hybridize to a portion of a target RNA resulting in loss of normal function of the target RNA.
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Page/Page column 39; 41
(2016/04/20)
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- Synthesis and biological evaluation of triazole linked thiazolidenone glycosides
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In a one pot procedure a series of novel triazole linked thiazolidinone derivatives 8a-g and 9a-g was prepared by condensation of (3aR,5S,6R,6aR)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydro[2,3-d] [1,3]dioxole-5-carbaldehyde 7 with mercapto acids and primary amines in the presence of ZnCl2 under both microwave irradiation and conventional heating conditions. Compound 7 was prepared from diacetone D-glucose with oxidation followed by reduction, click reaction, primary acetonide deprotection and with oxidative cleavage. Characterization of new compounds has been done by means of IR, NMR, MS and elemental analysis. The nematicidal and antibacterial activity of the compounds has also been evaluated.
- Srinivas, Avula,Santhosh, Madavarapu,Sunitha, Malladi,Karthik, Pulluri,Srinivas, Kontham,Reddy, K.Vasumathi
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p. 827 - 836
(2016/12/18)
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- Titanocene dihalides and ferrocenes bearing a pendant α-d- xylofuranos-5-yl or α-d-ribofuranos-5-yl moiety. synthesis, characterization, and cytotoxic activity
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Titanocene dichlorides of general formula [(η5-C 5H5)(η5-C5H4R) TiCl2] (where R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-α- d-xylofuranos-5-yl (Xylf) (8a); R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl- α-d-ribofuranos-5-yl (Ribf) (8b)) and [(η5-C 5H4R)2TiCl2] (R = Xylf (9a); R = Ribf (9b)) were prepared by reaction of the corresponding lithium cyclopentadienides 7a,b with an equimolar amount of [(η5-C 5H5)TiCl3] or a 0.5 mol amount of [TiCl 4(THF)2]. Titanocene difluorides of the general formula [(η5-C5H4R1)(η5- C5H4R2)TiF2] (R1 = H and R2 = Ribf (10); R1 = R2 = Xylf (11a); R 1 = R2 = Ribf (11b)) were obtained by fluorination of the corresponding titanocene dichlorides 8b and 9 with the fluorinating agent {2-(CH2NMe2)C6H4-κC,N}(n-Bu) 2SnF in high yields. Alternatively, complexes 11 were prepared in a straightforward way by direct reaction of [TiF4(THF)2] with 2 equiv of the corresponding lithium cyclopentadienide 7a,b. Ferrocene complexes [(η5-C5H4R)2Fe] (R = Xylf (12a); R = Ribf (12b)) were synthesized by metathesis of 2 equiv of lithium cyclopentadienide 7a,b and 1 equiv of anhydrous FeCl2. Deprotection of the benzyl group in ferrocenes 12 proceeded cleanly by a catalytic hydrogenation on Pd/C and afforded the ferrocene diols [(η5- C5H4R)2Fe] (R = 5-deoxy-1,2-di-O- isopropylidene-α-d-xylofuranos-5-yl (Xylf-OH) (14a); R = 5-deoxy-1,2-di-O-isopropylidene-α-d-ribofuranos-5-yl (Ribf-OH) (14b)). A scaled up benzyl deprotection with Et3SiH as a hydrogen source led to the replacement of only one benzyl group, which gave the ferrocene alcohol [(η5-C5H4R1)(η5- C5H4R2)Fe] (R1 = Xylf and R 2 = Xylf-OH (13)). The prepared complexes were characterized by elemental analysis, melting point determination, NMR, IR, and ESI-MS, and the molecular structure of 9b was determined by X-ray diffraction analysis. The cytotoxic activity of complexes 8-14 against A2780 and A2780cis cancer cells was evaluated by MTT tests. Titanocene difluorides 10 and 11 and ferrocene diol 14a showed cytotoxicity against A2780 cells in the medium to low micromolar range, while the most active species, 11b, displayed about 40% higher cytotoxicity against A2780cis in comparison to a cisplatin standard.
- Hodik, Tomas,Lamac, Martin,Cervenkova St'Astna, Lucie,Karban, Jindrich,Koubkova, Lucie,Hrstka, Roman,Cisarova, Ivana,Pinkas, Jiri
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p. 2059 - 2070
(2014/05/20)
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- Glucose positions affect the phloem mobility of glucose-fipronil conjugates
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In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.
- Lei, Zhiwei,Wang, Jie,Mao, Genlin,Wen, Yingjie,Tian, Yuxin,Wu, Huawei,Li, Yufeng,Xu, Hanhong
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p. 6065 - 6071
(2015/04/22)
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- An approach to the carbon backbone of bielschowskysin, part 1: Photocyclization strategy
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Several macrocyclization reaction attempts of highly advanced precursors toward a total synthesis of marine diterpene bielschowskysin are disclosed. Biomimetic [2+2]-photocyclization reactions were applied to construct the cyclobutane core in these intermediates, which could be accessed along scalable high-yielding reaction sequences from cheap enantiopure starting-materials. Asymmetric syntheses of various highly functionalized intermediates toward the total synthesis of bielschowskysin (1) are described. In particular a biomimetic [2+2]-photocycloaddition reaction strategy, forming the cyclobutane core, was followed by various macrocyclization reactions attempts. Copyright
- Himmelbauer, Martin,Farcet, Jean-Baptiste,Gagnepain, Julien,Mulzer, Johann
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p. 8214 - 8244
(2014/01/06)
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- Sugar furanoid trans-vicinal diacid as a γ-turn inducer: Synthesis and conformational study
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A simple method for the synthesis of a sugar furanoid trans vicinal diacid and its incorporation into the N-terminal tetrapeptide sequence (H-Phe-Trp-Lys-Thr-OH) to get glycopeptide 8 has been described. 2D NMR and MD simulation studies of 8 clearly show that the sugar diacid adopts a γ-turn conformation towards the N-terminus.
- Vangala, Madhuri,Dhokale, Snehal A.,Gawade, Rupesh L.,Pattuparambil, Rajamohanan R.,Puranik, Vedavati G.,Dhavale, Dilip D.
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p. 6874 - 6878
(2013/10/08)
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- A practical access to glucose- and allose-based (5+5) 3- spiropseudonucleosides from a common intermediate
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A practical access to glucose-based and allose-based spirooxazolidinones is reported. The synthetic sequence consisting of TEMPO-catalyzed oxidation of 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose, Henry reaction, and reduction provides amino alcohol with allo-configuration on a multigram scale. Alternatively, water elimination from Henry products followed by a rehydration gives an access to diastereomerically pure glucose-based nitro alcohol which upon reduction provides complementary amino alcohol with gluco-configuration. The latter amino alcohols are transformed into spirooxazolidinones (3-spiropseudonucleosides) via their N-Cbz or N-phenylcarbamate derivatives. The title compounds easily undergo N-derivatization and give highly crystalline materials. Two of the newly obtained (5+5) 3-spiropseudonucleosides are characterized by X-ray crystallography.
- Turks, Maris,Rodins, Vitalijs,Rolava, Evija,Ostrovskis, Pavels,Belyakov, Sergey
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supporting information
p. 5 - 15
(2013/07/27)
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- N-Thiocarbonyl iminosugars: Synthesis and evaluation of castanospermine analogues bearing oxazole-2(3H)-thione moieties
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A straightforward and efficient synthetic route to a new class of glycosidase inhibitors containing an oxazole-2(3H)-thione moiety has been devised. The approach involves the formation of α-hydroxy ketones, which, after condensation with thiocyanic acid, leads to the formation of the heterocycle. By exploiting the ability of the nitrogen atom of oxazoline-2-thione precursors to act as nucleophiles in intramolecular addition, castanospermine analogues could be readily prepared in good overall yields. Glycosidase inhibitory activity compared to oxazolidinethione analogues showed a strong influence of the double bond, for example with pseudoiminosugar 19, by suppressing α-glucosidase inhibition and introducing, to a moderate level, β-glucosidase inhibitory activity. Reactivities showed the propensity of oxazole-2(3H)-thiones - especially when fused on carbohydrate frames - to convert into 1,3-oxazolidine-2-thione aminals through nucleophilic addition to the double bond, leading to unexpected tricyclic structure 21. Oxazole-2(3H)-thione moieties have been anchored onto carbohydrates in a five-step sequence that allows access to castanospermine analogues. Copyright
- Silva, Sandrina,Sanchez-Fernandez, Elena M.,Ortiz Mellet, Carmen,Tatibouet, Arnaud,Pilar Rauter, Amelia,Rollin, Patrick
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p. 7941 - 7951
(2014/01/06)
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- Pyridinium o-iodoxybenzoate as a safe form of a famous oxidant
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The stable pyridinium salt of o-iodoxybenzoic acid (PIBX) that is easy to obtain can serve as a convenient substitute of IBX as an oxidant. PIBX is safer, has neutral properties behaves as an equivalent to IBX in the oxidation of alcohols to ketones or aldehydes in polar solvents (DMF, DMSO), and provides higher oxidation rate in THF due to better solubility.
- Kumanyaev, Ivan M.,Lapitskaya, Margarita A.,Vasiljeva, Ljudmila L.,Pivnitsky, Kasimir K.
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experimental part
p. 129 - 131
(2012/09/05)
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- Sugar-amino acid cyclic conjugates as novel conformationally constrained hydroxyethylamine transition-state isosteres
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Hydroxyethylamine (HEA) isosteres have previously been shown to display a multitude of biomedical applications. In fact, the first protease inhibitor, saquinavir is an HEA based peptidomimetic. Herein we describe an easy-to-operate synthetic route to a series of carbohydrate-based conformationally constrained hydroxyethylamine (HEA) isosteres featuring amino acid side chains, starting from d-glucose. This class of novel sugar-amino acid-tethered conformationally restricted HEA systems may have bearing in practical application, particularly in the development of conformationally restricted protease inhibitors.
- Roy, Arup,Sanjayan, Gangadhar J.
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supporting information; scheme or table
p. 3361 - 3363
(2012/07/28)
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- Azetidine iminosugars from the cyclization of 3,5-Di- O -triflates of α-furanosides and of 2,4-Di- O -triflates of β-pyranosides derived from glucose
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Primary amines with either 3,5-di-O-ditriflates of α-furanosides or 2,4-di-O-triflates of β-pyranosides form bicyclic azetidines in high yield.
- Lenagh-Snow, Gabriel M. J.,Araujo, Noelia,Jenkinson, Sarah F.,Martinez, R. Fernando,Shimada, Yousuke,Yu, Chu-Yi,Kato, Atsushi,Fleet, George W.J.
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supporting information; experimental part
p. 2142 - 2145
(2012/07/13)
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- Synthesis of novel 3-deoxy-3-C-triazolylmethylallose derivatives and evaluation of their biological activity
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Recently, monosaccharide-triazole conjugates have proved to possess a large variety of useful biological activities. This paper describes synthesis of a new series of 3-deoxy-3-C-triazolylmethyl-allose derivatives. These new compounds are obtained from ac
- Rjabova, Jekaterina,Rjabovs, Vitalijs,Vargas, Antonio J. Moreno,Clavijo, Elena Moreno,Turks, Maris
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scheme or table
p. 386 - 394
(2012/09/08)
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- Intramolecular base-free sonogashira reaction for the synthesis of benzannulated chiral macrocycles embedded in carbohydrate templates
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A base-free, intramolecular Sonogashira reaction-based general approach has been established for the diversity-oriented synthesis (DOS) of fused bi- and tricyclic systems containing benzannulated, 10- to 13-membered chiral macrocycles embedded in carbohydrate templates. Macrocycles with different ring sizes have been prepared by pre-designing the chiral building blocks. Base-sensitive groups like acetyl and TBDPS survived the reaction conditions. Copyright
- Hussain, Altaf,Yousuf, Syed Khalid,Kumar, Deepak,Lambu, Malikharjunarao,Singh, Baldev,Maity, Sudip,Mukherjee, Debaraj
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scheme or table
p. 1933 - 1940
(2012/09/22)
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- Design of β-amino acid with backbone-side chain interactions: Stabilization of 14/15-helix in α/β-peptides
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A new C-linked carbo-β-amino acid, (R)-β-Caa(r), having a carbohydrate side chain with d-ribo configuration, was prepared from d-glucose by inverting the C-3 stereocenter to introduce constraints/ interactions. From the NMR studies it was inferred that the new monomer may participate in additional electrostatic interactions, facilitating and enhancing novel folds in oligomeric peptides derived from it. The α/β- peptides, synthesized from alternating l-Ala and (R)-β-Caa(r), have shown the presence of 14/15-helix by NMR (in CDCl3, methanol-d3 and CD3CN), CD and MD calculations. The hybrid peptides showed the presence of electrostatic interactions involving the intraresidue amide proton and the C3-OMe, which helped in the stabilization of the NH(i)???CO(i-4) H-bonds and adoption of 14/15-helix. The importance of such additional interactions has been well defined in recent times to stabilize the folding in a variety of peptidic foldamers. These observations suggest and emphasize that the side chain-backbone interactions are crucial in the stabilization of the desired folding propensity. The designed monomer thus enlarges the opportunities for the synthesis of peptides with novel conformations and expands the repertoire of the foldamers.
- Sharma, Gangavaram V. M.,Yadav, Thota Anupama,Choudhary, Madavi,Kunwar, Ajit C.
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scheme or table
p. 6834 - 6848
(2012/10/07)
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- A carbohydrate approach for the formal total synthesis of the prostacyclin analogue (16S)-iloprost
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The formal total synthesis of the synthetic and stable analogue of prostacyclin, (16S)- iloprost is described via a convergent synthesis starting from readily available d-glucose. Julia olefination and the aldol reaction are the key steps involved in the synthesis.
- Chandrasekhar, Srivari,Sridhar, Chirumarry,Srihari, Pabbaraja
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experimental part
p. 388 - 394
(2012/07/14)
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- Synthesis of 1,2,3-triazole glycoconjugates as inhibitors of α-glucosidases
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Ten new 1,2,3-triazole glycoconjugates were synthesized from d-glucose and evaluated in in vitro assays for their ability to inhibit the enzyme α-glucosidase. Most of the compounds had low activity or were inactive when compared with acarbose. However, the derivative 1,2-O-isopropylidene-3- phenyl-5-(4-phenyl-1H-1,2,3-triazole-1-yl)-α-d-ribofuranose (19i) possessed activity comparable with the standard drug. The influence of the phenyl group on carbon 3 of the carbohydrate framework is discussed.
- Da Rocha, David R.,Santos, Wilson C.,Lima, Emerson S.,Ferreira, Vitor F.
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experimental part
p. 14 - 19
(2012/03/26)
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- Molecular recognition at the active site of catechol-O-methyltransferase (COMT): Adenine replacements in bisubstrate inhibitors
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L-Dopa, the standard therapeutic for Parkinson's disease, is inactivated by the enzyme catechol-O-methyltransferase (COMT). COMT catalyzes the transfer of an activated methyl group from S-adenosylmethionine (SAM) to its catechol substrates, such as L-dopa, in the presence of magnesium ions. The molecular recognition properties of the SAM-binding site of COMT have been investigated only sparsely. Here, we explore this site by structural alterations of the adenine moiety of bisubstrate inhibitors. The molecular recognition of adenine is of special interest due to the great abundance and importance of this nucleobase in biological systems. Novel bisubstrate inhibitors with adenine replacements were developed by structure-based design and synthesized using a nucleosidation protocol introduced by Vorbrueggen and co-workers. Key interactions of the adenine moiety with COMT were measured with a radiochemical assay. Several bisubstrate inhibitors, most notably the adenine replacements thiopyridine, purine, N-methyladenine, and 6-methylpurine, displayed nanomolar IC50 values (median inhibitory concentration) for COMT down to 6 nM. A series of six cocrystal structures of the bisubstrate inhibitors in ternary complexes with COMT and Mg2+ confirm our predicted binding mode of the adenine replacements. The cocrystal structure of an inhibitor bearing no nucleobase can be regarded as an intermediate along the reaction coordinate of bisubstrate inhibitor binding to COMT. Our studies show that solvation varies with the type of adenine replacement, whereas among the adenine derivatives, the nitrogen atom at position 1 is essential for high affinity, while the exocyclic amino group is most efficiently substituted by a methyl group. Copyright
- Ellermann, Manuel,Paulini, Ralph,Jakob-Roetne, Roland,Lerner, Christian,Borroni, Edilio,Roth, Doris,Ehler, Andreas,Schweizer, W. Bernd,Schlatter, Daniel,Rudolph, Markus G.,Diederich, Francois
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supporting information; experimental part
p. 6369 - 6381
(2011/08/06)
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- Sugar-monophosphite ligands applied to the asymmetric Ni-catalyzed trialkylaluminum addition to aldehydes
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A series of readily available sugar-based phosphite ligands were applied to the Ni-catalyzed asymmetric trialkylaluminum additions to aldehydes. The ability of the catalysts to transfer chiral information to the product could be tuned by choosing suitable ligand components (configuration at C-3 of the furanoside backbone; the steric hindrance of the substituent at C-3 and the substituents/configuration of the biaryl phosphite moieties). Good enantioselectivities (ee's up to 84%) were obtained for several aryl aldehydes using several organoaluminum sources.
- Alegre, Sabina,Dieguez, Montserrat,Pmies, Oscar
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scheme or table
p. 834 - 839
(2011/08/22)
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- Synthesis and biophysical evaluation of 3′-Me-α-l-LNA - Substitution in the minor groove of α-l-LNA duplexes
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The synthesis and biophysical evaluation of 3′-Me-α-l-LNA is reported. The synthesis of the nucleoside building block phosphoramidite was accomplished starting from diacetone glucose. The 3′-Me group was introduced in the desired configuration by hydride
- Seth, Punit P.,Allerson, Charles A.,stergaard, Michael E.,Swayze, Eric E.
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scheme or table
p. 4690 - 4694
(2011/09/20)
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- Synthesis and biological evaluation of 2′,4′- and 3′,4′-bridged nucleoside analogues
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Most nucleosides in solution typically exist in equilibrium between two major sugar pucker forms, N-type and S-type, but bridged nucleosides can be locked into one of these conformations depending on their specific structure. While many groups have researched these bridged nucleosides for the purpose of determining their binding affinity for antisense applications, we opted to look into the potential for biological activity within these conformationally-locked structures. A small library of 2′,4′- and 3′,4′-bridged nucleoside analogues was synthesized, including a novel 3′,4′- carbocyclic bridged system. The synthesized compounds were tested for antibacterial, antitumor, and antiviral activities, leading to the identification of nucleosides possessing such biological activities. To the best of our knowledge, these biologically active compounds represent the first example of 2′,4′-bridged nucleosides to demonstrate such properties. The most potent compound, nucleoside 33, exhibited significant antiviral activity against pseudoviruses SF162 (IC50 = 7.0 μM) and HxB2 (IC50 = 2.4 μM). These findings render bridged nucleosides as credible leads for drug discovery in the anti-HIV area of research.
- Nicolaou,Ellery, Shelby P.,Rivas, Fatima,Saye, Karen,Rogers, Eric,Workinger, Tyler J.,Schallenberger, Mark,Tawatao, Rommel,Montero, Ana,Hessell, Ann,Romesberg, Floyd,Carson, Dennis,Burton, Dennis
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body text
p. 5648 - 5669
(2011/10/31)
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- Inhibition of nonmammalian glycosidases by azetidine iminosugars derived from stable 3,5-Di-O-triflates of pentoses
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Efficient ring closure of stable crystalline 3,5-di-O-triflates of pentofuranosides with amines to form azetidines allowed preliminary evaluation of four-ring iminosugars as glycosidase inhibitors; significant and specific inhibition of nonmammalian α-glucosidases is shown by l-xylo- and l-arabino-iminosugar azetidines.
- Lenagh-Snow, Gabriel M. J.,Araujo, Noelia,Jenkinson, Sarah F.,Rutherford, Catherine,Nakagawa, Shinpei,Kato, Atsushi,Yu, Chu-Yi,Weymouth-Wilson, Alexander C.,Fleet, George W. J.
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supporting information; experimental part
p. 5834 - 5837
(2012/01/06)
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- Synthesis of mycinose from 1,2:5,6-Di-O-isopropylidene-α-D- glucofuranose
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A facile synthesis of mycinose from commercially available 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose was developed. A selective and direct reductive debromination of α-hydroxy bromides in a simple NaBH4/EtOH/H2O system was found.
- Bao, Kai,Gao, Hao,Zhu, Zhibin,Wang, Jinhong,Zhang, Guoning,Sun, Jun,Zhang, Weige,Yao, Xinsheng
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scheme or table
p. 592 - 595
(2012/05/31)
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- Synthesis of a MUC1-glycopeptide-BSA conjugate vaccine bearing the 3′-deoxy-3′-fluoro-Thomsen-Friedenreich antigen
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A novel MUC1-glycopeptide-BSA conjugate vaccine with a specifically fluorinated Thomsen-Friedenreich antigen side chain at Thr6 was prepared. Preliminary immunological experiments reveal specific binding of the tumor-associated glycopeptide antigen analog by anti-MUC1-mouse antibodies.
- Hoffmann-Roeder, Anja,Johannes, Manuel
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supporting information; experimental part
p. 9903 - 9905
(2011/10/09)
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- Synthesis, Biological Activity, and Molecular Modeling Studies of 1H-1,2,3-Triazole Derivatives of Carbohydrates as a-Glucosidases Inhibitors
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A class of drugs in use for treating type II diabetes mellitus (T2D), typified by the pseudotetrasaccharide acarbose, act by inhibiting the a-glucosidase activity present in pancreatic secretions and in the brush border of the small intestine. Herein, we report the synthesis of a series of 4-substituted 1,2,3-triazoles conjugated with sugars, including D-xylose, D-galactose, D-allose, and D-ribose. Compounds were screened for a-glucosidase inhibitory activity using yeast maltase (MAL12) as a model enzyme. Methyl2,3-O-isopropylidene-β-D-ribofuranosides, such as the 4-(l-cyclohexenyl)-l,2,3-triazole derivative, were among the most active compounds, showing up to 25-fold higher inhibitory potency than the complex oligosaccharide acarbose. Docking studies on a MAL12 homology model disclosed a binding mode consistent with a transition-state-mimicking mechanism. Finally, the actual pharmacological potential of this triazole series was demonstrated by the reduction of postprandial blood glucose levels in normal rats. These compounds could represent new chemical scaffolds for developing novel drugs against T2D.
- Ferreira, Sabrinab,Sodero, Ana C. R.,Cardoso, Mariana F. C.,Lima, Emerson S.,Kaiser, Carlos R.,Silva Jr., Floriano P.,Ferreira, Vitor F.
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supporting information; experimental part
p. 2364 - 2375
(2010/09/04)
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- Synthesis and antibacterial activity of aminodeoxyglucose derivatives against Listeria innocua and Salmonella typhimurium
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In this study aminodeoxyglucose derivatives were synthesized and evaluated for their antibacterial activity against two food bacteria, Listeria innocua and Salmonella typhimurium. 6-Amino-6-deoxy-α-Dmethylglucopyranose (GSA-6), 3-amino-3-deoxy-D-glucopyranoside (GSA-3), and β-D-glucopyranosylamine (GSA-1) were synthesized and concurrently tested with commercially available D-glucosamine (GSA-2) for antibacterial activity. Results obtained from this study showed a pronounced antagonist effect due to the position of amino groups of aminoglucose derivatives on the antibacterial activity. GSA-3 was the most active compound. At a concentration of 2 × 10 -4 mol mL -1, it delayed the growth of both bacteria with percentages of inhibition of 29 and 15% for L. innocua and S. typhimurium, respectively. At the same concentration the percentages of inhibition for other aminodeoxyglucoses varied between 5 and 18% and between 2 and 11% for L. innocua and S. typhimurium, respectively. All compounds were characterized by FTIR, 1H NMR, and 13C NMR spectroscopy.
- Theoneste, Muhizi,Stephane, Greller,Veronique, Coma
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experimental part
p. 8770 - 8775
(2010/07/17)
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- Synthesis and evaluation of 3″- and 4″-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000
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Four 3″- and 4″-deoxy and -fluorogalactosyl ceramides were synthesized, and their ability to stimulate iNKT cells, based on levels of IL-2 production, was assessed in three NKT cell receptor hybridomas. In two of the hybridomas, 1.2 and 2H4, all of the analogs were immunostimulatory, while in the 1.4 hybridoma only the 4″-fluoro analog led to the production of significant levels of IL-2.
- Raju, Ravinder,Castillo, Bernard F.,Richardson, Stewart K.,Thakur, Meena,Severins, Ryan,Kronenberg, Mitchell,Howell, Amy R.
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supporting information; experimental part
p. 4122 - 4125
(2010/04/29)
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- Characterization and mechanistic studies of DesII: A radical S-adenosyl-l-methionine enzyme involved in the biosynthesis of TDP-D-desosamine
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D-Desosamine (1) is a 3-(N,N-dimethylamino)-3,4,6-trideoxyhexose found in a number of macrolide antibiotics including methymycin (2), neomethymycin (3), pikromycin (4), and narbomycin (5) produced by Streptomyces venezuelae. It plays an essential role in
- Szu, Ping-Hui,Ruszczycky, Mark W.,Choi, Sei-Hyun,Yan, Feng,Liu, Hung-Wen
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scheme or table
p. 14030 - 14042
(2009/12/25)
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- Monosaccharide Derivatives as Anti-Inflammatory and/or Anti-Cancer Agents
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The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disorder herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases su
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Page/Page column 15
(2009/03/07)
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