- Gabriel-Cromwell aziridination of amino sugars; chiral ferrocenoyl-aziridinyl sugar synthesis and their biological evaluation
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N-sugar substituted chiral aziridines were synthesized via Gabriel-Cromwell reaction. Novel pure diastereomers of aziridine derivatives (4 diastereomers) were readily obtained in high yields and their structures were confirmed by means of 1H NM
- Sert, Mustafa,I??lar, ?zer,Yaglioglu, Ayse Sahin,Bulut, Adnan
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- Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone
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A series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, 1H NMR, 13C NMR, FT-IR, HRMS, optical rotation, and melting points. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. The compounds 9, 11 and 12 showed better activities at 25 μM against PC3 cell line with respect to the standard 5-fluorouracil (5-FU). Especially, the compounds 9 and 11 showed higher activities than the standard 5-FU even at low concentration (5 μM) against HeLa cell line. IC50 results also confirm these activities. The compounds 9, 10 and 11 have the IC50 values of 1.10 μM, 1.51 μM and 1.02 μM, respectively while 5-FU has 2.51 μM. Moreover, their cytotoxicity tests have proven that their viabilities were in between 50% and 100%.
- Arat, Esra,Bulut, Adnan,Demirta?, ?brahim,I??lar, ?zer,Sahin Yaglioglu, Ayse,Türk, Mustafa
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- A method for preparing N-alkylated kanosamines from diacetone D-glucose
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The aminoglycoside (AG) antibiotics have seen a resurgence in their clinical use given the increase in multi drug resistant bacterial infections. Campaigns to generate novel analogs show promise that structural modification can lead to compounds with improved pharmacological properties. The results described herein include a new method to synthesize mono-, di-, and mixed N-alkylated kanosamine sugars and their elaboration into novel glycosides that inhibit bacterial protein synthesis in vitro.
- Cannone, Zachary P.,Peczuh, Mark W.
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p. 1830 - 1833
(2019/06/19)
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- 2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination
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A series of 10 new carbohydrate-substituted bipyridines were prepared from 2,2′-bipyridine-3,3′-dicarboxylic acid, itself easily available from ortho-phenanthroline. As a preliminary exploration of their use as chiral ligands, Cu(II)-catalysed asymmetric electrophilic fluorination of model β-ketoesters using these simple and easily accessible chiral bipyridines was studied. Only modest enantioselectivity was observed in this reaction, although the ee was in a similar range as those provided by known and more elaborate ligands.
- Assalit, Aurelie,Billard, Thierry,Chambert, Stephane,Langlois, Bernard R.,Queneau, Yves,Coe, Diane
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body text
p. 593 - 601
(2009/09/05)
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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 17
(2009/03/07)
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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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- MONOSACCHARIDE DERIVATIVES
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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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- 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 25
(2010/11/28)
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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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- Kanosamine biosynthesis: A likely source of the aminoshikimate pathway's nitrogen atom
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The biosynthetic source of the nitrogen atom incorporated into the aminoshikimate pathway has remained a question for some time. 3-Amino-3-deoxy-d-fructose 6-phosphate has previously been demonstrated to be a precursor to 4-amino-3,4-dideoxy-d-arabino-heptulosonic acid 7-phosphate and 3-amino-5-hydroxybenzoic acid via the inferred intermediacy of 1-deoxy-1-imino-d-erythrose 4-phosphate in Amycolatopsis mediterranei cell-free extract. This investigation examines the possibility that the natural product kanosamine might be a precursor to 3-amino-3-deoxy-d-fructose 6-phosphate. Kanosamine 6-phosphate was synthesized by a chemoenzymatic route and incubated in A. mediterranei cell-free lysate along with d-ribose 5-phosphate and phosphoenolpyruvate. Formation of 4-amino-3,4-dideoxy-d-arabino-heptulosonic acid 7-phosphate and 3-amino-5-hydroxybenzoic acid was observed. Subsequent incubation in A. mediterranei cell-free lysate of glutamine and NAD with UDP-glucose resulted in the formation of kanosamine. The bioconversion of UDP-glucose into kanosamine along with the bioconversion of kanosamine 6-phosphate into 4-amino-3,4-dideoxy-d-arabino-heptulosonic acid 7-phosphate and 3-amino-5-hydroxybenzoic acid suggests that kanosamine biosynthesis is the source of the aminoshikimate pathway's nitrogen atom. Copyright
- Guo, Jiantao,Frost
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p. 10642 - 10643
(2007/10/03)
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- A novel, simple, chemoseleetive and practical protocol for the reduction of azides using In/NH4Cl
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A simple, mild and efficient method for the reduction of azides to amines using In/NH4Cl is described.
- Reddy, G. Vidyasagar,Rao, G. Venkat,Iyengar
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p. 3937 - 3938
(2007/10/03)
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- The use of a new magnesium-derived hydride reagent for carbohydrate derivatives
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The magnesium hydride based reagent in THF solution is an excellent tool for the stereoselective reduction of different uloside derivatives. Sugar azides, sulfonyl esters give aminosugars and methylose derivatives without affecting other functionalities. Halogenated sugars or methylene derivatives are stable under these conditions. The reagent can be applied in the presence of a wide variety of blocking groups (acetals, benzyl and allyl ethers, imides, C=C bonds) generally used in the carbohydrate chemistry.
- Szabovik,Medgyes,Antal,Varga,Knott,Liptak
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p. 1003 - 1009
(2007/10/03)
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- The invention of radical reactions. 30. Diazirines as carbon radical traps. Mechanistic aspects and synthetic applications of a novel and efficient amination process
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A number of diazirines were synthesized for the purpose of exploring the addition of a carbon radical to the nitrogen-nitrogen double bond. Carbon radicals, generated from the photolysis of the O-acyl derivatives of N-hydroxy-2-thiopyridone or via radical exchange from the corresponding organotellurides, were shown to add smoothly to the diazirines leading to imines 34. When 3-(trifluoromethyl)-3-phenyldiazirine (13) is used as the trap, the thus formed imines can be easily hydrolyzed to amines. A mechanism that involves dimerization of the diaziridinyl radicals 32 to produce tetraazo intermediates 33 is suggested in accord with variable temperature NMR data for the reaction. Proof for this mechanistic scheme was furthermore obtained by isolation and X-ray structure determination of 33d. The first X-ray structure of a 3-(trifluoromethyl)-3-aryldiazirine is also reported.
- Barton, Derek H. R.,Jaszberenyi, Joseph Cs.,Theodorakis, Emmanouil A.,Reibenspies
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p. 8050 - 8059
(2007/10/02)
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- SELECTIVE HYDROGENATION OF ORGANIC AZIDES TO AMINES BY INTERLAMELLAR MONTMORILLONITEDIPHENYLPHOSPHINE PALLADIUM(II) CATALYST
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Organic azides are selectively and catalytically hydrogenated to amines by a heterogenized homogeneous catalyst for the first time.
- Sharma, G. V. M.,Chandrasekhar, S.
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p. 3289 - 3294
(2007/10/02)
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- NEW SYNTHETIC "TRICKS". (Et3NH)(Sn(SPh)3) AND Bu2SnH2, TWO USEFUL REAGENTS FOR THE REDUCTION OF AZIDES TO AMINES
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Treatment of Sn(SPh)2 with PhSH and Et3N affords a tin(II) complex, soluble in organic solvents, wich is the best reducing agent for azides reported so far.Bu2SnH2, although not so reactive, also shows several advantages with regard to the standard reducing agents for azides, such as its solubility in most solvents or its scarce reactivity with water.
- Bartra, Marti,Urpi, Felix,Vilarrasa, Jaume
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p. 5941 - 5944
(2007/10/02)
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- A New Efficient Access to Aminodeoxy Sugars
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A mild and convenient synthesis of aminodeoxy sugars is described, involving the esterification of partially protected carbohydrates with trifluoromethanesulphonic anhydride and the reaction of the resulting trifluoromethanesulphonates with ammonia; the d
- Malik, Abdul,Afza, Nighat,Roosz, Michael,Voelter, Wolfgang
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p. 1530 - 1531
(2007/10/02)
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- Synthesis and Reactions of 3-O-Phosphoniogluco- and Allofuranoses
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Starting from the bicyclic gluco- (3,5,7, and 9) and allofuranoses 11 the isolable 3-O-phosphoniocarbohydrates (4,6,8,10, and 12) were synthesized by reaction with triphenylphosphane (1), diethyl azodicarboxylate (2), and alkylating or acylating agents.On heating, the various allo configurated salts 12 are converted into the corresponding at C-3 epimeric gluco configurated substitution products offering a wide range of flexibility.The reactions of the gluco configurated salts depend strongly on the type of nucleophile to be introduced and from neighboring groups in t he carbohydrate skeleton.The iodide 4a and the azide 4g react by substitution forming the allo derivatives 15.In contrast, bromide, chloride, and sulfonate as gegen-ions mainly cause rearrangement of the 5,6-isopropylidene bridge or opening of the 5,6-anhydro structure.
- Kunz, Horst,Schmidt, Peter
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p. 1245 - 1260
(2007/10/02)
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