- 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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- C-3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies
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To obtain key sugar derivatives for making homooligomeric foldamers or α/β-chimera peptides, economic and multigram scale synthetic methods were to be developed. Though described in the literature, the cost-effective making of both 3-amino-3-deoxy-ribofuranuronic acid (H–tX–OH) and its C-3 epimeric stereoisomer, the 3-amino-3-deoxy-xylofuranuronic acid (H–cX–OH) from d-glucose is described here. The present synthetic route elaborated is (1) appropriate for large-scale synthesis; (2) reagent costs reduced (e.g. by a factor of 400); (3) yields optimized are ~80% or higher for all six consecutive steps concluding –tX– or –cX– and (4) reaction times shortened. Thus, a new synthetic route step-by-step optimized for yield, cost, time and purification is given both for d-xylo and d-ribo-amino-furanuronic acids using sustainable chemistry (e.g. less chromatography with organic solvents; using continuous-flow reactor). Our study encompasses necessary building blocks (e.g. –X–OMe, –X–OiPr, –X–NHMe, Fmoc–X–OH) and key coupling reactions making –Aaa–tX–Aaa– or –Aaa–tX–tX–Aaa– type “inserts”. Completed for both stereoisomers of X, including the newly synthesized Fmoc–cX–OH, producing longer oligomers for drug design and discovery is more of a reality than a wish.
- Nagy, Adrienn,Csordás, Barbara,Zsoldos-Mády, Virág,Pintér, István,Farkas, Viktor,Perczel, András
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p. 223 - 240
(2017/02/05)
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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 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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- 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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Page/Page column 18
(2008/12/05)
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- MONOSACCHARIDE DERIVATIVES
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The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disclosed herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases s
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Page/Page column 11; 13
(2010/11/29)
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- Monosaccharide derivatives
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The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disclosed herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases s
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Page/Page column 16; 18
(2010/11/29)
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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 24-25
(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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Page/Page column 36-37
(2010/11/24)
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- Synthesis of isoaristeromycin from D-glucose
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Isoaristeromycin 1, an analogue of the nucleoside antibiotic aristeromycin, has been synthesized by the application of intermolecular nitrone cycloaddition (INC) reaction on a D-glucose derived substrate.
- Singha,Tripathi,Roy,Achari,Mandal
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p. 919 - 924
(2007/10/03)
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- N-azole substituted carbohydrates. Synthesis and transformations of 1- (3'-deoxy-1',2':5',6'-di-O-isopropylidene-α-D-glucofuranos-3'-yl)-azole derivatives
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The synthesis and chemical manipulation of some 1-(3'-deoxy-1',2':5',6'- di-O-isopropylidene-α-D-glucofuranos-3'-yl)-azole derivatives is described.
- Marco-Contelles, Jose,Jimenez
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p. 10511 - 10526
(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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- O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide
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Reaction of p-toluenesulfonyl cyanide or methanesulfonyl cyanide with alcohols in the presence of 1,8-diazabicyclo[5.4.0]under-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) gives sulfinates in good yield. A mechanistic scheme involving sulfinyl cyanates 9 and 21 is suggested.
- Barton, Derek H. R.,Jaszberenyi, Joseph Cs.,Theodorakis, Emmanouil A.
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p. 9167 - 9178
(2007/10/02)
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- SYNTHESIS OF CHIRAL β-ALKOXY-α,β-UNSATURATED KETONES
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The title compounds are synthesized in one-pot from the easily available sodium salts of unsymmetrical 1,3-dicarbonyl derivatives and chiral alkoxides.
- Lubineau, Andre,Malleron, Annie
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p. 1053 - 1054
(2007/10/02)
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- REACTIONS OF HYDROXYL GROUPS WITH TOSYLCHLORIDE-DIMETHYLAMINOPYRIDINE SYSTEM. DIRECT SYNTHESIS OF CHLORIDES FROM HYDROXYCOMPOUNDS.
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The reactions of various hydroxyl groups with tosylchloride-dimethylaminopyridine system were investigated and direct synthesis of allyl, alkyl and glycosyl chlorides are described.
- Hwang, C. K.,Li, W. S.,Nicolau, K. C.
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p. 2295 - 2296
(2007/10/02)
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- Sugar Tosylates via p-Toluenesulfinic Acid Esters. - p-Toluenesulfinimidazolide - A Reagent for Formation of Sulfinic Acid Esters without Using Halides
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The reaction of the protected sugar derivatives 1, 4, 7, 10, 13, 16, 19 and 20 with p-toluenesulfinimidazolide prepared from p-toluenesulfinic acid and N,N'-carbonyldiimidazole yields the corresponding p-toluenesulfinic esters 2, 5, 8, 11, 14, 17, 20 and 22.With the exception of 20 and 22, these products can be oxidized with m-chloroperbenzoic acid in high yields and short overall reaction times to the tosylates 3, 6, 9, 12, 15 and 18.
- Redlich, Hartmut,Meyer, Wolf-Ulrich
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p. 1354 - 1360
(2007/10/02)
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- Alkyloxytris(dimethylamino)phosphonium Salts. Part 21. Anomeric Hydroxy-group Activation of 2,3:4,6-Di-O-isopropylidene-α-D-mannopyranose, Thioglycosylation and Glycosylation
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The action of carbon tetrachloride and tris(dimethylamino)phosphine at low temperature on 2,3:4,6-di-O-isopropylidene-α-D-mannopyranose affords the α anomeric form of the corresponding alkoxytris(dimethylamino)phosphonium chloride.The condensation of arom
- Chretien, Francoise,Chapleur, Yves,Castro, Bertrand,Gross, Bernard
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p. 381 - 384
(2007/10/02)
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