- New derivatives of levoglucosan by tandem epoxide allyl alcohol rearrangement-cuprate cross-coupling
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The alkylated allyl alcohols 6a, 7, and 8 (R = Me, Et, nBu) were formed in the reaction of the Cerny epoxide 3 with the Cyano-Gilman cuprates. The one-pot reaction was initiated by base-catalyzed epoxide allyl alcohol rearrangement to compound 5, followed
- Krohn, Karsten,Gehle, Dietmar,Floerke, Ulrich
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- Skipped Fluorination Motifs: Synthesis of Building Blocks and Comparison of Lipophilicity Trends with Vicinal and Isolated Fluorination Motifs
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Given there is an optimal lipophilicity range for orally bioavailable drugs, structural modifications applied in the drug development process are not only focused on optimizing bioactivity but also on fine-tuning lipophilicity. Fluorine introduction can b
- Troup, Robert I.,Jeffries, Benjamin,Saudain, Raphael El-Bekri,Georgiou, Eleni,Fish, Johanna,Scott, James S.,Chiarparin, Elisabetta,Fallan, Charlene,Linclau, Bruno
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p. 1882 - 1900
(2021/02/03)
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- Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects
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In this work, we synthesized all mono-, di-, and trifluorinated glucopyranose analogues at positions C-2, C-3, C-4, and C-6. This systematic investigation allowed us to perform direct comparison of 19F resonances of fluorinated glucose analogues and also to determine their lipophilicities. Compounds with a fluorine atom at C-6 are usually the most hydrophilic, whereas those with vicinal polyfluorinated motifs are the most lipophilic. Finally, the solvation energies of fluorinated glucose analogues were assessed for the first time by using density functional theory. This method allowed the log P prediction of fluoroglucose analogues, which was comparable to the C log P values obtained from various web-based programs.
- St-Gelais, Jacob,C?té, émilie,Lainé, Danny,Johnson, Paul A.,Giguère, Denis
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supporting information
p. 13499 - 13506
(2020/10/02)
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- Easy access to a carbohydrate-based template for stimuli-responsive surfactants
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In this paper we describe the synthesis of a new carbohydrate-based building block functionalized with azido or amino groups on the 2 and 4 positions. The building block can be synthesized in anomerically pure form in only five scalable steps starting fro
- Holmstr?m, Thomas,Pedersen, Christian Marcus,Raydan, Daniel
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supporting information
p. 2788 - 2794
(2020/12/28)
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- Exploring the Chemistry of Non-sticky Sugars: Synthesis of Polyfluorinated Carbohydrate Analogues of d-Allopyranose
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There is a growing interest in the preparation of polyfluorinated carbohydrates. A limited number of fluorohexopyranosides have been used in biological investigations because of the synthetic challenge they present. Hence, we report the synthesis of fluor
- Denavit, Vincent,St-Gelais, Jacob,Tremblay, Thomas,Giguère, Denis
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supporting information
p. 9272 - 9279
(2019/07/05)
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- THIENOPYRIMIDINE DERIVATIVE AND USE THEREOF IN MEDICINE
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The present invention relates to a thienopyrimidine derivative and use thereof in medicine, and also to a pharmaceutical composition containing the compound. The compound or pharmaceutical composition is used for inhibiting acetyl-CoA carboxylase (ACC). The present invention also relates to a method of preparing such compound and pharmaceutical composition, as well as their use in the treatment or prevention of diseases regulated by acetyl-CoA carboxylase in mammals, especially in humans.
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Paragraph 00318
(2018/08/12)
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- Synthesis of Protected 3-Deoxy-3-fluoro- and 4-Deoxy-4-fluoro-d-galactopyranosides from Levoglucosan
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Fluorinated carbohydrates are invaluable tools to study various biochemical processes. Herein, we describe a new strategy to access orthogonally protected 3-deoxy-3-fluorogalactopyranose and acetylated 4-deoxy-4-fluorogalactopyranose. Starting from inexpensive levoglucosan, most reactions were performed on a gram scale and allowed excellent regio- and stereocontrol with a minimal use of protection/deprotection cycles. Hence, we developed practical alternatives to the decade-long reported method to access both 3-deoxy-3-fluoro- and 4-deoxy-4-fluorogalactopyranose.
- Lainé, Danny,Denavit, Vincent,Giguère, Denis
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supporting information
p. 4986 - 4992
(2017/05/12)
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- Synthesis and glycosidase inhibitory activity of noeurostegine - A new and potent inhibitor of β-glucoside hydrolases
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A new, stable hemi-aminal nor-tropane christened noeurostegine was synthesised in 22 steps from levoglucosan and tested for inhibitory activity against glycoside hydrolases. Sweet almond and Thermotoga maritimaβ- glucosidases, coffee bean α-galactosidase,
- Rasmussen, Tina Secher,Jensen, Henrik Helligso
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supporting information; experimental part
p. 433 - 441
(2010/02/16)
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- Dioxabicyclooctanyl naphthalenenitriles as nonredox 5-lipoxygenase inhibitors: Structure-activity relationship study directed toward the improvement of metabolic stability
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Naphthalenic lignan lactone 3a (L-702,539), a potent and selective 5- 1ipoxygenase (5-LO) inhibitor, is extensively metabolized at two different sites: the tetrahydropyran and the lactone rings. Early knowledge of the metabolic pathways triggered and directed a structure-activity relationship study aimed toward the improvement of metabolic stability in this series. The best modifications discovered, i.e., replacement of the lactone ring by a nitrile group, replacement of the tetrahydropyran ring by a 6,8- dioxabicyclo[3.2.1]octanyl moiety, and replacement of the pendant phenyl ring by a 3-furyl ring, were incorporated in a single molecule to produce inhibitor 9ac (L-708,780). Compound 9ac inhibits the oxidation of arachidonic acid to 5-hydroperoxyeicosatetraenoic acid by 5-LO (IC50 = 190 nM) and the formation of leukotriene B4 in human polymorphonuclear leukocytes (IC50 = 3 nM) as well as in human whole blood (IC50 = 150 nM). The good inhibitory profile shown by naphthalenenitrile 9ac is accompanied by an improved resistance to oxidative metabolism. In addition, 9ac is orally active in the functional model of antigen-induced bronchoconstriction in allergic squirrel monkeys (95% inhibition at 0.1 mg/kg).
- Delorme, Daniel,Ducharme, Yves,Brideau, Christine,Chan, Chi-Chung,Chauret, Nathalie,Desmarais, Sylvie,Dubé, Daniel,Falgueyret, Jean-Pierre,Fortin, Réjean,Guay, Jocelyne,Hamel, Pierre,Jones, Tom R.,Lépine, Carole,Li, Chun,McAuliffe, Malia,McFarlane, Cyril S.,Nicoll-Griffith, Deborah A.,Riendeau, Denis,Yergey, James A.,Girard, Yves
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p. 3951 - 3970
(2007/10/03)
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- MEVINIC ACIDS AND ANALOGS : A NOVEL EFFICIENT ROUTE TO CHIRAL SYNTHONS FROM 1,6-ANHYDRO-D-GLUCOSE
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1,6-anhydro-D-glucose is efficiently and regioselectively deoxygenated at C-2 and C-4 by displacement of the corresponding ditosylate with thiophenol followed by Raney Ni hydrogenolysis.This route provides a short access to chirons of the key lactonic moi
- David, C.,Gesson, J.P.,Jacquesy, J.C.
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p. 6015 - 6018
(2007/10/02)
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- The Chemistry of Spiroacetals. Preparation of a Chiral Disubstituted Lactone Derivative; a Key Intermediate for Synthesis of the Spiroacetal Moieties of the Avermectins and Milbemycins
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A synthesis of two diprotected (4S,6S)-4-hydroxy-6-hydroxymethyltetrahydropyran-2-ones has been developed from laevoglucosan; reaction of these lactones with a substituted lithium acetylide derivative followed by hydrogenation and acid catalysed cyclisati
- Baker, Raymond,Boyes, R. Hugh O.,Broom, D. Mark P.,Devlin, J. Alastair,Swain, Christopher J.
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p. 829 - 831
(2007/10/02)
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- 1H NMR STUDY OF 1,6-ANHYDRO-β-D-GLUCOPYRANOSE TOSYLATED AT 2- AND/OR 4-POSITION
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The 1H nmr spectra of 1,6-anhydro-2-O-tosyl-, 1,6-anhydro-4-O-tosyl and 1,6-anhydro-2,4-di-O-tosyl-β-D-glucopyranose have been analyzed.The data allow to discriminate between the two monosubstituted levoglucosans.
- Rijsbergen, Ronan Van,Anteunis, Marc J. O.,Bruyn, Andre De
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p. 297 - 300
(2007/10/02)
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