20204-80-2Relevant articles and documents
New derivatives of levoglucosan by tandem epoxide allyl alcohol rearrangement-cuprate cross-coupling
Krohn, Karsten,Gehle, Dietmar,Floerke, Ulrich
, p. 2841 - 2848 (2005)
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
Skipped Fluorination Motifs: Synthesis of Building Blocks and Comparison of Lipophilicity Trends with Vicinal and Isolated Fluorination Motifs
Troup, Robert I.,Jeffries, Benjamin,Saudain, Raphael El-Bekri,Georgiou, Eleni,Fish, Johanna,Scott, James S.,Chiarparin, Elisabetta,Fallan, Charlene,Linclau, Bruno
, p. 1882 - 1900 (2021/02/03)
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
Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects
St-Gelais, Jacob,C?té, émilie,Lainé, Danny,Johnson, Paul A.,Giguère, Denis
supporting information, p. 13499 - 13506 (2020/10/02)
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.
Easy access to a carbohydrate-based template for stimuli-responsive surfactants
Holmstr?m, Thomas,Pedersen, Christian Marcus,Raydan, Daniel
supporting information, p. 2788 - 2794 (2020/12/28)
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
Exploring the Chemistry of Non-sticky Sugars: Synthesis of Polyfluorinated Carbohydrate Analogues of d-Allopyranose
Denavit, Vincent,St-Gelais, Jacob,Tremblay, Thomas,Giguère, Denis
supporting information, p. 9272 - 9279 (2019/07/05)
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
THIENOPYRIMIDINE DERIVATIVE AND USE THEREOF IN MEDICINE
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Paragraph 00318, (2018/08/12)
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.
Synthesis of Protected 3-Deoxy-3-fluoro- and 4-Deoxy-4-fluoro-d-galactopyranosides from Levoglucosan
Lainé, Danny,Denavit, Vincent,Giguère, Denis
supporting information, p. 4986 - 4992 (2017/05/12)
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.
Synthesis and glycosidase inhibitory activity of noeurostegine - A new and potent inhibitor of β-glucoside hydrolases
Rasmussen, Tina Secher,Jensen, Henrik Helligso
supporting information; experimental part, p. 433 - 441 (2010/02/16)
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,
Dioxabicyclooctanyl naphthalenenitriles as nonredox 5-lipoxygenase inhibitors: Structure-activity relationship study directed toward the improvement of metabolic stability
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
, p. 3951 - 3970 (2007/10/03)
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).