Supporting Information
Supporting Information File 1: Experimental procedures for compounds 1, 2, 4–8, 12, 18–22, 25, 26, 28, 29, 31, 40–42, 44, 45, and 48–51, HRMS results for reaction of 51 with piperidine, cell culture conditions and MTT assay, crystallographic data for compounds 25, 28, 29, and 41, and dose-response curves. | ||
Format: PDF | Size: 905.4 KB | Download |
Supporting Information File 2: NMR spectra for compounds 1, 2, 4–8, 12, 18–22, 25, 26, 28, 29, 31, 40–46, and 48–51. | ||
Format: PDF | Size: 11.4 MB | Download |
Cite the Following Article
Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine
Štěpán Horník, Lucie Červenková Šťastná, Petra Cuřínová, Jan Sýkora, Kateřina Káňová, Roman Hrstka, Ivana Císařová, Martin Dračínský and Jindřich Karban
Beilstein J. Org. Chem. 2016, 12, 750–759.
https://doi.org/10.3762/bjoc.12.75
How to Cite
Horník, Š.; Červenková Šťastná, L.; Cuřínová, P.; Sýkora, J.; Káňová, K.; Hrstka, R.; Císařová, I.; Dračínský, M.; Karban, J. Beilstein J. Org. Chem. 2016, 12, 750–759. doi:10.3762/bjoc.12.75
Download Citation
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window
below.
Citation data in RIS format can be imported by all major citation management software, including EndNote,
ProCite, RefWorks, and Zotero.
Presentation Graphic
Picture with graphical abstract, title and authors for social media postings and presentations. | ||
Format: PNG | Size: 217.3 KB | Download |
Citations to This Article
Up to 20 of the most recent references are displayed here.
Scholarly Works
- Jevric, M.; Klepp, J.; Puschnig, J.; Lamb, O.; Sumby, C. J.; Greatrex, B. W. Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions. Beilstein journal of organic chemistry 2024, 20, 823–829. doi:10.3762/bjoc.20.74
- Hamala, V.; Ondrášková, K.; Červenková Šťastná, L.; Krčil, A.; Müllerová, M.; Kurfiřt, M.; Hiršová, K.; Holčáková, J.; Gyepes, R.; Císařová, I.; Bernášková, J.; Hrstka, R.; Karban, J. Improving the anticancer activity of fluorinated glucosamine and galactosamine analogs by attachment of a ferrocene or ruthenium tetrazene motif. Applied Organometallic Chemistry 2024, 38. doi:10.1002/aoc.7399
- Pollard, B.; Liu, X.; Connal, L. A.; Banwell, M. G.; Gardiner, M. G. The synthesis and manipulation of certain Diels–Alder adducts of levoglucosenone and iso-levoglucosenone. Australian Journal of Chemistry 2023, 76, 797–811. doi:10.1071/ch23130
- Wang, J.; Cao, W.; Zhang, W.; Dou, B.; Zeng, X.; Su, S.; Cao, H.; Ding, X.; Ma, J.; Li, X. Ac34FGlcNAz is an effective metabolic chemical reporter for O-GlcNAcylated proteins with decreased S-glyco-modification. Bioorganic chemistry 2022, 131, 106139. doi:10.1016/j.bioorg.2022.106139
- Huonnic, K.; Linclau, B. The Synthesis and Glycoside Formation of Polyfluorinated Carbohydrates. Chemical reviews 2022, 122, 15503–15602. doi:10.1021/acs.chemrev.2c00086
- Kaźmierczak, M.; Bilska-Markowska, M. Diethylaminosulfur Trifluoride (DAST) Mediated Transformations Leading to Valuable Building Blocks and Bioactive Compounds. European Journal of Organic Chemistry 2021, 2021, 5585–5604. doi:10.1002/ejoc.202101027
- Hazelard, D.; Compain, P. Nucleophilic Ring-Opening of 1,6-Anhydrosugars: Recent Advances and Applications in Organic Synthesis. European Journal of Organic Chemistry 2021, 2021, 3501–3515. doi:10.1002/ejoc.202100403
- Robert-Scott, G.; St-Gelais, J.; Giguère, D. Annulative Dimerization of Carbohydrates: Synthesis of Complex C2-Symmetrical 1,4-Dioxane-Sugar Hybrids. European Journal of Organic Chemistry 2021, 2021, 3322–3330. doi:10.1002/ejoc.202100411
- Hamala, V.; Šťastná, L. Č.; Kurfiřt, M.; Cuřínová, P.; Balouch, M.; Hrstka, R.; Voňka, P.; Karban, J. The effect of deoxyfluorination and O-acylation on the cytotoxicity of N-acetyl-D-gluco- and D-galactosamine hemiacetals. Organic & biomolecular chemistry 2021, 19, 4497–4506. doi:10.1039/d1ob00497b
- Hamala, V.; Šťastná, L. Č.; Kurfiřt, M.; Cuřínová, P.; Dračínský, M.; Karban, J. Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides. Beilstein journal of organic chemistry 2021, 17, 1086–1095. doi:10.3762/bjoc.17.85
- Kurfiřt, M.; Lucie, Č. Š.; Cuřínová, P.; Hamala, V.; Karban, J. Development of α-Selective Glycosylation for the Synthesis of Deoxyfluorinated TN Antigen Analogues. The Journal of organic chemistry 2021, 86, 5073–5090. doi:10.1021/acs.joc.0c03015
- Hevey, R. The role of fluorine in glycomimetic drug design. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 27, 2240–2253. doi:10.1002/chem.202003135
- St-Gelais, J.; Côté, É.; Lainé, D.; Johnson, P. A.; Giguère, D. Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 26, 13499–13506. doi:10.1002/chem.202002825
- Hamala, V.; Šťastná, L. Č.; Kurfiřt, M.; Cuřínová, P.; Dračínský, M.; Karban, J. Use of remote acyl groups for stereoselective 1,2-cis-glycosylation with fluorinated glucosazide thiodonors. Organic & biomolecular chemistry 2020, 18, 5427–5434. doi:10.1039/d0ob01065k
- Bilska-Markowska, M.; Szwajca, A.; Marciniak, B. Design, properties and applications of fluorinated and fluoroalkylated N-containing monosaccharides and their analogues. Journal of Fluorine Chemistry 2019, 227, 109364. doi:10.1016/j.jfluchem.2019.109364
- St-Gelais, J.; Bouchard, M.; Denavit, V.; Giguère, D. Synthesis and Lipophilicity of Trifluorinated Analogues of Glucose. The Journal of organic chemistry 2019, 84, 8509–8522. doi:10.1021/acs.joc.9b00795
- Malassis, J.; Vendeville, J.-B.; Nguyen, Q.-H.; Boujon, M.; Gaignard-Gaillard, Q.; Light, M. E.; Linclau, B. Synthesis of vicinal dideoxy-difluorinated galactoses. Organic & biomolecular chemistry 2019, 17, 5331–5340. doi:10.1039/c9ob00707e
- Uhrig, M. L.; Lantaño, B.; Postigo, A. Synthetic strategies for fluorination of carbohydrates. Organic & biomolecular chemistry 2019, 17, 5173–5189. doi:10.1039/c9ob00405j
- Kurfiřt, M.; Št’astná, L. Č.; Dračínský, M.; Müllerová, M.; Hamala, V.; Cuřínová, P.; Karban, J. Stereoselectivity in Glycosylation with Deoxofluorinated Glucosazide and Galactosazide Thiodonors. The Journal of organic chemistry 2019, 84, 6405–6431. doi:10.1021/acs.joc.9b00705
- Quiquempoix, L.; Wang, Z.; Graton, J.; Latchem, P. G.; Light, M. E.; Le Questel, J.-Y.; Linclau, B. Synthesis of 2,3,4-Trideoxy-2,3,4-trifluoroglucose. The Journal of organic chemistry 2019, 84, 5899–5906. doi:10.1021/acs.joc.9b00310
Patents
- YONG VOON WEE; LING CHANG-CHUN; STEPHENSON ERIN LAUREL; ZHANG PING; KEOUGH MICHAEL BRADLEY; RAWJI KHALIL SHERALI. Fluorinated N-acetyl glucosamine analogs and xylose derivatives. US 11365212 B2, June 21, 2022.
- YONG VOON WEE; LING CHANG-CHUN; STEPHENSON ERIN LAUREL; ZHANG PING; KEOUGH MICHAEL BRADLEY; RAWJI KHALIL SHERALI. FLUORINATED N-ACETYL GLUCOSAMINE ANALOGS AND XYLOSE DERIVATIVES. WO 2019227228 A1, Dec 5, 2019.
- YANG MENG; XU XIAOJIE; JING YATING. Preparation method of fondaparinux sodium monosaccharide intermediate. CN 109096348 A, Dec 28, 2018.