Preparation of selectively protected protoescigenin derivatives for synthesis of escin analogs and neoglycoconjugates

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• 作者：Kamil Jatczak (1)
  Mariusz Gruza (1)
  Katarzyna Filip (1)
  Piotr Cmoch (1) (2)
  Grzegorz Grynkiewicz (1)
  
• 关键词：Horse chestnut saponins and sapogenins ; Protoescigenin derivatization ; Click chemistry
• 刊名：Central European Journal of Chemistry
• 出版年：2014
• 出版时间：December 2014
• 年：2014
• 卷：12
• 期：12
• 页码：1222-1231
• 全文大小：
• 参考文献：1. H. Lachance, S. Wetzel, K. Kumar, H. Waldmann, J. Med. Chem. 55, 5989 (2012) CrossRef
  2. R. Bade, H.-F. Chan, J. Reynisson, Eur. J. Med. Chem. 45, 5646 (2010) CrossRef
  3. H. Zaid, J. Raiyn, A. Nasser, B. Saad, A. Rayan, Open Nutraceuticals J. 3, 194 (2010)
  4. P. Ertl, S. Roggo, A. Schuffenhauer, J. Chem. Inf. Model. 48, 68 (2007) CrossRef
  5. S.M. Jachak, A. Saklani, Curr Sci 92, 1251 (2007)
  6. M.M. Adams, P. Damani, N.R. Perl, A. Won, F. Hong, P.O. Livingston, G. Ragupathi, D.Y. Gin, J. Am. Chem. Soc. 132, 1939 (2010) CrossRef
  7. G. Ragupathi, P. Damani, K. Deng, M.M. Adams, J. Hang, C. George, P.O. Livingston, D.Y. Gin, Vaccine 28, 4260 (2010) CrossRef
  8. H.-X. Sun, Y. Xie, Y.-P. Ye, Vaccine 27, 1787 (2009) CrossRef
  9. H. Sheng, H. Sun, Nat. Prod. Rep. 28, 543 (2011) CrossRef
  10. A. Salminen, M. Lehtonen, T. Suuronen, K. Kaarniranta, J. Huuskonen, Cell. Mol. Life Sci. 65, 2979 (2008) CrossRef
  11. P. Dzubak, M. Hajduch, D. Vydra, A. Hustova, M. Kvasnica, D. Biedermann, L. Markova, M. Urban, J. Sarek, Nat. Prod. Rep. 23, 394 (2006) CrossRef
  12. M.M. Gruza, K. Jatczak, B. Zagrodzki, M. 艁aszcz, K. Koziak, M. Mali艅ska, P. Cmoch, T. Giller, O. Zegrocka-Stendel, K. Wo藕niak, G. Grynkiewicz, Molecules 18, 4389 (2013) CrossRef
  13. C.R. Sirtori, Pharmacol. Res. 44, 183 (2001) CrossRef
  14. EMEA Committee on Herbal Medicinal Products, Assessment Report on / Aesculus Hippocastanum L., semen, EMEA/HMPC/225304/2008, 1 (2009)
  15. R. Tschesche, G. Wulff, Fortschr. Chem. Org. Naturst. 30, 461 (1973)
  16. Z. Zhang, S. Li, X.-Y. Lian, Pharm. Crops 1, 24 (2010) CrossRef
  17. C.D. Hein, X.-M. Liu, D. Wang, Pharm. Res. 25, 2216 (2008) CrossRef
  18. M. Meldal, C. W. Torn酶e, Chem. Rev. 108, 2952 (2008) CrossRef
  19. G. Grynkiewicz, I. Fokt, P. Skibicki, T. Przew艂oka, W. Szeja, W. Priebe, Pol. J Chem, 79, 335 (2005)
  20. W. Priebe, I. Fokt, T. Przewloka, M. Krawczyk, P. Skibicki, G. Grynkiewicz, R. Perez-Soler, US 2005004048 A1 (filed 2004.01.06.)
  21. L. Daley, Y. Guminski, P. Demerseman, A. Kruczynski, C. Eti茅vant, T. Imbert, B.T. Hill, C. Monneret, J. Med. Chem. 41, 4475 (1998) CrossRef
  22. A. Banaszek, K. Krowicki, A. Zamojski, J. Chromatogr. A. 32, 581 (1968) CrossRef
  23. M.C. Pirrung, The Synthetic Organic Chemist鈥檚 Companion (John Wiley & Sons, Inc., Hoboken, 2006) pp. 171鈥?72
  
• 作者单位：Kamil Jatczak (1)
  Mariusz Gruza (1)
  Katarzyna Filip (1)
  Piotr Cmoch (1) (2)
  Grzegorz Grynkiewicz (1)
  
  1. Pharmaceutical Research Institute, 01-793, Warsaw, Poland
  2. Institute of Organic Chemistry Polish Academy of Sciences, 01-224, Warsaw, Poland
  
• ISSN：1644-3624

文摘

Protoescigenin, the main aglycone of horse chestnut saponin mixture known as escin, was selected as substrate for exploratory chemistry towards selective protection, followed by propargyl ether formation and subsequent condensation with azido-monosaccharides, to obtain novel triazole linked conjugates of the triterpene.