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

• Autorzy: Kamil Jatczak , Mariusz Gruza , Katarzyna Filip , Piotr Cmoch , Grzegorz Grynkiewicz
• Języki publikacji: EN

Abstrakty

EN

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.

Słowa kluczowe

EN

Horse chestnut saponins and sapogenins   Protoescigenin derivatization   Click chemistry  

• Czasopismo: Open Chemistry
• Rocznik: 2014
• Tom: 12
• Numer: 12
• Strony: 1222-1231

Daty

wydano

2014-12-01

online

2014-06-07

Twórcy

autor

Kamil Jatczak

• Pharmaceutical Research Institute

autor

Mariusz Gruza

• Pharmaceutical Research Institute

autor

Katarzyna Filip

• Pharmaceutical Research Institute

autor

Piotr Cmoch

autor

Grzegorz Grynkiewicz

• Pharmaceutical Research Institute,

Bibliografia

• [1] H. Lachance, S. Wetzel, K. Kumar, H. Waldmann, J. Med. Chem. 55, 5989 (2012) http://dx.doi.org/10.1021/jm300288g[Crossref]
• [2] R. Bade, H.-F. Chan, J. Reynisson, Eur. J. Med. Chem. 45, 5646 (2010) http://dx.doi.org/10.1016/j.ejmech.2010.09.018[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) http://dx.doi.org/10.1021/ci700286x[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) http://dx.doi.org/10.1021/ja9082842[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) http://dx.doi.org/10.1016/j.vaccine.2010.04.034[Crossref]
• [8] H.-X. Sun, Y. Xie, Y.-P. Ye, Vaccine 27, 1787 (2009) http://dx.doi.org/10.1016/j.vaccine.2009.01.091[Crossref]
• [9] H. Sheng, H. Sun, Nat. Prod. Rep. 28, 543 (2011) http://dx.doi.org/10.1039/c0np00059k[Crossref]
• [10] A. Salminen, M. Lehtonen, T. Suuronen, K. Kaarniranta, J. Huuskonen, Cell. Mol. Life Sci. 65, 2979 (2008) http://dx.doi.org/10.1007/s00018-008-8103-5[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) http://dx.doi.org/10.1039/b515312n[Crossref]
• [12] M.M. Gruza, K. Jatczak, B. Zagrodzki, M. Łaszcz, K. Koziak, M. Malińska, P. Cmoch, T. Giller, O. Zegrocka-Stendel, K. Woźniak, G. Grynkiewicz, Molecules 18, 4389 (2013) http://dx.doi.org/10.3390/molecules18044389[Crossref]
• [13] C.R. Sirtori, Pharmacol. Res. 44, 183 (2001) http://dx.doi.org/10.1006/phrs.2001.0847[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) http://dx.doi.org/10.2174/2210290601001010024[Crossref]
• [17] C.D. Hein, X.-M. Liu, D. Wang, Pharm. Res. 25, 2216 (2008) http://dx.doi.org/10.1007/s11095-008-9616-1[Crossref]
• [18] M. Meldal, C. W. Tornøe, Chem. Rev. 108, 2952 (2008) http://dx.doi.org/10.1021/cr0783479[Crossref]
• [19] G. Grynkiewicz, I. Fokt, P. Skibicki, T. Przewłoka, 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. Etiévant, T. Imbert, B.T. Hill, C. Monneret, J. Med. Chem. 41, 4475 (1998) http://dx.doi.org/10.1021/jm9800752[Crossref]
• [22] A. Banaszek, K. Krowicki, A. Zamojski, J. Chromatogr. A. 32, 581 (1968) http://dx.doi.org/10.1016/S0021-9673(01)80531-8[Crossref]
• [23] M.C. Pirrung, The Synthetic Organic Chemist’s Companion (John Wiley & Sons, Inc., Hoboken, 2006) pp. 171–172

Identyfikatory

DOI

10.2478/s11532-014-0572-9