Preferences help
enabled [disable] Abstract
Number of results
2012 | 10 | 2 | 386-394
Article title

Synthesis of novel 3-deoxy-3-C-triazolylmethyl-allose derivatives and evaluation of their biological activity

Title variants
Languages of publication
Recently, monosaccharide-triazole conjugates have proved to possess a large variety of useful biological activities. This paper describes synthesis of a new series of 3-deoxy-3-C-triazolylmethyl-allose derivatives. These new compounds are obtained from acetonide-protected 3-deoxy-3-azidomethyl allose and commercial alkynes via Cu(I) catalyzed 1,3-dipolar cycloaddition. The obtained molecular scaffolds differ from those described earlier by the presence of a methylene linker (-CH2-) between the C(3) of allose and the triazole moiety. It was demonstrated that acetonide-protected monosaccharide, 3-deoxy-3-C-(4-phenyl-1H-1,2,3-triazol-1-yl)methyl-1,2:5,6-di-O-isopropylidene-α-d-allofuranose, inhibited α-L-fucosidase for 26% at 0.1 mM concentration, but a deprotected analog, 3-deoxy-3-C-(4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl)methyl-β-d-allofuranose, showed 15% inhibition of β-glucosidase at 1 mM concentration. [...]
Physical description
1 - 4 - 2012
29 - 1 - 2012
  • Faculty of Material Science and Applied Chemistry, Riga Technical University, LV-1007, Riga, Latvia
  • Department of Organic Chemistry, Faculty of Chemistry, University of Seville, 41012, Seville, Spain
  • Department of Organic Chemistry, Faculty of Chemistry, University of Seville, 41012, Seville, Spain
  • Faculty of Material Science and Applied Chemistry, Riga Technical University, LV-1007, Riga, Latvia
  • [1] V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem., Int. Ed. 41, 2596 (2002)<2596::AID-ANIE2596>3.0.CO;2-4[Crossref]
  • [2] C.W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 67, 3057 (2002)[Crossref]
  • [3] M. Meldal, C.W. Tornoe, Chem. Rev. 108, 2952 (2008)[Crossref]
  • [4] S. Poulsen, B.L. Wilkinson, A. Innocenti, D. Vullo, C.T. Supuran, Bioorg. Med. Chem. 18, 4624 (2008)[Crossref]
  • [5] L. Yang, W. Xu, F. Chen, L. Liu-Chen, Z. Ma, D.Y.W. Lee, Bioorg. Med. Chem. Lett. 19, 1301 (2009)[Crossref]
  • [6] J. Li, M. Zheng, W. Tang, P. He, W. Zhu, T. Li, J. Zuo, H. Liu, H. Jiang, Bioorg. Med. Chem. Lett. 16, 5009 (2006)[Crossref]
  • [7] F. Wuest, X. Tang, T. Kniess, J. Pietzsch, M. Suresh, Bioorg. Med. Chem. 17, 1146 (2009)[Crossref]
  • [8] G.C. Tron, T. Pirali, R.A. Billington, P.L. Canonico, G. Sorba, A.A. Genazzani, Med. Res. Rev. 28, 278 (2008)[Crossref]
  • [9] S. Dedola, S.A. Nepogodiev, R.A. Field, Org. Biomol. Chem. 5, 1006 (2007)[Crossref]
  • [10] A. Dondoni, Chem. Asian. J. 2, 700 (2007)[Crossref]
  • [11] V. Aragão-Leoneti, V.L. Campo, A.S. Gomes, R.A. Field, I. Carvalho, Tetrahedron 66, 9475 (2010)[Crossref]
  • [12] S. Dedola, D.L. Hughes, S.A. Nepogodiev, M. Rejzek, R.A. Field, Carbohydr. Res. 345, 1123 (2010)[Crossref]
  • [13] I. Carvalho, P. Andrade, V.L. Campo, P.M.M. Guedes, R. Sesti-Costa, J.S. Silva, S. Schenkman, S. Dedola, L. Hill, M. Rejzek, S.A. Nepogodiev, R.A. Field, Bioorg. Med. Chem. 18, 2412 (2010)[Crossref]
  • [14] E. Bokor, T. Docsa, P. Gergely, L. Somsak, Bioorg. Med. Chem. 18, 1171 (2010)[Crossref]
  • [15] B. Kumar Singh, Y.A. Kumar, B. Kumar, A. Gaikwad, S. Kumar Sinha, V. Chaturvedi, R. Pati Tripathi, Carbohydr. Res. 343, 1153 (2008)[Crossref]
  • [16] M. Ortega-Munoz, F. Perez-Balderas, J. Morales-Sanfrutos, F. Hernandez-Mateo, J. Isac-Garcia, F. Santoyo-Gonzalez, Eur. J. Org. Chem. 2009, 2454 (2009)[Crossref]
  • [17] J. Marco-Contelles, C.A. Jiménez, Tetrahedron 55, 10511 (1999)[Crossref]
  • [18] B.-Y. Lee, S.R. Park, H.B. Jeon, K.S. Kim, Tetrahedron Lett. 47, 5105 (2006)[Crossref]
  • [19] B.A. Salameh, H. Leffler, U.J. Nilsson, Bioorg. Med. Chem. Lett. 15, 3344 (2005)[Crossref]
  • [20] S.B. Ferreira, A.C.R. Sodero, M.F.C. Cardoso, E.S. Lima, C.R. Kaiser, F.P. Silva Jr., V.F. Ferreira, J. Med. Chem. 53, 2364 (2010)[Crossref]
  • [21] N. Anand, N. Jaiswal, S. Kumar Pandey, A.K. Srivastava, R.P. Tripathi, Carbohydr. Res. 346, 16 (2011)[Crossref]
  • [22] B.E. Maryanoff, J. Med. Chem. 52, 3431 (2009)[Crossref]
  • [23] D.G. Waller, A.G. Renwick, K. Hillier, Eds. Medical Pharmacology and Therapeutics, 2nd edition (Elsevier Saunders, London, 2005)
  • [24] B.E. Maryanoff, M.J. Costanzo, S.O. Nortey, M.N. Greco, R.P. Shank, J.J. Schupsky, M.P. Ortegon, J.L. Vaught, J. Med. Chem. 41, 1315 (1998)[Crossref]
  • [25] P.A. Petukhov, J. Zhang, C.Z. Wang, Y.P. Ye, K.M. Johnson, A.P. Kozikowski, J. Med. Chem. 47, 3009 (2004)[Crossref]
  • [26] M. Krier, J.X. de Araujo-Junior, M. Schmitt, J. Duranton, H. Justiano-Basaran, C. Lugnier, J.J. Bourguignon, D. Rognan, J. Med. Chem. 48, 3816 (2005)[Crossref]
  • [27] R. Saul, J.P. Chambers, R.J. Molyneux, A.D. Elbein, Arch. Biochem. Biophys. 221, 593 (1983)[Crossref]
  • [28] A. Brandi, S. Cicchi, F.M. Cordero, R. Frignoli, A. Goti, S. Picasso, P. Vogel, J. Org. Chem. 60, 6806 (1995)[Crossref]
  • [29] V.V. Filichev, E.B. Pedersen, Tetrahedron 57, 9163 (2001)[Crossref]
  • [30] M.M. Bio, F. Xu, M. Waters, J.M. Williams, K.A. Savary, C.J. Cowden, C. Yang, E. Buck, Z.J. Song, D.M. Tschaen, R.P. Volante, R.A. Reamer, E.J.J Grabowski, J. Org. Chem. 69, 6257 (2004)[Crossref]
  • [31] P. Ostrovskis, J. Mackeviča, V. Kumpiņš, M. Turks, In: G. van der Marel, J. Codee (Eds.), Carbohydrate Chemistry: Proven Methods, Volume 2 (CRC Press) submitted.
Document Type
Publication order reference
YADDA identifier
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.