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

• Authors: Jekaterina Rjabova , Vitālijs Rjabovs , Antonio Moreno Vargas , Elena Clavijo , Māris Turks
• Languages of publication: EN

Abstracts

EN

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. [...]

Keywords

EN

3-deoxy-3-C-triazolylmethyl-allose; Methylene linker; Triazolyl-monosaccharides; Click chemistry; Inhibitors of glycosidases

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2012
• Volume: 10
• Issue: 2
• Pages: 386-394

Dates

published

1 - 4 - 2012

online

29 - 1 - 2012

Contributors

author

Jekaterina Rjabova

author

Vitālijs Rjabovs

• Faculty of Material Science and Applied Chemistry, Riga Technical University, LV-1007, Riga, Latvia

author

Antonio Moreno Vargas

• Department of Organic Chemistry, Faculty of Chemistry, University of Seville, 41012, Seville, Spain

author

Elena Clavijo

• Department of Organic Chemistry, Faculty of Chemistry, University of Seville, 41012, Seville, Spain

author

Māris Turks

• Faculty of Material Science and Applied Chemistry, Riga Technical University, LV-1007, Riga, Latvia

References

• [1] V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem., Int. Ed. 41, 2596 (2002) http://dx.doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4[Crossref]
• [2] C.W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 67, 3057 (2002) http://dx.doi.org/10.1021/jo011148j[Crossref]
• [3] M. Meldal, C.W. Tornoe, Chem. Rev. 108, 2952 (2008) http://dx.doi.org/10.1021/cr0783479[Crossref]
• [4] S. Poulsen, B.L. Wilkinson, A. Innocenti, D. Vullo, C.T. Supuran, Bioorg. Med. Chem. 18, 4624 (2008) http://dx.doi.org/10.1016/j.bmcl.2008.07.010[Crossref]
• [5] L. Yang, W. Xu, F. Chen, L. Liu-Chen, Z. Ma, D.Y.W. Lee, Bioorg. Med. Chem. Lett. 19, 1301 (2009) http://dx.doi.org/10.1016/j.bmcl.2009.01.078[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) http://dx.doi.org/10.1016/j.bmcl.2006.07.047[Crossref]
• [7] F. Wuest, X. Tang, T. Kniess, J. Pietzsch, M. Suresh, Bioorg. Med. Chem. 17, 1146 (2009) http://dx.doi.org/10.1016/j.bmc.2008.12.032[Crossref]
• [8] G.C. Tron, T. Pirali, R.A. Billington, P.L. Canonico, G. Sorba, A.A. Genazzani, Med. Res. Rev. 28, 278 (2008) http://dx.doi.org/10.1002/med.20107[Crossref]
• [9] S. Dedola, S.A. Nepogodiev, R.A. Field, Org. Biomol. Chem. 5, 1006 (2007) http://dx.doi.org/10.1039/b618048p[Crossref]
• [10] A. Dondoni, Chem. Asian. J. 2, 700 (2007) http://dx.doi.org/10.1002/asia.200700015[Crossref]
• [11] V. Aragão-Leoneti, V.L. Campo, A.S. Gomes, R.A. Field, I. Carvalho, Tetrahedron 66, 9475 (2010) http://dx.doi.org/10.1016/j.tet.2010.10.001[Crossref]
• [12] S. Dedola, D.L. Hughes, S.A. Nepogodiev, M. Rejzek, R.A. Field, Carbohydr. Res. 345, 1123 (2010) http://dx.doi.org/10.1016/j.carres.2010.03.041[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) http://dx.doi.org/10.1016/j.bmc.2010.02.053[Crossref]
• [14] E. Bokor, T. Docsa, P. Gergely, L. Somsak, Bioorg. Med. Chem. 18, 1171 (2010) http://dx.doi.org/10.1016/j.bmc.2009.12.043[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) http://dx.doi.org/10.1016/j.carres.2008.02.013[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) http://dx.doi.org/10.1002/ejoc.200801169[Crossref]
• [17] J. Marco-Contelles, C.A. Jiménez, Tetrahedron 55, 10511 (1999) http://dx.doi.org/10.1016/S0040-4020(99)00575-X[Crossref]
• [18] B.-Y. Lee, S.R. Park, H.B. Jeon, K.S. Kim, Tetrahedron Lett. 47, 5105 (2006) http://dx.doi.org/10.1016/j.tetlet.2006.05.079[Crossref]
• [19] B.A. Salameh, H. Leffler, U.J. Nilsson, Bioorg. Med. Chem. Lett. 15, 3344 (2005) http://dx.doi.org/10.1016/j.bmcl.2005.05.084[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) http://dx.doi.org/10.1021/jm901265h[Crossref]
• [21] N. Anand, N. Jaiswal, S. Kumar Pandey, A.K. Srivastava, R.P. Tripathi, Carbohydr. Res. 346, 16 (2011) http://dx.doi.org/10.1016/j.carres.2010.10.017[Crossref]
• [22] B.E. Maryanoff, J. Med. Chem. 52, 3431 (2009) http://dx.doi.org/10.1021/jm900141j[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) http://dx.doi.org/10.1021/jm970790w[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) http://dx.doi.org/10.1021/jm0303296[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) http://dx.doi.org/10.1021/jm050063y[Crossref]
• [27] R. Saul, J.P. Chambers, R.J. Molyneux, A.D. Elbein, Arch. Biochem. Biophys. 221, 593 (1983) http://dx.doi.org/10.1016/0003-9861(83)90181-9[Crossref]
• [28] A. Brandi, S. Cicchi, F.M. Cordero, R. Frignoli, A. Goti, S. Picasso, P. Vogel, J. Org. Chem. 60, 6806 (1995) http://dx.doi.org/10.1021/jo00126a033[Crossref]
• [29] V.V. Filichev, E.B. Pedersen, Tetrahedron 57, 9163 (2001) http://dx.doi.org/10.1016/S0040-4020(01)00920-6[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) http://dx.doi.org/10.1021/jo0491096[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.

Identifiers

DOI

10.2478/s11532-012-0002-9