Sulfonamidoglycosylation of methyl glycosides employing perchloric acid supported on silica gel

Journal of Carbohydrate Chemistry

Volumn 27, Issue 3, 2008, Pages 141-147

  Colinas, Pedro A ^a   Núñez, Nicolás A ^a   Bravo, Rodolfo D ^a  

^a UNIVERSIDAD NACIONAL DE LA PLATA   (Argentina)

Author keywords

Methyl glycosides; Perchloric acid silica; Sulfonamidoglycosylation

Indexed keywords

EID: 45949093914     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300802030829     Document Type: Article

References (15)

1. Scozzafava, A.; Owa, T.; Mastrolorenzo, A.; Supuran, C.T. Anticancer and antiviral sulfonamides. Curr. Med. Chem. 2003, 10, 925-953.
2. Supuran, C.T. Indisulam: an anticancer sulfonamide in clinical development. Exp. Opin. Invest. Drugs 2003, 12, 283-287.
3. Jordan, M.A.; Wilson, L. Microtubules as a target for anticancer drugs. Nat. Rev. Cancer 2004, 4, 253-265.
4. Medina, J.C.; Roche, D.; Shan, B.; Learned, M.; Frankmoelle, W.P.; Clark, D.L.; Rosen, T.; Jaen, J.C. Novel halogenated sulfonamides inhibit the growth of multidrug resistant MCF-7/ADR cancer cells. Bioorg. Med. Chem. Lett. 1999, 9, 1843-1846.
5. Shan, B.; Medina, J.C.; Santha, E.; Frankmoelle, W.P.; Chou, T.-C.; Narbut, M.R.; Stott, D.; Wu, P.; Jaen, J.C.; Rosen, T.; Timmermans, P.B.M.W.M.; Beckmann, H. Selective, covalent modification of beta-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc. Natl. Acad. Sci. USA 1999, 96, 5686-5691.
6. Abbate, F.; Casini, A.; Owa, t.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorg. Med. Chem. Lett. 2004, 14, 217-223.
7. Robertson, N.; Potter, C.; Harris, A.L. Role of carbonic anhydrase IX in human tumor cell growth, survival, and invasion. Cancer Res. 2004, 64, 6160-6165.
8. Griffith, D.A.; Danishefsky, S.J. Sulfonamidoglycosylation of glycals. A route to oligosaccharides with 2-aminohexose subunits. J. Am. Chem. Soc. 1990, 112, 5811-5819.
9. For a review see; Danishefsky, S.J.; Bilodeau, M.T. Glycals in organic synthesis: the evolution of comprehensive strategies for the assembly of oligosaccharides and glycoconjugates of biological consequence. Angew. Chem. Int. Ed. Engl. 1996, 35, 1380-1419.
10. Colinas, P.A.; Bravo, R.D. A novel sulfonamidoglycosylation of glycals. Org. Lett. 2003, 5, 4509-4511.
11. Colinas, P.A.; Bravo, R.D. Sulfonamidoglycosylation of methyl ribofuranosides: a novel approach to furanosylsulfonamides. Tetrahedron Lett. 2005, 46, 1687-1689.
12. Corma, A.; García, H. Lewis Acids: From conventional homogeneous to green homogeneous and heterogeneous catalysis. Chem. Rev. 2003, 103, 4307-4365.
13. Chakraborti, A.K.; Gulhane, R. Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines. Chem. Commun. 2003, 1896-1897.
14. For applications of this reagent system see: Narasimhulu, M.; Reddy, T.S.; Mahesh, K.C.; Prabhakar, P.; Rao, Ch.B.; Venkateswarlu, Y. Silica supported perchloric acid: A mild and highly efficient heterogeneous catalyst for the synthesis of poly-substituted quinolines via Friedländer hetero-annulation. J. Mol. Catal. A Chem. 2007, 266, 114-117 and references therein.
15. Colinas, P.A.; Bravo, R.D.; Vullo, D.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors. Inhibition of cytosolic isoforms I and II, and extracellular isoforms IV, IX, and XII with sulfamides incorporating sugar moieties. Bioorg. Med. Chem. Lett. 2007, 17, 5086-5090.