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Volumn 49, Issue 22, 2006, Pages 6539-6548

A novel class of carbonic anhydrase inhibitors: Glycoconjugate benzene sulfonamides prepared by "click-tailing"

Author keywords

[No Author keywords available]

Indexed keywords

ACETAZOLAMIDE; BENZENESULFONAMIDE DERIVATIVE; BRINZOLAMIDE; CARBOHYDRATE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; DICLOFENAMIDE; ETHOXZOLAMIDE; GLYCOCONJUGATE; INDISULAM; ISOENZYME; METHAZOLAMIDE; PACLITAXEL; TRIAZOLE;

EID: 33750471952     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060967z     Document Type: Article
Times cited : (168)

References (30)
  • 1
    • 2442579987 scopus 로고    scopus 로고
    • Carbonic anhydrases: Catalytic and inhibition mechanism, distribution and physiological roles
    • Supuran, C. T., Scozzafava, A., Conway, J., Eds.: CRC Press: Boca Raton, FL
    • Supuran, C. T. Carbonic anhydrases: Catalytic and inhibition mechanism, distribution and physiological roles. In Carbonic Anhydrase: Its Inhibitors and Activators; Supuran, C. T., Scozzafava, A., Conway, J., Eds.: CRC Press: Boca Raton, FL, 2004: pp 1-24.
    • (2004) Carbonic Anhydrase: Its Inhibitors and Activators , pp. 1-24
    • Supuran, C.T.1
  • 4
    • 3442883664 scopus 로고    scopus 로고
    • Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects
    • Pastorekova, S.; Parkkila, S.; Pastorek, J.; Supuran, C. T. Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects. J. Enzymol. Inhib. Med. Chem. 2004, 19, 199-229.
    • (2004) J. Enzymol. Inhib. Med. Chem. , vol.19 , pp. 199-229
    • Pastorekova, S.1    Parkkila, S.2    Pastorek, J.3    Supuran, C.T.4
  • 6
    • 0842281270 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX
    • Pastorekova, S.; Casini, A.; Scozzafava, A.; Vullo, D.; Pastorek, J.; Supuran, C. T. Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX. Bioorg. Med. Chem. Lett. 2004, 14, 869-873.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 869-873
    • Pastorekova, S.1    Casini, A.2    Scozzafava, A.3    Vullo, D.4    Pastorek, J.5    Supuran, C.T.6
  • 7
    • 4544388351 scopus 로고    scopus 로고
    • Cancer-related carbonic anhydrase isozymes
    • Supuran, C. T., Scozzafava, A., Conway, J., Eds.; CRC Press: Boca Raton, FL
    • Pastorekova, S.; Pastorek, J. Cancer-related carbonic anhydrase isozymes. In Carbonic Anhydrase-Its Inhibitors and Activators; Supuran, C. T., Scozzafava, A., Conway, J., Eds.; CRC Press: Boca Raton, FL, 2004; pp 253-280.
    • (2004) Carbonic Anhydrase - Its Inhibitors and Activators , pp. 253-280
    • Pastorekova, S.1    Pastorek, J.2
  • 9
    • 0035289779 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Del. Rev. 2001, 46, 3-26.
    • (2001) Adv. Drug Del. Rev. , vol.46 , pp. 3-26
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 10
    • 0041703019 scopus 로고    scopus 로고
    • Pharmacological effects of formulation vehicles. Implications for cancer chemotherapy
    • ten Tije, A. J.; Verweij, J.; Loos, W. J.; Sparreboom, A. Pharmacological effects of formulation vehicles. Implications for cancer chemotherapy. Clin. Pharmacokinet. 2003, 42, 665-685.
    • (2003) Clin. Pharmacokinet. , vol.42 , pp. 665-685
    • Ten Tije, A.J.1    Verweij, J.2    Loos, W.J.3    Sparreboom, A.4
  • 11
    • 32944482677 scopus 로고    scopus 로고
    • Phase III trial of nanoparticle albumin-bound paclitaxel compared with polyethylated castor oil-based paclitaxel in women with breast cancer
    • Gradishar, W. J.; Tjulandin, S.; Davidson, N.; Shaw, H.; Desai, N.; Bhar, P.; Hawkins, M.; O'Shaughnessy, J. Phase III trial of nanoparticle albumin-bound paclitaxel compared with polyethylated castor oil-based paclitaxel in women with breast cancer. J. Clin. Oncol. 2005, 23, 7794-7803.
    • (2005) J. Clin. Oncol. , vol.23 , pp. 7794-7803
    • Gradishar, W.J.1    Tjulandin, S.2    Davidson, N.3    Shaw, H.4    Desai, N.5    Bhar, P.6    Hawkins, M.7    O'Shaughnessy, J.8
  • 12
    • 4444244953 scopus 로고    scopus 로고
    • Lipid, sugar and liposaccharide based delivery systems 2
    • Blanchfield, J.; Toth, I. Lipid, sugar and liposaccharide based delivery systems 2. Curr. Med. Chem. 2004, 11, 2375-2382.
    • (2004) Curr. Med. Chem. , vol.11 , pp. 2375-2382
    • Blanchfield, J.1    Toth, I.2
  • 13
    • 0642346843 scopus 로고    scopus 로고
    • Aspects of the stability and bioavailability of carbohydrates and carbohydrate derivatives
    • Drinnan, N. B.; Vari, F. Aspects of the stability and bioavailability of carbohydrates and carbohydrate derivatives. Mini Rev. Med. Chem. 2003, 3, 633-649.
    • (2003) Mini Rev. Med. Chem. , vol.3 , pp. 633-649
    • Drinnan, N.B.1    Vari, F.2
  • 14
    • 0345255892 scopus 로고    scopus 로고
    • Recent developments in the synthesis and discovery of oligosaccharides and glycoconjugates for the treatment of disease
    • Macmillan, D.; Daines, A. M. Recent developments in the synthesis and discovery of oligosaccharides and glycoconjugates for the treatment of disease. Curr. Med. Chem. 2003, 10, 2733-2773.
    • (2003) Curr. Med. Chem. , vol.10 , pp. 2733-2773
    • Macmillan, D.1    Daines, A.M.2
  • 15
    • 85037397162 scopus 로고
    • Iodine catalyzed Ferrier reaction 1. A mild and highly versatile glycosylation of hydroxy and phenolic groups
    • Koreeda, M.; Houston, T. A.; Shull, B. K.; Klemke, E.; Tuinman, R. J. Iodine catalyzed Ferrier reaction 1. A mild and highly versatile glycosylation of hydroxy and phenolic groups. Synlett. 1995, 90-92.
    • (1995) Synlett. , pp. 90-92
    • Koreeda, M.1    Houston, T.A.2    Shull, B.K.3    Klemke, E.4    Tuinman, R.J.5
  • 16
    • 18044400960 scopus 로고    scopus 로고
    • Service, R. F. Science 2001, 291, 2342-2342.
    • (2001) Science , vol.291 , pp. 2342-2342
    • Service, R.F.1
  • 17
    • 0347517808 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: N-(p-Sulfamoylphenyl)-α-n- glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits
    • Winum, J.-V.; Casini, A.; Mincione, F.; Starnotti, M.; Montero, J.-L.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: N-(p-Sulfamoylphenyl)-α-n-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits. Bioorg. Med. Chem. Lett. 2004, 14, 225-229.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 225-229
    • Winum, J.-V.1    Casini, A.2    Mincione, F.3    Starnotti, M.4    Montero, J.-L.5    Scozzafava, A.6    Supuran, C.T.7
  • 18
    • 33745727392 scopus 로고    scopus 로고
    • Synthetic utility of glycosyl triazoles in carbohydrate chemistry
    • Wilkinson, B. L.; Bornaghi, L. F.; Poulsen, S.-A.; Houston, T. A. Synthetic utility of glycosyl triazoles in carbohydrate chemistry. Tetrahedron 2006, 62, 8115-8125.
    • (2006) Tetrahedron , vol.62 , pp. 8115-8125
    • Wilkinson, B.L.1    Bornaghi, L.F.2    Poulsen, S.-A.3    Houston, T.A.4
  • 19
    • 0035833062 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: 4-Sulfamoyl-benzenecarboxamides and 4-chloro-3-sulfamoyl-benzenecarboxamides with strong topical antiglaucoma properties
    • Mincione, F.; Starnotti, M.; Menabuoni, L.; Scozzafava, A.; Casini, A.; Supuran, C. T. Carbonic anhydrase inhibitors: 4-Sulfamoyl-benzenecarboxamides and 4-chloro-3-sulfamoyl-benzenecarboxamides with strong topical antiglaucoma properties. Bioorg. Med. Chem. Lett. 2001, 11, 1787-1791.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 1787-1791
    • Mincione, F.1    Starnotti, M.2    Menabuoni, L.3    Scozzafava, A.4    Casini, A.5    Supuran, C.T.6
  • 20
    • 84985560323 scopus 로고
    • Construction of disaccharide N-glyco-peptides-Synthesis of the linkage region of the transmembrane-neuraminidase of an influenza virus
    • Kunz, H.; Waldmann, H. Construction of disaccharide N-glyco-peptides- Synthesis of the linkage region of the transmembrane-neuraminidase of an influenza virus. Angew. Chem., Int. Ed. Engl. 1985, 24, 883-885.
    • (1985) Angew. Chem., Int. Ed. Engl. , vol.24 , pp. 883-885
    • Kunz, H.1    Waldmann, H.2
  • 21
    • 0027906299 scopus 로고
    • An imino-linked carba-disaccharide α-D-mannosidase inhibitor
    • Cottaz, S.; Brimacombe, J. S.; Ferguson, M. A. J. An imino-linked carba-disaccharide α-D-mannosidase inhibitor. Carbohydr. Res. 1993, 247, 341-345.
    • (1993) Carbohydr. Res. , vol.247 , pp. 341-345
    • Cottaz, S.1    Brimacombe, J.S.2    Ferguson, M.A.J.3
  • 22
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 23
    • 0015239422 scopus 로고
    • The carbon dioxide hydration activity of carbonic anhydrase
    • Khalifah, R. G. The carbon dioxide hydration activity of carbonic anhydrase. J. Biol Chem. 1971, 246, 2561-2573.
    • (1971) J. Biol Chem. , vol.246 , pp. 2561-2573
    • Khalifah, R.G.1
  • 24
    • 0344981308 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Inhibition of transmembrane, tumor-associated isozyme IX, and cytosolic isozymes I and II with aliphatic sulfamates
    • Winum, J.-Y.; Vullo, D.; Casini, A.; Montero, J.-L.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: Inhibition of transmembrane, tumor-associated isozyme IX, and cytosolic isozymes I and II with aliphatic sulfamates. J. Med. Chem. 2003, 46, 5471-5477.
    • (2003) J. Med. Chem. , vol.46 , pp. 5471-5477
    • Winum, J.-Y.1    Vullo, D.2    Casini, A.3    Montero, J.-L.4    Scozzafava, A.5    Supuran, C.T.6
  • 26
    • 0038587356 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes I and II and transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors
    • Winum, J.-Y.; Vullo, D.; Casini, A.; Montero, J.-L.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes I and II and transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors. J. Med. Chem. 2003, 46, 2197-2204.
    • (2003) J. Med. Chem. , vol.46 , pp. 2197-2204
    • Winum, J.-Y.1    Vullo, D.2    Casini, A.3    Montero, J.-L.4    Scozzafava, A.5    Supuran, C.T.6
  • 27
    • 22744446294 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Sulfonamides inhibit isozyme IX mediated acidification of hypoxic tumors. Fluorescent sulfonamides design as probes of membrane-bound carbonic anhydrase isozymes involvement in tumorigenesis
    • Cecchi, A.; Hulikova, A.; Pastorek, J.; Pastorekova, S.; Scozzafava, A.; Winum, J.-Y.; Montero, J.-L.; Supuran, C. T. Carbonic anhydrase inhibitors. Sulfonamides inhibit isozyme IX mediated acidification of hypoxic tumors. Fluorescent sulfonamides design as probes of membrane-bound carbonic anhydrase isozymes involvement in tumorigenesis. J. Med. Chem. 2005, 48, 4834-484.
    • (2005) J. Med. Chem. , vol.48 , pp. 4834-5484
    • Cecchi, A.1    Hulikova, A.2    Pastorek, J.3    Pastorekova, S.4    Scozzafava, A.5    Winum, J.-Y.6    Montero, J.-L.7    Supuran, C.T.8
  • 28
    • 1842628633 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX
    • Casey, J. R.; Morgan, P. E.; Vullo, D.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX. J. Med. Chem. 2004, 47, 2337-2347.
    • (2004) J. Med. Chem. , vol.47 , pp. 2337-2347
    • Casey, J.R.1    Morgan, P.E.2    Vullo, D.3    Scozzafava, A.4    Mastrolorenzo, A.5    Supuran, C.T.6
  • 29
    • 0034823319 scopus 로고    scopus 로고
    • Chemoselective approaches to glycoprotein assembly
    • Hang, H. C.; Bertozzi, C. R. Chemoselective approaches to glycoprotein assembly. Acc. Chem. Res. 2001, 34, 727-736.
    • (2001) Acc. Chem. Res. , vol.34 , pp. 727-736
    • Hang, H.C.1    Bertozzi, C.R.2
  • 30
    • 0037463790 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides
    • Vullo, D.; Franchi, M.; Gallori, E.; Pastorek, J.; Scozzafava, A.; Pastorekova, S.; Supuran, C. T. Carbonic anhydrase inhibitors. Inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides. Bioorg. Med. Chem. Lett. 2003, 13, 1005-1009.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 1005-1009
    • Vullo, D.1    Franchi, M.2    Gallori, E.3    Pastorek, J.4    Scozzafava, A.5    Pastorekova, S.6    Supuran, C.T.7


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