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Volumn 47, Issue 21, 2004, Pages 5224-5229

Carbonic anhydrase inhibitors: The first on-resin screening of a 4-sulfamoylphenylthiourea library

Author keywords

[No Author keywords available]

Indexed keywords

4 ISOTHIOCYANATOBENZENESULFONAMIDE; 4 SULFAMOYLPHENYLTHIOUREA DERIVATIVE; ACETAZOLAMIDE; ANTIGLAUCOMA AGENT; BRINZOLAMIDE; CARBONATE DEHYDRATASE INHIBITOR; DICLOFENAMIDE; DORZOLAMIDE; ETHOXZOLAMIDE; INDISULAM; METHAZOLAMIDE; N [[[4 (AMINOSULFONYL)PHENYL]AMINO]THIOXOMETHYL]ALANINE; N [[[4 (AMINOSULFONYL)PHENYL]AMINO]THIOXOMETHYL]ASPARAGINE; N [[[4 (AMINOSULFONYL)PHENYL]AMINO]THIOXOMETHYL]GLUTAMINE; N [[[4 (AMINOSULFONYL)PHENYL]AMINO]THIOXOMETHYL]ISOLEUCINE; N [[[4 (AMINOSULFONYL)PHENYL]AMINO]THIOXOMETHYL]LEUCINE; N [[[4 (AMINOSULFONYL)PHENYL]AMINO]THIOXOMETHYL]METHIONINE; N [[[4 (AMINOSULFONYL)PHENYL]AMINO]THIOXOMETHYL]PHENYLALANINE; N [[[4 (AMINOSULFONYL)PHENYL]AMINO]THIOXOMETHYL]PROLINE; N [[[4 (AMINOSULFONYL)PHENYL]AMINO]THIOXOMETHYL]TRYPTOPHAN; N [[[4 (AMINOSULFONYL)PHENYL]AMINO]THIOXOMETHYL]VALINE; RESIN; THIOHYDANTOIN DERIVATIVE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

EID: 4744371616     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049692i     Document Type: Article
Times cited : (47)

References (41)
  • 2
    • 0034018870 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors and their therapeutic potential
    • (b) Supuran, C. T.; Scozzafava, A. Carbonic anhydrase inhibitors and their therapeutic potential. Exp. Opin. Ther. Patents 2000, 10, 575-600.
    • (2000) Exp. Opin. Ther. Patents , vol.10 , pp. 575-600
    • Supuran, C.T.1    Scozzafava, A.2
  • 5
    • 0002073966 scopus 로고
    • The links among biochemistry, physiology and pharmacology in carbonic anhydrase mediated systems
    • Botré, F., Gros, G., Storey, B. T., Eds.; VCH: Weinheim, Germany
    • (a) Maren, T. H. The links among biochemistry, physiology and pharmacology in carbonic anhydrase mediated systems. In Carbonic Anhydrase - From Biochemistry and Genetics to Physiology and Clinical Medicine; Botré, F., Gros, G., Storey, B. T., Eds.; VCH: Weinheim, Germany, 1991; pp 186-207.
    • (1991) Carbonic Anhydrase - From Biochemistry and Genetics to Physiology and Clinical Medicine , pp. 186-207
    • Maren, T.H.1
  • 6
    • 0028928792 scopus 로고
    • The development of topical carbonic anhydrase inhibitors
    • (b) Maren, T. H. The development of topical carbonic anhydrase inhibitors. J. Glaucoma 1995, 4, 49-62.
    • (1995) J. Glaucoma , vol.4 , pp. 49-62
    • Maren, T.H.1
  • 7
    • 2442650952 scopus 로고    scopus 로고
    • Clinical applications of carbonic anhydrase inhibitors in ophthalmology
    • Supuran, C. T., Scozzafava, A., Conway J., Eds.; CRC Press: Boca Raton, FL
    • (c) Mincione, F.; Menabuoni, L.; Supuran, C. T. Clinical applications of carbonic anhydrase inhibitors in ophthalmology. In Carbonic anhydrase - Its inhibitors and activators; Supuran, C. T., Scozzafava, A., Conway J., Eds.; CRC Press: Boca Raton, FL, 2004; pp 243-254.
    • (2004) Carbonic Anhydrase - Its Inhibitors and Activators , pp. 243-254
    • Mincione, F.1    Menabuoni, L.2    Supuran, C.T.3
  • 8
    • 0033990833 scopus 로고    scopus 로고
    • Pharmacological and ocular hypotensive properties of topical carbonic anhydrase inhibitors
    • (a) Sugrue, M. F. Pharmacological and ocular hypotensive properties of topical carbonic anhydrase inhibitors. Prog. Retinal Eye Res. 2000, 19, 87-112.
    • (2000) Prog. Retinal Eye Res. , vol.19 , pp. 87-112
    • Sugrue, M.F.1
  • 9
    • 0034014371 scopus 로고    scopus 로고
    • Dose-response evaluation of the ocular hypotensive effect of brinzolamide ophthalmic suspension (Azopt)
    • Brinzolamide dose-response study group
    • (b) Silver, L. H. Dose-response evaluation of the ocular hypotensive effect of brinzolamide ophthalmic suspension (Azopt). Brinzolamide dose-response study group. Surv. Ophthalmol. 2000, 44 (Suppl. 2), 147-153.
    • (2000) Surv. Ophthalmol. , vol.44 , Issue.2 SUPPL. , pp. 147-153
    • Silver, L.H.1
  • 10
    • 0033765660 scopus 로고    scopus 로고
    • Novel sulphonamide derivatives for the treatment of cancer
    • (a) Owa, T.; Nagasu, T. Novel sulphonamide derivatives for the treatment of cancer. Exp. Opin. Ther. Patents 2000, 10, 1725-1740.
    • (2000) Exp. Opin. Ther. Patents , vol.10 , pp. 1725-1740
    • Owa, T.1    Nagasu, T.2
  • 12
    • 0037315480 scopus 로고    scopus 로고
    • Indisulam - An anticancer sulfonamide in clinical development
    • (c) Supuran, C. T. Indisulam - an anticancer sulfonamide in clinical development. Exp. Opin. Invest. Drugs 2003, 12, 283-287.
    • (2003) Exp. Opin. Invest. Drugs , vol.12 , pp. 283-287
    • Supuran, C.T.1
  • 13
    • 0348147633 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Indisulam (E7070) is a potent inhibitor of cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX
    • (d) Abbate, F.; Casini, A.; Owa, T.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: Indisulam (E7070) is a potent inhibitor of cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorg. Med. Chem. Lett. 2004, 14, 217-223.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 217-223
    • Abbate, F.1    Casini, A.2    Owa, T.3    Scozzafava, A.4    Supuran, C.T.5
  • 16
    • 0033566151 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Synthesis of water-soluble, topically effective, intraocular pressure-lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: Is the tail more important than the ring?
    • (a) Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C. T. Carbonic anhydrase inhibitors: Synthesis of water-soluble, topically effective, intraocular pressure-lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: is the tail more important than the ring? J. Med. Chem. 1999, 42, 2641-2650.
    • (1999) J. Med. Chem. , vol.42 , pp. 2641-2650
    • Scozzafava, A.1    Menabuoni, L.2    Mincione, F.3    Briganti, F.4    Mincione, G.5    Supuran, C.T.6
  • 17
    • 0033539043 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Synthesis of water-soluble, amino acyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route
    • (b) Scozzafava, A.; Briganti, F.; Mincione, G.; Menabuoni, L.; Mincione, F.; Supuran, C. T. Carbonic anhydrase inhibitors: Synthesis of water-soluble, amino acyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route. J. Med. Chem. 1999, 42, 3690-3700.
    • (1999) J. Med. Chem. , vol.42 , pp. 3690-3700
    • Scozzafava, A.1    Briganti, F.2    Mincione, G.3    Menabuoni, L.4    Mincione, F.5    Supuran, C.T.6
  • 18
    • 0033490798 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Synthesis of water-soluble, topically effective intraocular pressure lowering aromatic/heterocyclic sulfonamides containing 8-quinoline-sulfonyl moieties: Is the tail more important than the ring?
    • (a) Borras, J.; Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C. T. Carbonic anhydrase inhibitors: Synthesis of water-soluble, topically effective intraocular pressure lowering aromatic/heterocyclic sulfonamides containing 8-quinoline-sulfonyl moieties: is the tail more important than the ring? Bioorg. Med. Chem. 1999, 7, 2397-2406.
    • (1999) Bioorg. Med. Chem. , vol.7 , pp. 2397-2406
    • Borras, J.1    Scozzafava, A.2    Menabuoni, L.3    Mincione, F.4    Briganti, F.5    Mincione, G.6    Supuran, C.T.7
  • 19
    • 0034599954 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Topical sulfonamide antiglaucoma agents incorporating secondary amine moieties
    • (b) Renzi, G.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: Topical sulfonamide antiglaucoma agents incorporating secondary amine moieties. Bioorg. Med. Chem. Lett. 2000, 10, 673-676.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 673-676
    • Renzi, G.1    Scozzafava, A.2    Supuran, C.T.3
  • 20
    • 0033866735 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Sulfonamides incorporating furan-, thiophene- and pyrrole-carboxamido groups possess strong topical intraocular pressure lowering properties as aqueous suspensions
    • (c) Ilies, M.; Supuran, C. T.; Scozzafava, A.; Casini, A.; Mincione, F.; Menabuoni, L.; Caproiu, M. T.; Maganu, M.; Banciu, M. D. Carbonic anhydrase inhibitors. Sulfonamides incorporating furan-, thiophene- and pyrrole-carboxamido groups possess strong topical intraocular pressure lowering properties as aqueous suspensions. Bioorg. Med. Chem. 2000, 8, 2145-2155.
    • (2000) Bioorg. Med. Chem. , vol.8 , pp. 2145-2155
    • Ilies, M.1    Supuran, C.T.2    Scozzafava, A.3    Casini, A.4    Mincione, F.5    Menabuoni, L.6    Caproiu, M.T.7    Maganu, M.8    Banciu, M.D.9
  • 21
    • 0034078164 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Part 78. Synthesis of water-soluble sulfonamides incorporating xe2-alanyl moieties, possessing long-lasting intraocular pressure lowering properties via the topical route
    • (a) Supuran, C. T.; Briganti, F.; Menabuoni, L.; Mincione, G.; Mincione, F.; Scozzafava, A. Carbonic anhydrase inhibitors. Part 78. Synthesis of water-soluble sulfonamides incorporating xe2-alanyl moieties, possessing long-lasting intraocular pressure lowering properties via the topical route. Eur. J. Med. Chem. 2000, 35, 309-321.
    • (2000) Eur. J. Med. Chem. , vol.35 , pp. 309-321
    • Supuran, C.T.1    Briganti, F.2    Menabuoni, L.3    Mincione, G.4    Mincione, F.5    Scozzafava, A.6
  • 22
    • 0033452938 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Part 79. Synthesis and ocular pharmacology of topically acting sulfonamides incorporating GABA moieties in their molecule, with long-lasting intraocular pressure lowering properties
    • (b) Mincione, G.; Menabuoni, L.; Briganti, F.; Mincione, F.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Part 79. Synthesis and ocular pharmacology of topically acting sulfonamides incorporating GABA moieties in their molecule, with long-lasting intraocular pressure lowering properties. Eur. J. Pharm. Sci. 1999, 9, 185-199.
    • (1999) Eur. J. Pharm. Sci. , vol.9 , pp. 185-199
    • Mincione, G.1    Menabuoni, L.2    Briganti, F.3    Mincione, F.4    Scozzafava, A.5    Supuran, C.T.6
  • 24
    • 0034649604 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Water-soluble 4-sulfamoylphenylthioureas as topical intraocular pressure-lowering agents with long-lasting effects
    • Casini, A.; Scozzafava, A.; Mincione, F.; Menabuoni, L.; Ilies, M. A.; Supuran, C. T. Carbonic anhydrase inhibitors: Water-soluble 4- sulfamoylphenylthioureas as topical intraocular pressure-lowering agents with long-lasting effects. J. Med. Chem. 2000, 43, 4884-4892.
    • (2000) J. Med. Chem. , vol.43 , pp. 4884-4892
    • Casini, A.1    Scozzafava, A.2    Mincione, F.3    Menabuoni, L.4    Ilies, M.A.5    Supuran, C.T.6
  • 25
    • 0001550946 scopus 로고
    • p-Substituted phenyl isothiocyanates and some related thioureas
    • McKee, R. L.; Bost, R. W. p-Substituted phenyl isothiocyanates and some related thioureas. J. Am. Chem. Soc. 1946, 68, 2506-2507.
    • (1946) J. Am. Chem. Soc. , vol.68 , pp. 2506-2507
    • McKee, R.L.1    Bost, R.W.2
  • 26
    • 0014772602 scopus 로고
    • Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides
    • Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970, 34, 595-598.
    • (1970) Anal. Biochem. , vol.34 , pp. 595-598
    • Kaiser, E.1    Colescott, R.L.2    Bossinger, C.D.3    Cook, P.I.4
  • 27
    • 0001433809 scopus 로고
    • Method for determination of the amino acid sequence in peptides
    • (a) Edman, P. Method for determination of the amino acid sequence in peptides. Acta Chem. Scand. 1950, 4, 283-293.
    • (1950) Acta Chem. Scand. , vol.4 , pp. 283-293
    • Edman, P.1
  • 28
    • 0014064044 scopus 로고
    • A protein sequenator
    • (b) Edman, P.; Begg, G. A protein sequenator. Eur. J. Biochem. 1967, 1, 80-91.
    • (1967) Eur. J. Biochem. , vol.1 , pp. 80-91
    • Edman, P.1    Begg, G.2
  • 29
    • 0015219574 scopus 로고
    • Solid-phase Edman degradation. An automatic peptide sequencer
    • Laursen, R. A. Solid-phase Edman degradation. An automatic peptide sequencer. Eur. J. Biochem. 1971, 20, 89-102.
    • (1971) Eur. J. Biochem. , vol.20 , pp. 89-102
    • Laursen, R.A.1
  • 30
    • 84958239785 scopus 로고    scopus 로고
    • Combinatorial library based on the one-bead-one-compound concept
    • Jung, G., Ed.; VCH: Weinheim, Germany
    • Lam, K. S.; Lebl M. Combinatorial library based on the one-bead-one-compound concept. In Combinatorial peptide and nonpeptide libraries; Jung, G., Ed.; VCH: Weinheim, Germany, 1996; pp 173-201.
    • (1996) Combinatorial Peptide and Nonpeptide Libraries , pp. 173-201
    • Lam, K.S.1    Lebl, M.2
  • 31
    • 0014062860 scopus 로고
    • The catalytic versatility of erythrocyte carbonic anhydrase. III. Kinetic studies of the enzyme-catalyzed hydrolysis of p-nitrophenyl acetate
    • Pocker, Y.; Stone, J. T. The catalytic versatility of erythrocyte carbonic anhydrase. III. Kinetic studies of the enzyme-catalyzed hydrolysis of p-nitrophenyl acetate. Biochemistry 1967, 6, 668-678.
    • (1967) Biochemistry , vol.6 , pp. 668-678
    • Pocker, Y.1    Stone, J.T.2
  • 33
    • 0025354634 scopus 로고
    • Fine tuning of the catalytic properties of carbonic anhydrase. Studies of a Thr200-His variant of human isoenzyme II
    • Behravan, G., Jonsson, B. H., Lindskog, S. Fine tuning of the catalytic properties of carbonic anhydrase. Studies of a Thr200-His variant of human isoenzyme II. Eur. J. Biochem. 1990, 190, 351-357.
    • (1990) Eur. J. Biochem. , vol.190 , pp. 351-357
    • Behravan, G.1    Jonsson, B.H.2    Lindskog, S.3
  • 34
    • 0017378545 scopus 로고
    • Carbon-13 nuclear magnetic resonance probe of active site ionization of human carbonic anhydrase B
    • Khalifah, R. G.; Strader, D. J.; Bryant, S. H.; Gibson, S. M. Carbon-13 nuclear magnetic resonance probe of active site ionization of human carbonic anhydrase B. Biochemistry 1977, 16, 2241-2247.
    • (1977) Biochemistry , vol.16 , pp. 2241-2247
    • Khalifah, R.G.1    Strader, D.J.2    Bryant, S.H.3    Gibson, S.M.4
  • 36
    • 0016722749 scopus 로고
    • The catalytic mechanism of carbonic anhydrase. Hydrogen-isotope effects on the kinetic parameters of the human C isoenzyme
    • Steiner, H.; Jonsson, B. H.; Lindskog, S. The catalytic mechanism of carbonic anhydrase. Hydrogen-isotope effects on the kinetic parameters of the human C isoenzyme. Eur. J. Biochem. 1975, 59, 253-259.
    • (1975) Eur. J. Biochem. , vol.59 , pp. 253-259
    • Steiner, H.1    Jonsson, B.H.2    Lindskog, S.3
  • 37
    • 1242318777 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides
    • Vullo, D.; Franchi, M.; Gallori. E.; Antel, J.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J. Med. Chem. 2004, 47, 1272-1279.
    • (2004) J. Med. Chem. , vol.47 , pp. 1272-1279
    • Vullo, D.1    Franchi, M.2    Gallori, E.3    Antel, J.4    Scozzafava, A.5    Supuran, C.T.6
  • 38
    • 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
    • (a) 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
  • 39
    • 0344981308 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Inhibition of transmembrane, tumor-associated isozyme IX, and cytosolic isozymes I and II with aliphatic sulfamates
    • (b) 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
  • 40
    • 0842281270 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: The first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX
    • (c) 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
  • 41
    • 1842628633 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX
    • (d) 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


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