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Volumn 30, Issue 5, 2015, Pages 737-745

Fluorinated pyrrolidines and piperidines incorporating tertiary benzenesulfonamide moieties are selective carbonic anhydrase II inhibitors

Author keywords

Carbonic anhydrase; fluorine; selectivity; superacid; tertiary benzenesulfonamides

Indexed keywords

1 (4 AMINOBENZENESULFONYL) 2 (FLUOROETHYL)PYRROLIDINE; 1 (4 AMINOBENZENESULFONYL) 2 ETHYLPYRROLIDINE; 1 (4 AMINOBENZENESULFONYL) 2 VINYLPYRROLIDINE; 1 (4 NOSYL) 1,2,5,6 TETRAHYDROPYRIDINE; 1 (4 NOSYL) 2 (2 CHLOROFLUOROETHYL)PYRROLIDINE; 1 (4 NOSYL) 2 (CHLORO 2 FLUOROETHYL)PYRROLIDINE; 1 (4 NOSYL) 2 (FLUOROETHYL)PYRROLIDINE; 1 (4 NOSYL) 2 VINYLPYRROLIDINE; 1 (4 NOSYL) 4 CHLORO 3 FLUOROPIPERIDINE; 1 (4 NOSYL) 4 METHANESULFONATEPIPERIDINE; 1 (4 NOSYL)PIPERIDINE 4 OL; 1 (4 NOSYL)PYRROLIDINE 2 CARBALDEHYDE; BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE XII; METHYL 1 (4 NOSYL)PYRROLIDINE 2 CARBOXYLATE; N (4 NOSYL) 3 CHLORO 4 FLUOROPIPERIDINE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG; BENZENESULFONAMIDE; SULFONAMIDE;

EID: 84940757919     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2014.963072     Document Type: Article
Times cited : (34)

References (57)
  • 1
    • 42149143745 scopus 로고    scopus 로고
    • Carbonic anhydrase as a model for biophysical and physical-organic studies of proteins and protein-ligand binding
    • Krishnamurthy VM, Kaufman GK, Urbach, AR, et al. Carbonic anhydrase as a model for biophysical and physical-organic studies of proteins and protein-ligand binding. Chem Rev 2008;108:946-1051.
    • (2008) Chem Rev , vol.108 , pp. 946-1051
    • Krishnamurthy, V.M.1    Kaufman, G.K.2    Urbach, A.R.3
  • 2
    • 79961070760 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors and activators for novel therapeutic applications
    • Supuran CT. Carbonic anhydrase inhibitors and activators for novel therapeutic applications. Future Med Chem 2011;3:1165-80.
    • (2011) Future Med Chem , vol.3 , pp. 1165-1180
    • Supuran, C.T.1
  • 4
    • 38849143765 scopus 로고    scopus 로고
    • Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators
    • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discovery 2008;7:168-81.
    • (2008) Nat Rev Drug Discovery , vol.7 , pp. 168-181
    • Supuran, C.T.1
  • 5
    • 42549148009 scopus 로고    scopus 로고
    • Carbonic anhydrase IX: A new druggable target for the design of antitumor agents
    • Winum JY, Rami M, Scozzafava A, et al. Carbonic anhydrase IX: a new druggable target for the design of antitumor agents. Med Res Rev 2008;28:445-63.
    • (2008) Med Res Rev , vol.28 , pp. 445-463
    • Winum, J.Y.1    Rami, M.2    Scozzafava, A.3
  • 7
    • 84939133284 scopus 로고    scopus 로고
    • Recent advances in the discovery of zinc-binding motifs for the development of carbonic anhydrase inhibitors
    • Winum JY, Supuran CT. Recent advances in the discovery of zinc-binding motifs for the development of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2014;18:1-4.
    • (2014) J Enzyme Inhib Med Chem , vol.18 , pp. 1-4
    • Winum, J.Y.1    Supuran, C.T.2
  • 8
    • 5144224910 scopus 로고    scopus 로고
    • Development of sulfonamide carbonic anhydrase inhibitors
    • Supuran CT, Scozzafava A, Conway J, eds. Boca Raton (FL): CRC Press
    • Supuran CT, Casini A, Scozzafava A. Development of sulfonamide carbonic anhydrase inhibitors. In: Supuran CT, Scozzafava A, Conway J, eds. Carbonic anhydrase: its inhibitors and activators. Boca Raton (FL): CRC Press; 2004:67-147.
    • (2004) Carbonic Anhydrase: Its Inhibitors and Activators. , pp. 67-147
    • Supuran, C.T.1    Casini, A.2    Scozzafava, A.3
  • 9
    • 0037675804 scopus 로고    scopus 로고
    • Zinc complexes of benzothiazole-derived Schiff bases with antibacterial activity
    • Chohan ZH, Scozzafava A, Supuran CT. Zinc complexes of benzothiazole-derived Schiff bases with antibacterial activity. J Enzyme Inhib Med Chem 2003;18:259-63.
    • (2003) J Enzyme Inhib Med Chem , vol.18 , pp. 259-263
    • Chohan, Z.H.1    Scozzafava, A.2    Supuran, C.T.3
  • 10
    • 84865850354 scopus 로고    scopus 로고
    • Structure-bases drug discovery of carbonic anhydrase inhibitors
    • Supuran CT. Structure-bases drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:759-72.
    • (2012) J Enzyme Inhib Med Chem , vol.27 , pp. 759-772
    • Supuran, C.T.1
  • 11
    • 84878041301 scopus 로고    scopus 로고
    • Anti-infective carbonic anhydrase inhibitors: A patent and literature review
    • Capasso C, Supuran CT. Anti-infective carbonic anhydrase inhibitors: a patent and literature review. Expert Opin Ther Pat 2013;23: 693-704.
    • (2013) Expert Opin Ther Pat , vol.23 , pp. 693-704
    • Capasso, C.1    Supuran, C.T.2
  • 12
    • 84899088472 scopus 로고    scopus 로고
    • Safety of carbonic anhydrase inhibitors
    • Swenson ER. Safety of carbonic anhydrase inhibitors. Expert Opin Drug Saf 2014;13:459-72.
    • (2014) Expert Opin Drug Saf , vol.13 , pp. 459-472
    • Swenson, E.R.1
  • 13
    • 0031776867 scopus 로고    scopus 로고
    • Metal complexes of heterocyclic sulfonamides: A new class of strong topical intraocular pressure-lowering agents with potential use as antiglaucoma drugs
    • Supuran CT, Mincione F, Scozzafava A, et al. Metal complexes of heterocyclic sulfonamides: a new class of strong topical intraocular pressure-lowering agents with potential use as antiglaucoma drugs. Eur J Med Chem 1998;33:247-54.
    • (1998) Eur J Med Chem , vol.33 , pp. 247-254
    • Supuran, C.T.1    Mincione, F.2    Scozzafava, A.3
  • 14
    • 84863501358 scopus 로고    scopus 로고
    • Multiple binding modes of inhibitors to carbonic anhydrases: How to design specific drugs targeting 15 different isoforms?
    • Alterio V, Di Fiore A, D'Ambrosio K, Supuran CT. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem Rev 2012; 112:4421-68.
    • (2012) Chem Rev , vol.112 , pp. 4421-4468
    • Alterio, V.1    Di Fiore, A.2    D'Ambrosio, K.3    Supuran, C.T.4
  • 15
    • 34147144592 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Inhibition of isozymes I, II and IX with triazole-linked O-glycosides of benzene sulfonamides
    • Wilkinson BL, Bornaghi LF, Houston TA, et al. Carbonic anhydrase inhibitors: inhibition of isozymes I, II and IX with triazole-linked O-glycosides of benzene sulfonamides. J Med Chem 2007;50: 1651-7.
    • (2007) J Med Chem , vol.50 , pp. 1651-1657
    • Wilkinson, B.L.1    Bornaghi, L.F.2    Houston, T.A.3
  • 16
    • 0036700515 scopus 로고    scopus 로고
    • Unsymmetrical 1,1' - Disubstituted ferrocenes: Synthesis of Co(ii), Cu(ii), Ni(ii) and Zn(ii) chelates of ferrocenyl-1-thiadiazolo-1' -tetrazole, -1-thiadiazolo-1' - Triazole and -1-tetrazolo-1' -triazole with antimicrobial properties
    • Chohan ZH, Scozzafava A, Supuran CT. Unsymmetrical 1,1' - disubstituted ferrocenes: synthesis of Co(ii), Cu(ii), Ni(ii) and Zn(ii) chelates of ferrocenyl-1-thiadiazolo-1' -tetrazole, -1-thiadiazolo-1' - triazole and -1-tetrazolo-1' -triazole with antimicrobial properties. J Enzyme Inhib Med Chem 2002;17:261-6.
    • (2002) J Enzyme Inhib Med Chem , vol.17 , pp. 261-266
    • Chohan, Z.H.1    Scozzafava, A.2    Supuran, C.T.3
  • 17
    • 80053563164 scopus 로고    scopus 로고
    • Interfering with pH regulation in tumours as a therapeutic strategy
    • Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767-77.
    • (2011) Nat Rev Drug Discov , vol.10 , pp. 767-777
    • Neri, D.1    Supuran, C.T.2
  • 18
    • 84859870939 scopus 로고    scopus 로고
    • Recent development in targeting carbonic anhydrase IX for cancer therapeutics
    • McDonald PC, Winum JY, Supuran CT, Dedhar S. Recent development in targeting carbonic anhydrase IX for cancer therapeutics. Oncotarget 2012;3:84-97.
    • (2012) Oncotarget , vol.3 , pp. 84-97
    • McDonald, P.C.1    Winum, J.Y.2    Supuran, C.T.3    Dedhar, S.4
  • 19
    • 77953521863 scopus 로고    scopus 로고
    • Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII
    • Guler OO, De Simone G, Supuran CT. Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII. Curr Med Chem 2010;17:1516-26.
    • (2010) Curr Med Chem , vol.17 , pp. 1516-1526
    • Guler, O.O.1    De Simone, G.2    Supuran, C.T.3
  • 20
    • 84872343989 scopus 로고    scopus 로고
    • Sulfocoumarins (1,2-benzoxathiine-2,2-dioxides): A class of potent and isoform-selective inhibitors of tumor-associated carbonic anhydrases
    • Tars K, Vullo D, Kazaks A, et al. Sulfocoumarins (1,2-benzoxathiine-2,2-dioxides): a class of potent and isoform-selective inhibitors of tumor-associated carbonic anhydrases. J Med Chem 2013;56:293-300.
    • (2013) J Med Chem , vol.56 , pp. 293-300
    • Tars, K.1    Vullo, D.2    Kazaks, A.3
  • 21
    • 84973433057 scopus 로고    scopus 로고
    • New series of sulfonamides containing amino acid moiety act as a effective and selective inhibitors of tumor-associated carbonic anhydrase XII
    • Ceruso M, Bragagni M, AlOthman Z, et al. New series of sulfonamides containing amino acid moiety act as a effective and selective inhibitors of tumor-associated carbonic anhydrase XII. J Enzyme Inhib Med Chem 2014;4:1-5.
    • (2014) J Enzyme Inhib Med Chem , vol.4 , pp. 1-5
    • Ceruso, M.1    Bragagni, M.2    AlOthman, Z.3
  • 23
    • 40549102791 scopus 로고    scopus 로고
    • Cyclisation/fluorination of nitrogen containing dienes in superacid HF-SbF5: A new route to 3- and 4-fluoropiperidines
    • Vardelle E, Gamba-Sanchez D, Martin-Mingot A, et al. Cyclisation/fluorination of nitrogen containing dienes in superacid HF-SbF5: a new route to 3- and 4-fluoropiperidines. Chem Commun 2008: 1473-5.
    • (2008) Chem Commun , pp. 1473-1475
    • Vardelle, E.1    Gamba-Sanchez, D.2    Martin-Mingot, A.3
  • 25
    • 84861697802 scopus 로고    scopus 로고
    • Anti-Markovnikov additions to N-allylic derivatives involving ammonium-carbenium superelectrophiles
    • Compain G, Martin-Mingot A, Frapper G, et al. Anti-Markovnikov additions to N-allylic derivatives involving ammonium-carbenium superelectrophiles. Chem Commun 2012;48:5877-9.
    • (2012) Chem Commun , vol.48 , pp. 5877-5879
    • Compain, G.1    Martin-Mingot, A.2    Frapper, G.3
  • 26
    • 84860356795 scopus 로고    scopus 로고
    • Stereoselective hydrofluorination of ynamides: A straightforward synthesis of novel α-fluoroenamides
    • Compain G, Jouvin K, Martin-Mingot A, et al. Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel α-fluoroenamides. Chem Commun 2012;48:5196-8.
    • (2012) Chem Commun , vol.48 , pp. 5196-5198
    • Compain, G.1    Jouvin, K.2    Martin-Mingot, A.3
  • 27
    • 84879036120 scopus 로고    scopus 로고
    • New superacid synthesized (fluorinated) tertiary benzenesulfonamides acting as selective hCA IX inhibitors: Toward a new mode of carbonic anhydrase inhibition by sulfonamides
    • Métayer B, Mingot A, Vullo D, et al. New superacid synthesized (fluorinated) tertiary benzenesulfonamides acting as selective hCA IX inhibitors: toward a new mode of carbonic anhydrase inhibition by sulfonamides. Chem Commun 2013;49:6015-17.
    • (2013) Chem Commun , vol.49 , pp. 6015-6017
    • Métayer, B.1    Mingot, A.2    Vullo, D.3
  • 28
    • 84886926777 scopus 로고    scopus 로고
    • Superacid synthesized tertiary benzenesulfonamides and benzofuzed sultams act as selective hCA IX inhibitors: Toward understanding a new mode of inhibition by tertiary sulfonamides
    • Métayer B, Mingot A, Vullo D, et al. Superacid synthesized tertiary benzenesulfonamides and benzofuzed sultams act as selective hCA IX inhibitors: toward understanding a new mode of inhibition by tertiary sulfonamides. Org Biomol Chem 2013;43:7540-9.
    • (2013) Org Biomol Chem , vol.43 , pp. 7540-7549
    • Métayer, B.1    Mingot, A.2    Vullo, D.3
  • 29
    • 84874526005 scopus 로고    scopus 로고
    • Superacid synthesis of halogen containing N-substituted-4-aminobenzene sulfonamides: New selective tumor-associated carbonic anhydrase inhibitors
    • Compain G, Martin-Mingot A, Maresca A, et al. Superacid synthesis of halogen containing N-substituted-4-aminobenzene sulfonamides: new selective tumor-associated carbonic anhydrase inhibitors. Bioorg Med Chem 2013;21:1555-63.
    • (2013) Bioorg Med Chem , vol.21 , pp. 1555-1563
    • Compain, G.1    Martin-Mingot, A.2    Maresca, A.3
  • 30
    • 78449303755 scopus 로고    scopus 로고
    • 7,8-disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/subnanomolar range
    • Maresca A, Scozzafava A, Supuran CT. 7,8-disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/subnanomolar range. Bioorg Med Chem Lett 2010;20:7255-8.
    • (2010) Bioorg Med Chem Lett , vol.20 , pp. 7255-7258
    • Maresca, A.1    Scozzafava, A.2    Supuran, C.T.3
  • 31
    • 77955424195 scopus 로고    scopus 로고
    • Coumarins incorporating hydroxyl- and chloro-moities selectively inhibit the transmembrane tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II
    • Maresca A, Supuran CT. Coumarins incorporating hydroxyl- and chloro-moities selectively inhibit the transmembrane tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II. Bioorg Med Chem Lett 2010;20:4511-14.
    • (2010) Bioorg Med Chem Lett , vol.20 , pp. 4511-4514
    • Maresca, A.1    Supuran, C.T.2
  • 32
    • 84896697813 scopus 로고    scopus 로고
    • Synthesis of 6-tetrazolyl-substituted sulfocoumarins acting as highly potent and selective inhibitors of the tumor-associated carbonic anhydrase isoforms IX and XII
    • Grandane A, Tanc M, Zalubovskis R, Supuran CT. Synthesis of 6-tetrazolyl-substituted sulfocoumarins acting as highly potent and selective inhibitors of the tumor-associated carbonic anhydrase isoforms IX and XII. Bioorg Med Chem 2014;22:1522-8.
    • (2014) Bioorg Med Chem , vol.22 , pp. 1522-1528
    • Grandane, A.1    Tanc, M.2    Zalubovskis, R.3    Supuran, C.T.4
  • 33
    • 84902535493 scopus 로고    scopus 로고
    • Synthesis and evaluation of (18)F-labeled tertiary benzenesulfonamides for imaging carbonic anhydrase IX expression in tumours with positron emission tomography
    • Lau J, Pan J, Zhang Z, et al. Synthesis and evaluation of (18)F-labeled tertiary benzenesulfonamides for imaging carbonic anhydrase IX expression in tumours with positron emission tomography. Bioorg Med Chem Lett 2014;24:3064-8.
    • (2014) Bioorg Med Chem Lett , vol.24 , pp. 3064-3068
    • Lau, J.1    Pan, J.2    Zhang, Z.3
  • 34
    • 84896720529 scopus 로고    scopus 로고
    • Design, synthesis and evaluation of N-substituted saccharin derivatives as selective inhibitors of tumor-associated carbonic anhydrase XII
    • D'Ascenzio M, Carradori S, De Monte C, et al. Design, synthesis and evaluation of N-substituted saccharin derivatives as selective inhibitors of tumor-associated carbonic anhydrase XII. Bioorg Med Chem 2014;22:1821-31.
    • (2014) Bioorg Med Chem , vol.22 , pp. 1821-1831
    • D'Ascenzio, M.1    Carradori, S.2    De Monte, C.3
  • 35
    • 67749116253 scopus 로고    scopus 로고
    • Non-zinc mediated inhibition of carbonic anhydrases: Coumarins are a new class of suicide inhibitors
    • Maresca A, Temperini C, Vu H, et al. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. J Am Chem Soc 2009;131:3057-62.
    • (2009) J Am Chem Soc , vol.131 , pp. 3057-3062
    • Maresca, A.1    Temperini, C.2    Vu, H.3
  • 36
    • 77249175356 scopus 로고    scopus 로고
    • The coumarin-binding site in carbonic anhydrase accomodates structurally diverse inhibitors: The antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors
    • Temperini C, Innocenti A, Scozzafava A, et al. The coumarin-binding site in carbonic anhydrase accomodates structurally diverse inhibitors: the antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors. J Med Chem 2010;53:850-4.
    • (2010) J Med Chem , vol.53 , pp. 850-854
    • Temperini, C.1    Innocenti, A.2    Scozzafava, A.3
  • 37
    • 79958247146 scopus 로고    scopus 로고
    • Conformational variability of different sulfonamide inhibitors with thienyl-acetamido moieties attributes to different binding in the active site of the cytosolic human carbonic anhydrase isoforms
    • Biswas S, Aggarwal M, Güzel Ö, et al. Conformational variability of different sulfonamide inhibitors with thienyl-acetamido moieties attributes to different binding in the active site of the cytosolic human carbonic anhydrase isoforms. Bioorg Med Chem 2011;19: 3732-8.
    • (2011) Bioorg Med Chem , vol.19 , pp. 3732-3738
    • Biswas, S.1    Aggarwal, M.2    Güzel, Ö.3
  • 38
    • 0347360282 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride
    • Abbate F, Coetzee A, Casini A, et al. Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride. Bioorg Med Chem Lett 2004; 14:337-41.
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 337-341
    • Abbate, F.1    Coetzee, A.2    Casini, A.3
  • 39
    • 0043198517 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the perfluorobenzoyl analogue of methazolamide: Implications for the drug design of fluorinated inhibitors
    • Abbate F, Casini A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the perfluorobenzoyl analogue of methazolamide: implications for the drug design of fluorinated inhibitors. J Enzyme Inhib Med Chem 2003;18:303-8.
    • (2003) J Enzyme Inhib Med Chem , vol.18 , pp. 303-308
    • Abbate, F.1    Casini, A.2    Scozzafava, A.3    Supuran, C.T.4
  • 41
    • 84897584974 scopus 로고    scopus 로고
    • Fluorine in pharmaceutical industry: Fluorine-containing drugs introduced to the market in the last decade (2001-2011)
    • Wang J, Sanchez-Rosello M, Acena JL, et al. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011). Chem Rev 2014;114:2432-506.
    • (2014) Chem Rev , vol.114 , pp. 2432-2506
    • Wang, J.1    Sanchez-Rosello, M.2    Acena, J.L.3
  • 42
    • 34848921683 scopus 로고    scopus 로고
    • Predicting and tuning physiochemical properties in lead optimization: Amine basicities
    • Morgenthaler M, Schweiser E, Hoffman-Röder A, et al. Predicting and tuning physiochemical properties in lead optimization: amine basicities. Chem Med Chem 2007;2:1100-15.
    • (2007) Chem Med Chem , vol.2 , pp. 1100-1115
    • Morgenthaler, M.1    Schweiser, E.2    Hoffman-Röder, A.3
  • 43
    • 34848848499 scopus 로고    scopus 로고
    • Fluorine in pharmaceuticals: Looking beyond intuition
    • Müller K, Faeh C, Diederich F. Fluorine in pharmaceuticals: looking beyond intuition. Science 2007;317:1881-6.
    • (2007) Science , vol.317 , pp. 1881-1886
    • Müller, K.1    Faeh, C.2    Diederich, F.3
  • 45
    • 84890462953 scopus 로고    scopus 로고
    • Stereoselectively fluorinated N-heterocycles: A brief survey
    • Hu X-G, Hunter L. Stereoselectively fluorinated N-heterocycles: a brief survey. Beilstein J Org Chem 2013;9:2696-708.
    • (2013) Beilstein J Org Chem , vol.9 , pp. 2696-2708
    • Hu, X.-G.1    Hunter, L.2
  • 46
    • 77952688640 scopus 로고    scopus 로고
    • The C-F bond as a conformational tool in organic and biological chemistry
    • Hunter L. The C-F bond as a conformational tool in organic and biological chemistry. Beilstein J Org Chem 2010;6:38.
    • (2010) Beilstein J Org Chem , vol.6 , pp. 38
    • Hunter, L.1
  • 48
    • 84907056586 scopus 로고    scopus 로고
    • Sulfonamides incorporating fluorine and 1,3,5-triazine moieties are effective inhibitors of three β-class carbonic anhydrases from Mycobacterium tuberculosis
    • Ceruso M, Vullo D, Scozzafava A, Supuran CT. Sulfonamides incorporating fluorine and 1,3,5-triazine moieties are effective inhibitors of three β-class carbonic anhydrases from Mycobacterium tuberculosis. J Enzyme Inhib Med Chem 2014;25:686-9.
    • (2014) J Enzyme Inhib Med Chem , vol.25 , pp. 686-689
    • Ceruso, M.1    Vullo, D.2    Scozzafava, A.3    Supuran, C.T.4
  • 49
    • 0015239422 scopus 로고
    • Carbon dioxide hydratation activity of carbonic anhydrase: Kinetics of alkylated anhydrases B and C from humans
    • Khalifah RG. Carbon dioxide hydratation activity of carbonic anhydrase: kinetics of alkylated anhydrases B and C from humans. J Biol Chem 1971;246:2561-73.
    • (1971) J Biol Chem , vol.246 , pp. 2561-2573
    • Khalifah, R.G.1
  • 50
    • 79955566849 scopus 로고    scopus 로고
    • Sulfonamides incorporating boroxazolidone moieties are potent inhibitors of the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII
    • Rami M, Maresca A, Smaine F-Z, et al. Sulfonamides incorporating boroxazolidone moieties are potent inhibitors of the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII. Bioorg Med Chem Lett 2011;21:2975-9.
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 2975-2979
    • Rami, M.1    Maresca, A.2    Smaine, F.-Z.3
  • 51
    • 77958011621 scopus 로고    scopus 로고
    • Indapamide-like benzenesulfonamides as inhibitors of carbonic anhydrases I, II, VII, and XIII
    • Capkauskaite E, Baranauskiene L, Golovenko D, et al. Indapamide-like benzenesulfonamides as inhibitors of carbonic anhydrases I, II, VII, and XIII. Bioorg Med Chem 2010;18:7357-64.
    • (2010) Bioorg Med Chem , vol.18 , pp. 7357-7364
    • Capkauskaite, E.1    Baranauskiene, L.2    Golovenko, D.3
  • 52
    • 79953791531 scopus 로고    scopus 로고
    • Structural basis for the interaction between carbonic anhydrase and 1,2,3,4-tetrahydroisoquinolin-2-ylsulfonamides
    • Mader P, Brynda J, Gitto R, et al. Structural basis for the interaction between carbonic anhydrase and 1,2,3,4-tetrahydroisoquinolin-2-ylsulfonamides. J Med Chem 2011;54:2522-6.
    • (2011) J Med Chem , vol.54 , pp. 2522-2526
    • Mader, P.1    Brynda, J.2    Gitto, R.3
  • 53
    • 79956062824 scopus 로고    scopus 로고
    • Synthesis and crystallographic analysis of new sulfonamides incorporating NO-donating moieties with potent antiglaucoma action
    • Mincione F, Benedini F, Biondi S, et al. Synthesis and crystallographic analysis of new sulfonamides incorporating NO-donating moieties with potent antiglaucoma action. Bioorg Med Chem Lett 2011;21:3216-21 .
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 3216-3221
    • Mincione, F.1    Benedini, F.2    Biondi, S.3
  • 54
    • 78651253336 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition studies with anions and sulfonamides of a new cytosolic enzyme from the scleractinian coral Stylophora pistillata
    • Bertucci A, Innocenti A, Scozzafava A, et al. Carbonic anhydrase inhibitors. Inhibition studies with anions and sulfonamides of a new cytosolic enzyme from the scleractinian coral Stylophora pistillata. Bioorg Med Chem Lett 2011;21:710-14.
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 710-714
    • Bertucci, A.1    Innocenti, A.2    Scozzafava, A.3
  • 55
    • 79958174646 scopus 로고    scopus 로고
    • Anticonvulsant 4-aminobenzenesulfonamide derivatives with branched-alkylamide moieties: X-ray crystallography and inhibition studies of human carbonic anhydrase isoforms I, II, VII, and XIV
    • Hen N, Bialer M, Yagen B, et al. Anticonvulsant 4-aminobenzenesulfonamide derivatives with branched-alkylamide moieties: X-ray crystallography and inhibition studies of human carbonic anhydrase isoforms I, II, VII, and XIV. J Med Chem 2011;54: 3977-81.
    • (2011) J Med Chem , vol.54 , pp. 3977-3981
    • Hen, N.1    Bialer, M.2    Yagen, B.3
  • 56
    • 0037596704 scopus 로고    scopus 로고
    • Effect of anti-carbonic anhydrase antibodies on carbonic anhydrases I and II
    • Botrè F, Botrè C, Podestà E, et al. Effect of anti-carbonic anhydrase antibodies on carbonic anhydrases I and II. Clin Chem 2003;49: 1221-3.
    • (2003) Clin Chem , vol.49 , pp. 1221-1223
    • Botrè, F.1    Botrè, C.2    Podestà, E.3
  • 57
    • 83755205958 scopus 로고    scopus 로고
    • The neurology of carbonic anhydrase type II deficiency syndrome
    • Bosley TM, Salih MA, Alorainy IA, et al. The neurology of carbonic anhydrase type II deficiency syndrome. Brain 2011;134: 3499-512.
    • (2011) Brain , vol.134 , pp. 3499-3512
    • Bosley, T.M.1    Salih, M.A.2    Alorainy, I.A.3


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