메뉴 건너뛰기




Volumn 27, Issue 6, 2012, Pages 886-891

Carbonic Anhydrases inhibitory effects of new benzenesulfonamides synthesized by using superacid chemistry

Author keywords

Fluorine chemistry; Hypoxic tumors; Sultams; Superelectrophiles

Indexed keywords

ANTIMONY DERIVATIVE; BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE XII; CHLORTALIDONE; FLUORINE DERIVATIVE; FUROSEMIDE; HYDROFLUORIC ACID; INDAPAMIDE; ISOENZYME;

EID: 84870516777     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.638921     Document Type: Article
Times cited : (72)

References (32)
  • 1
    • 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 Discov 2008;7:168-181.
    • (2008) Nat Rev Drug Discov , vol.7 , pp. 168-181
    • Supuran, C.T.1
  • 3
    • 42549148009 scopus 로고    scopus 로고
    • Carbonic anhydrase IX: A new druggable target for the design of antitumor agents
    • Winum JY, Rami M, Scozzafava A, Montero JL, Supuran C. Carbonic anhydrase IX: A new druggable target for the design of antitumor agents. Med Res Rev 2008;28:445-463.
    • (2008) Med Res Rev , vol.28 , pp. 445-463
    • Winum, J.Y.1    Rami, M.2    Scozzafava, A.3    Montero, J.L.4    Supuran, C.5
  • 6
    • 34248659399 scopus 로고    scopus 로고
    • Carbonic anhydrases as targets for medicinal chemistry
    • Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336-4350.
    • (2007) Bioorg Med Chem , vol.15 , pp. 4336-4350
    • Supuran, C.T.1    Scozzafava, A.2
  • 7
    • 78649857406 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibition/activation: Trip of a scientist around the world in the search of novel chemotypes and drug targets
    • Supuran CT. Carbonic anhydrase inhibition/activation: Trip of a scientist around the world in the search of novel chemotypes and drug targets. Curr Pharm Des 2010;16:3233-3245.
    • (2010) Curr Pharm des , vol.16 , pp. 3233-3245
    • Supuran, C.T.1
  • 8
    • 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 FZ, Montero JL, Scozzafava A, Winum JY 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;21:2975-2979.
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 2975-2979
    • Rami, M.1    Maresca, A.2    Smaine, F.Z.3    Montero, J.L.4    Scozzafava, A.5    Winum, J.Y.6
  • 10
    • 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, Agnello S, Pachl P, Supuran CT et al. Structural basis for the interaction between carbonic anhydrase and 1,2,3,4-tetrahydroisoquinolin-2-ylsulfonamides. J Med Chem 2011;54:2522-2526.
    • (2011) J Med Chem , vol.54 , pp. 2522-2526
    • Mader, P.1    Brynda, J.2    Gitto, R.3    Agnello, S.4    Pachl, P.5    Supuran, C.T.6
  • 11
    • 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, Cecchi A, Temperini C, Formicola G et al. Synthesis and crystallographic analysis of new sulfonamides incorporating NO-donating moieties with potent antiglaucoma action. Bioorg Med Chem Lett 2011;21:3216-3221.
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 3216-3221
    • Mincione, F.1    Benedini, F.2    Biondi, S.3    Cecchi, A.4    Temperini, C.5    Formicola, G.6
  • 12
    • 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, Tambutté S, Zoccola D, Supuran CT. 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;21:710-714.
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 710-714
    • Bertucci, A.1    Innocenti, A.2    Scozzafava, A.3    Tambutté, S.4    Zoccola, D.5    Supuran, C.T.6
  • 13
    • 77954218410 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors
    • Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467-3474.
    • (2010) Bioorg Med Chem Lett , vol.20 , pp. 3467-3474
    • Supuran, C.T.1
  • 15
    • 0015239422 scopus 로고
    • The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C
    • Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971;246:2561-2573.
    • (1971) J Biol Chem , vol.246 , pp. 2561-2573
    • Khalifah, R.G.1
  • 16
    • 0037911231 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives
    • Ilies MA, Vullo D, Pastorek J, Scozzafava A, Ilies M, Caproiu MT et al. Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives. J Med Chem 2003;46:2187-2196.
    • (2003) J Med Chem , vol.46 , pp. 2187-2196
    • Ilies, M.A.1    Vullo, D.2    Pastorek, J.3    Scozzafava, A.4    Ilies, M.5    Caproiu, M.T.6
  • 17
    • 79958247146 scopus 로고    scopus 로고
    • Conformational variability of different sulfonamide inhibitors with thienyl-acetamido moieties attributes to differential binding in the active site of cytosolic human carbonic anhydrase isoforms
    • Biswas S, Aggarwal M, Güzel Ö, Scozzafava A, McKenna R, Supuran CT. Conformational variability of different sulfonamide inhibitors with thienyl-acetamido moieties attributes to differential binding in the active site of cytosolic human carbonic anhydrase isoforms. Bioorg Med Chem 2011;19:3732-3738.
    • (2011) Bioorg Med Chem , vol.19 , pp. 3732-3738
    • Biswas, S.1    Aggarwal, M.2    Güzel, Ö.3    Scozzafava, A.4    McKenna, R.5    Supuran, C.T.6
  • 18
    • 85103036295 scopus 로고    scopus 로고
    • Organic synthesis in superacid
    • Olah GA, (ed). New York: Wiley;
    • Jacquesy J-C. Organic Synthesis in Superacid. In: Olah GA, (ed). Carbocation Chemistry. New York: Wiley; 2009. pp 359-376.
    • (2009) Carbocation Chemistry , pp. 359-376
    • Jacquesy, J.-C.1
  • 19
    • 34547408893 scopus 로고    scopus 로고
    • A novel, facile route to β-fluoroamines by hydrofluorination reaction in superacid HF-SbF5
    • Thibaudeau S, Martin-Mingot A, Jouannetaud M-P, Karam O, Zunino F. A novel, facile route to β-fluoroamines by hydrofluorination reaction in superacid HF-SbF5. Chem Commun 2007;3198-3200.
    • (2007) Chem Commun , pp. 3198-3200
    • Thibaudeau, S.1    Martin-Mingot, A.2    Jouannetaud, M.-P.3    Karam, O.4    Zunino, F.5
  • 20
    • 40549102791 scopus 로고    scopus 로고
    • Cyclisation/fluoriantion of nitrogen containing dienes in superacid HF-SbF5 : A new route to 3- and 4-fluoropiperidines
    • Vardelle E, Gamba-Sanchez D, Martin-Mingot A, Jouannetaud M-P, Thibaudeau S, Marrot J. Cyclisation/fluoriantion of nitrogen containing dienes in superacid HF-SbF5 : A new route to 3- and 4-fluoropiperidines. Chem Commun 2008;1473-1475.
    • (2008) Chem Commun , pp. 1473-1475
    • Vardelle, E.1    Gamba-Sanchez, D.2    Martin-Mingot, A.3    Jouannetaud, M.-P.4    Thibaudeau, S.5    Marrot, J.6
  • 23
    • 76849095061 scopus 로고    scopus 로고
    • Superelectrophilic activation in superacid HF/SbF(5) and synthesis of benzofused sultams
    • Liu F, Martin-Mingot A, Jouannetaud MP, Zunino F, Thibaudeau S. Superelectrophilic activation in superacid HF/SbF(5) and synthesis of benzofused sultams. Org Lett 2010;12:868-871.
    • (2010) Org Lett , vol.12 , pp. 868-871
    • Liu, F.1    Martin-Mingot, A.2    Jouannetaud, M.P.3    Zunino, F.4    Thibaudeau, S.5
  • 25
    • 77955419223 scopus 로고    scopus 로고
    • Superacid mediated reactions applied to 4-aminobenzofused sultams and fluorinated 4-aminobenzene sulfonamides synthesis
    • Liu F, Musadji NY, Lecornué F, Jouannetaud M-P, Thibaudeau S. Superacid mediated reactions applied to 4-aminobenzofused sultams and fluorinated 4-aminobenzene sulfonamides synthesis. Tetrahedron 2010;66:7112-7118.
    • (2010) Tetrahedron , vol.66 , pp. 7112-7118
    • Liu, F.1    Musadji, N.Y.2    Lecornué, F.3    Jouannetaud, M.-P.4    Thibaudeau, S.5
  • 26
    • 44949190364 scopus 로고    scopus 로고
    • Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs
    • Thiry A, Supuran CT, Masereel B, Dogné JM. Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs. J Med Chem 2008;51:3051-3056.
    • (2008) J Med Chem , vol.51 , pp. 3051-3056
    • Thiry, A.1    Supuran, C.T.2    Masereel, B.3    Dogné, J.M.4
  • 27
    • 70349490906 scopus 로고    scopus 로고
    • Crystal structure of the catalytic domain of the tumorassociated human carbonic anhydrase IX
    • Alterio V, Hilvo M, Di Fiore A, Supuran CT, Pan P, Parkkila S et al. Crystal structure of the catalytic domain of the tumorassociated human carbonic anhydrase IX. Proc Natl Acad Sci USA 2009;106:16233-16238.
    • (2009) Proc Natl Acad Sci USA , vol.106 , pp. 16233-16238
    • Alterio, V.1    Hilvo, M.2    Di Fiore, A.3    Supuran, C.T.4    Pan, P.5    Parkkila, S.6
  • 28
    • 1842790839 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozyme IX with fluorine-containing sulfonamides. The first subnanomolar CA IX inhibitor discovered
    • Vullo D, Scozzafava A, Pastorekova S, Pastorek J, Supuran CT. Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozyme IX with fluorine-containing sulfonamides. The first subnanomolar CA IX inhibitor discovered. Bioorg Med Chem Lett 2004;14:2351-2356.
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 2351-2356
    • Vullo, D.1    Scozzafava, A.2    Pastorekova, S.3    Pastorek, J.4    Supuran, C.T.5
  • 29
    • 38149016915 scopus 로고    scopus 로고
    • Understanding organofluorine chemistry. An introduction to the C-F bond
    • O'Hagan D. Understanding organofluorine chemistry. An introduction to the C-F bond. Chem Soc Rev 2008;37:308-319.
    • (2008) Chem Soc Rev , vol.37 , pp. 308-319
    • O'Hagan, D.1
  • 30
    • 12844263538 scopus 로고    scopus 로고
    • Synthesis of alpha-fluoro- and alpha, alpha-difluoro- benzenemethanesulfonamides: New inhibitors of carbonic anhydrase
    • Blackburn GM, Türkmen H. Synthesis of alpha-fluoro- and alpha, alpha-difluoro-benzenemethanesulfonamides: New inhibitors of carbonic anhydrase. Org Biomol Chem 2005;3:225-226.
    • (2005) Org Biomol Chem , vol.3 , pp. 225-226
    • Blackburn, G.M.1    Türkmen, H.2
  • 32
    • 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;10:767-777.
    • (2011) Nat Rev Drug Discov , vol.10 , pp. 767-777
    • Neri, D.1    Supuran, C.T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.