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Volumn 82, Issue , 2014, Pages 47-55

Carbonic anhydrase inhibitors. Synthesis of a novel series of 5-substituted 2,4-dichlorobenzenesulfonamides and their inhibition of human cytosolic isozymes i and II and the transmembrane tumor-associated isozymes IX and XII

Author keywords

2,4 Dichlorobenzenesulfonamides; Carbonic anhydrase isozymes I, II, IX and XII inhibitors; Synthesis

Indexed keywords

2,4 DICHLORO 5 (2 BENZOYLHYDRAZINECARBONYL)BENZENESULFONAMIDE; 2,4 DICHLORO 5 (3 PHENYLUREIDO)BENZENESULFONAMIDE; 2,4 DICHLORO 5 (5 PHENYL 1,2,4 TRIAZOL 3 YL)BENZENESULFONAMIDE; 2,4 DICHLORO 5 (5 PHENYL 1,3,4 OXADIAZOL 2 YL)BENZENESULFONAMIDE; 2,4 DICHLORO 5 (5 PHENYL 1,3,4 THIADIAZOL 2 YL)BENZENESULFONAMIDE; 2,4 DICHLORO 5 ISOCYANATOBENZENESULFONAMIDE; 2,4 DICHLORO 5 SULFAMOYLBENZOYL AZIDE; 2,4 DICHLORO 5 [2 (4 CHLOROBENZOYL)HYDRAZINECARBONYL]BENZENESULFONAMIDE; 2,4 DICHLORO 5 [2 (4 METHYLBENZOYL)HYDRAZINECARBONYL]BENZENESULFONAMIDE; 2,4 DICHLORO 5 [2 (FURAN 2 CARBONYL)HYDRAZINECARBONYL]BENZENESULFONAMIDE; 2,4 DICHLORO 5 [3 (3 MORPHOLINOPROPYL)UREIDO]BENZENESULFONAMIDE; 2,4 DICHLORO 5 [3 (4 CHLOROPHENYL)UREIDO]BENZENESULFONAMIDE; 2,4 DICHLORO 5 [3 (4 SULFAMOYLPHENYL)UREIDO]BENZENESULFONAMIDE; 2,4 DICHLORO 5 [5 (4 CHLOROPHENYL) 1,2,4 TRIAZOL 3 YL]BENZENESULFONAMIDE; 2,4 DICHLORO 5 [5 (4 CHLOROPHENYL) 1,3,4 OXADIAZOL 2 YL]BENZENESULFONAMIDE; 2,4 DICHLORO 5 [5 (4 CHLOROPHENYLAMINO) 1,3,4 OXADIAZOL 2 YL]BENZENESULFONAMIDE; 2,4 DICHLORO 5 [5 (4 METHYLPHENYL) 1,3,4 OXADIAZOL 2 YL]BENZENESULFONAMIDE; 2,4 DICHLORO 5 [5 (PHENYLAMINO) 1,3,4 OXADIAZOL 2 YL]BENZENESULFONAMIDE; 4 (BENZODIOXOL 5 YLMETHYL)N(2,4 DICHLORO 5 SULFAMOYLPHENYL)PIPERAZINE 1 CARBOXAMIDE; 5 (3 BENZYLUREIDO) 2,4 DICHLOROBENZENESULFONAMIDE; 5 [2 (BENZOYLHYDRAZINECARBONYL) 2,4 DICHLOROBENZENESULFONAMIDE; 5 [3 (1H INDOL 1 YL)UREIDO] 2,4 DICHLOROBENZENESULFONAMIDE; 5 [3 (BENZYLOXY)UREIDO] 2,4 DICHLOROBENZENESULFONAMIDE; BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE XII; N(2,4 DICHLORO 5 SULFAMOYLBENZOYL)N''(4 CHLOROPHENYL)THIOSEMICARBAZIDE; N(2,4 DICHLORO 5 SULFAMOYLBENZOYL)N''(PHENYL)THIOSEMICARBAZIDE; UNCLASSIFIED DRUG; CARBONATE DEHYDRATASE; ISOENZYME; SULFONAMIDE;

EID: 84901422514     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.05.039     Document Type: Article
Times cited : (23)

References (48)
  • 1
    • 37149030424 scopus 로고    scopus 로고
    • Endpoints and other considerations in phase I studies of targeted anticancer therapy: Recommendations from the task force on Methodology for the Development of Innovative Cancer Therapies (MDICT)
    • DOI 10.1016/j.ejca.2007.07.034, PII S0959804907005898
    • C.M. Booth, A.H. Calvert, G. Giaccone, M.W. Lobbezoo, L.K. Seymour, and E.A. Eisenhauer Endpoints and other considerations in phase I studies of targeted anticancer therapy: recommendations from the task force on Methodology for the Development of Innovative Cancer Therapies (MDICT) EJC 44 2008 19 24 (Pubitemid 350256933)
    • (2008) European Journal of Cancer , vol.44 , Issue.1 , pp. 19-24
    • Booth, C.M.1    Calvert, A.H.2    Giaccone, G.3    Lobbezoo, M.W.4    Seymour, L.K.5    Eisenhauer, E.A.6
  • 2
    • 80053563164 scopus 로고    scopus 로고
    • Interfering with pH regulation in tumours as a therapeutic strategy
    • D. Neri, and C.T. Supuran Interfering with pH regulation in tumours as a therapeutic strategy Nat. Rev. Drug. Discov. 10 2011 767 777
    • (2011) Nat. Rev. Drug. Discov. , vol.10 , pp. 767-777
    • Neri, D.1    Supuran, C.T.2
  • 3
    • 38849143765 scopus 로고    scopus 로고
    • Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators
    • DOI 10.1038/nrd2467, PII NRD2467
    • C.T. Supuran Carbonic anhydrases: novel therapeutic applications for inhibitors and activators Nat. Rev. Drug. Discov. 7 2008 168 181 (Pubitemid 351194064)
    • (2008) Nature Reviews Drug Discovery , vol.7 , Issue.2 , pp. 168-181
    • Supuran, C.T.1
  • 4
    • 1242318777 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme v with aromatic and heterocyclic sulfonamides
    • DOI 10.1021/jm031057+
    • D. Vullo, M. Franchi, E. Gallori, J. Antel, A. Scozzafava, and C.T. Supuran Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides J. Med. Chem. 47 2004 1272 1279 (Pubitemid 38229129)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.5 , pp. 1272-1279
    • Vullo, D.1    Franchi, M.2    Gallori, E.3    Antel, J.4    Scozzafava, A.5    Supuran, C.T.6
  • 5
    • 28144452672 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors
    • DOI 10.1021/jm050483n
    • I. Nishimori, D. Vullo, A. Innocenti, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors J. Med. Chem. 48 2005 7860 7866 (Pubitemid 41698823)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.24 , pp. 7860-7866
    • Nishimori, I.1    Vullo, D.2    Innocenti, A.3    Scozzafava, A.4    Mastrolorenzo, A.5    Supuran, C.T.6
  • 6
    • 33846458646 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors
    • DOI 10.1021/jm0612057
    • I. Nishimori, T. Minakuchi, S. Onishi, D. Vullo, A. Scozzafava, and C.T. Supuran Carbonic anhydrase inhibitors. DNA cloning, characterization and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors J. Med. Chem. 50 2007 381 388 (Pubitemid 46147718)
    • (2007) Journal of Medicinal Chemistry , vol.50 , Issue.2 , pp. 381-388
    • Nishimori, I.1    Minakuchi, T.2    Onishi, S.3    Vullo, D.4    Scozzafava, A.5    Supuran, C.T.6
  • 8
    • 14844356668 scopus 로고    scopus 로고
    • Acatalytic CAs: Carbonic anhydrase-related proteins
    • C.T. Supuran, A. Scozzafava, J. Conway, CRC Press Boca Raton
    • I. Nishimori Acatalytic CAs: carbonic anhydrase-related proteins C.T. Supuran, A. Scozzafava, J. Conway, Carbonic Anhydrase - its Inhibitors and Activators 2004 CRC Press Boca Raton 25 43
    • (2004) Carbonic Anhydrase - Its Inhibitors and Activators , pp. 25-43
    • Nishimori, I.1
  • 10
    • 16244377468 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides - A new target for the design of antitumor and antiglaucoma drugs?
    • DOI 10.1016/j.bmcl.2004.12.053
    • D. Vullo, A. Innocenti, I. Nishimori, J. Pastorek, A. Scozzafava, S. Pastoreková, and C.T. Supuran Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides - a new target for the design of antitumor and antiglaucoma drugs? Bioorg. Med. Chem. Lett. 15 2005 963 969 (Pubitemid 40458631)
    • (2005) Bioorganic and Medicinal Chemistry Letters , vol.15 , Issue.4 , pp. 963-969
    • Vullo, D.1    Innocenti, A.2    Nishimori, I.3    Pastorek, J.4    Scozzafava, A.5    Pastorekova, S.6    Supuran, C.T.7
  • 12
    • 33745644458 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX
    • DOI 10.1021/ja061574s
    • V. Alterio, R.M. Vitale, S.M. Monti, C. Pedone, A. Scozzafava, A. Cecchi, G. De Simone, and C.T. Supuran Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX J. Am. Chem. Soc. 128 2006 8329 8335 (Pubitemid 43967776)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.25 , pp. 8329-8335
    • Alterio, V.1    Vitale, R.M.2    Monti, S.M.3    Pedone, C.4    Scozzafava, A.5    Cecchi, A.6    De Simone, G.7    Supuran, C.T.8
  • 14
    • 0029975564 scopus 로고    scopus 로고
    • Human MN/CA9 gene, a novel member of the carbonic anhydrase family: Structure and exon to protein domain relationships
    • DOI 10.1006/geno.1996.0223
    • R. Opavsky, S. Pastorekova, V. Zelnik, A. Gibadulinova, E.J. Stanbridge, J. Zavada, R. Kettmann, and J. Pastorek Human MN/CA9 gene, a novel member of the carbonic anhydrase family: structure and exon to protein domain relationships Genomics 33 1996 480 487 (Pubitemid 26159864)
    • (1996) Genomics , vol.33 , Issue.3 , pp. 480-487
    • Opavsky, R.1    Pastorekova, S.2    Zelnik, V.3    Gibadulinova, A.4    Stanbridge, E.J.5    Zavada, J.6    Kettmann, R.7    Pastorek, J.8
  • 16
    • 2542592581 scopus 로고    scopus 로고
    • Modulation of carbonic anhydrase activity and its applications in therapy
    • DOI 10.1517/13543776.14.5.667
    • A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran Modulation of carbonic anhydrase activity and its applications in therapy Expert Opin. Ther. Pat. 14 2004 667 702 (Pubitemid 38702328)
    • (2004) Expert Opinion on Therapeutic Patents , vol.14 , Issue.5 , pp. 667-702
    • Scozzafava, A.1    Mastrolorenzo, A.2    Supuran, C.T.3
  • 19
    • 33748079158 scopus 로고    scopus 로고
    • Tumor-associated carbonic anhydrases and their clinical significance
    • DOI 10.1016/S0065-2423(06)42005-9, PII S0065242306420059
    • S. Pastorekova, S. Parkkila, and J. Zavada Tumor-associated carbonic anhydrases and their clinical significance Adv. Clin. Chem. 42 2006 167 216 (Pubitemid 44302109)
    • (2006) Advances in Clinical Chemistry , vol.42 , pp. 167-216
    • Pastorekova, S.1    Parkkila, S.2    Zavada, J.3
  • 20
    • 34447547148 scopus 로고    scopus 로고
    • Regulation of tumor pH and the role of carbonic anhydrase 9
    • DOI 10.1007/s10555-007-9064-0, Special issue on Hypoxia and Cancer, Guest Editor: Gregg L. Semenza
    • P. Swietach, R.D. Vaughen-Jones, and A.L. Harris Regulation of tumor pH and the role of carbonic anhydrase 9 Cancer Metastasis Rev. 26 2007 299 310 (Pubitemid 47101667)
    • (2007) Cancer and Metastasis Reviews , vol.26 , Issue.2 , pp. 299-310
    • Swietach, P.1    Vaughan-Jones, R.D.2    Harris, A.L.3
  • 22
    • 84859870939 scopus 로고    scopus 로고
    • Recent developments in targeting carbonic anhydrase IX for cancer therapeutics
    • P.C. McDonald, J.Y. Winum, C.T. Supuran, and S. Dedhar Recent developments in targeting carbonic anhydrase IX for cancer therapeutics Oncotarget 3 2012 84 97
    • (2012) Oncotarget , vol.3 , pp. 84-97
    • McDonald, P.C.1    Winum, J.Y.2    Supuran, C.T.3    Dedhar, S.4
  • 23
    • 4344699403 scopus 로고    scopus 로고
    • Role of carbonic anhydrase IX in human tumor cell growth, survival, and invasion
    • DOI 10.1158/0008-5472.CAN-03-2224
    • N. Robertson, C. Potter, and A.L. Harris Role of carbonic anhydrase IX in human tumor cell growth, survival, and invasion Cancer Res. 64 2004 6160 6165 (Pubitemid 39129417)
    • (2004) Cancer Research , vol.64 , Issue.17 , pp. 6160-6165
    • Robertson, N.1    Potter, C.2    Harris, A.L.3
  • 24
    • 42549148009 scopus 로고    scopus 로고
    • Carbonic anhydrase IX: A new druggable target for the design of antitumor agents
    • DOI 10.1002/med.20112
    • J.Y. Winum, M. Rami, A. Scozzafava, J.L. Montero, and C.T. Supuran Carbonic anhydrase IX: a new drugable target for the design of antitumor agents Med. Res. Rev. 28 2008 445 463 (Pubitemid 351590542)
    • (2008) Medicinal Research Reviews , vol.28 , Issue.3 , pp. 445-463
    • Winum, J.-Y.1    Rami, M.2    Scozzafava, A.3    Montero, J.-L.4    Supuran, C.5
  • 25
    • 0001176531 scopus 로고
    • Sulphanilamide as a specific carbonic anhydrase inhibitor
    • T. Mann, and D. Keilin Sulphanilamide as a specific carbonic anhydrase inhibitor Nature 146 1940 164 165
    • (1940) Nature , vol.146 , pp. 164-165
    • Mann, T.1    Keilin, D.2
  • 26
    • 0016912115 scopus 로고
    • Relations between structure and biological activity of sulfonamides
    • T.H. Maren Relations between structure and biological activity of sulfonamides Annu. Rev. Pharmacol. Toxicol. 16 1976 309 327
    • (1976) Annu. Rev. Pharmacol. Toxicol. , vol.16 , pp. 309-327
    • Maren, T.H.1
  • 27
    • 0014135426 scopus 로고
    • Carbonic anhydrase: Chemistry, physiology and inhibition
    • T.H. Maren Carbonic anhydrase: chemistry, physiology and inhibition Physiol. Rev. 47 1967 595 781
    • (1967) Physiol. Rev. , vol.47 , pp. 595-781
    • Maren, T.H.1
  • 28
    • 0034018870 scopus 로고    scopus 로고
    • Carbonic-anhydrase inhibitors and their therapeutic potential
    • C.T. Supuran, and A. Scozzafava Carbonic anhydrase inhibitors and their therapeutic potential Exp. Opin. Ther. Pat. 10 2000 575 600 (Pubitemid 30251754)
    • (2000) Expert Opinion on Therapeutic Patents , vol.10 , Issue.5 , pp. 575-600
    • Supuran, C.T.1    Scozzafava, A.2
  • 29
    • 0034677966 scopus 로고    scopus 로고
    • Drug discovery: A historical perspective
    • J. Drew Drug discovery: a historical perspective Science 287 2000 1960 1964
    • (2000) Science , vol.287 , pp. 1960-1964
    • Drew, J.1
  • 30
    • 84878067755 scopus 로고    scopus 로고
    • Anticancer carbonic anhydrase inhibitors: A patent review (2008-2013)
    • S.M. Monti, C.T. Supuran, and G. De Simone Anticancer carbonic anhydrase inhibitors: a patent review (2008-2013) Expert Opin. Ther. Pat. 23 2013 737 749
    • (2013) Expert Opin. Ther. Pat. , vol.23 , pp. 737-749
    • Monti, S.M.1    Supuran, C.T.2    De Simone, G.3
  • 32
    • 0037315480 scopus 로고    scopus 로고
    • Indisulam: An anticancer sulfonamide in clinical development
    • DOI 10.1517/13543784.12.2.283
    • C.T. Supuran Indisulam: an anticancer sulfonamide in clinical development Expert Opin. Investig. Drugs 12 2003 283 287 (Pubitemid 36204606)
    • (2003) Expert Opinion on Investigational Drugs , vol.12 , Issue.2 , pp. 283-287
    • Supuran, C.T.1
  • 33
    • 0348147633 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX
    • DOI 10.1016/j.bmcl.2003.09.062
    • F. Abbate, A. Casini, T. Owa, A. Scozzafava, and C.T. Supuran 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. 14 2004 217 223 (Pubitemid 38010223)
    • (2004) Bioorganic and Medicinal Chemistry Letters , vol.14 , Issue.1 , pp. 217-223
    • Abbate, F.1    Casini, A.2    Owa, T.3    Scozzafava, A.4    Supuran, C.T.5
  • 34
    • 25144498040 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamides
    • DOI 10.1016/j.bmcl.2005.08.048, PII S0960894X05011029
    • Ö. Özensoy, L. Puccetti, G. Fasolis, O. Arslan, A. Scozzafava, and C.T. Supuran Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamides Bioorg. Med. Chem. Lett. 15 2005 4862 4866 (Pubitemid 41354823)
    • (2005) Bioorganic and Medicinal Chemistry Letters , vol.15 , Issue.21 , pp. 4862-4866
    • Ozensoy, O.1    Puccetti, L.2    Fasolis, G.3    Arslan, O.4    Scozzafava, A.5    Supuran, C.T.6
  • 35
    • 15444377021 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties
    • DOI 10.1021/jm0494826
    • J.Y. Winum, J.M. Dogne, A. Casini, X. de Leval, J.L. Montero, A. Scozzafava, D. Vullo, A. Innocenti, and C.T. Supuran Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties J. Med. Chem. 48 2005 2121 2125 (Pubitemid 40396340)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.6 , pp. 2121-2125
    • Winum, J.-Y.1    Dogne, J.-M.2    Casini, A.3    De Leval, X.4    Montero, J.-L.5    Scozzafava, A.6    Vullo, D.7    Innocenti, A.8    Supuran, C.T.9
  • 36
    • 79952808077 scopus 로고    scopus 로고
    • Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IC and show antimetastatic activity in a model of breast cancer metastasis
    • F. Pacchiano, F. Carta, P.C. McDonald, Y. Lou, D. Vullo, A. Scozzafava, S. Dedhar, and C.T. Supuran Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IC and show antimetastatic activity in a model of breast cancer metastasis J. Med. Chem. 54 2011 1896 1902
    • (2011) J. Med. Chem. , vol.54 , pp. 1896-1902
    • Pacchiano, F.1    Carta, F.2    McDonald, P.C.3    Lou, Y.4    Vullo, D.5    Scozzafava, A.6    Dedhar, S.7    Supuran, C.T.8
  • 37
    • 0037911231 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives
    • DOI 10.1021/jm021123s
    • M.A. Ilies, D. Vullo, J. Pastorek, A. Scozzafava, M. Ilies, M.T. Caproiu, S. Pastorekova, and C.T. Supuran Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives J. Med. Chem. 46 2003 2187 2196 (Pubitemid 36583497)
    • (2003) Journal of Medicinal Chemistry , vol.46 , Issue.11 , pp. 2187-2196
    • Ilies, M.A.1    Vullo, D.2    Pastorek, J.3    Scozzafava, A.4    Ilies, M.5    Caproiu, M.T.6    Pastorekova, S.7    Supuran, C.T.8
  • 40
    • 33746836508 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Inhibition of the cytosolic human isozymes I and II, and the transmembrane, tumor-associated isozymes IX and XII with substituted aromatic sulfonamides activatable in hypoxic tumors
    • DOI 10.1016/j.bmcl.2006.06.064, PII S0960894X06007347
    • F. Sa̧czewski, J. Sławiński, A. Kornicka, Z. Brzozowski, E. Pomarnacka, A. Innocenti, A. Scozzafava, and C.T. Supuran Carbonic anhydrase inhibitors. Inhibition of the cytosolic human isozymes I and II, and the transmembrane, tumor-associated isozymes IX and XII with substituted aromatic sulfonamides activatable in hypoxic tumors Bioorg. Med. Chem. Lett. 16 2006 4846 4851 (Pubitemid 44177775)
    • (2006) Bioorganic and Medicinal Chemistry Letters , vol.16 , Issue.18 , pp. 4846-4851
    • Saczewski, F.1    Slawinski, J.2    Kornicka, A.3    Brzozowski, Z.4    Pomarnacka, E.5    Innocenti, A.6    Scozzafava, A.7    Supuran, C.T.8
  • 41
    • 33751100628 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Selective inhibition of human tumor-associated isozymes IX and XII and cytosolic isozymes I and II with some substituted-2-mercapto-benzenesulfonamides
    • DOI 10.1080/14756360600648146, PII GK2589H06026KN79
    • F. Sa̧czewski, A. Innocenti, Z. Brzozowski, J. Sławiń ski, E. Pomarnacka, A. Kornicka, A. Scozzafava, and C.T. Supuran Carbonic anhydrase inhibitors. Selective inhibition of human tumor-associated isozymes IX and XII and cytosolic isozymes I and II with some substituted-2-mercapto- benzenesulfonamides J. Enzyme Inhib. Med. Chem. 21 2006 563 568 (Pubitemid 44768466)
    • (2006) Journal of Enzyme Inhibition and Medicinal Chemistry , vol.21 , Issue.5 , pp. 563-568
    • Saczewski, F.1    Innocenti, A.2    Brzozowski, Z.3    Slawilski, J.4    Pomarnacka, E.5    Kornicka, A.6    Scozzafava, A.7    Supuran, C.T.8
  • 42
    • 41649093536 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Inhibition of human cytosolic isozymes I and II and tumor-associated isozymes IX and XII with S-substituted 4-chloro-2-mercapto-5-methyl-benzenesulfonamides
    • DOI 10.1016/j.bmc.2008.01.034, PII S0968089608000539
    • F. Sa̧czewski, A. Innocenti, J. Sławiński, A. Kornicka, Z. Brzozowski, E. Pomarnacka, A. Scozzafava, C. Temperini, and C.T. Supuran Carbonic anhydrase inhibitors: inhibition of human cytosolic isozymes I and II and tumor-associated isozymes IX and XII with S-substituted 4-chloro-2-mercapto-5-methyl-benzenesulfonamides Bioorg. Med. Chem. 16 2008 3933 3940 (Pubitemid 351484021)
    • (2008) Bioorganic and Medicinal Chemistry , vol.16 , Issue.7 , pp. 3933-3940
    • Saczewski, F.1    Innocenti, A.2    Slawinski, J.3    Kornicka, A.4    Brzozowski, Z.5    Pomarnacka, E.6    Scozzafava, A.7    Temperini, C.8    Supuran, C.T.9
  • 44
    • 0005918224 scopus 로고
    • Pochodne kwasu 4-chloro-5-sulfoamoilobenzoesowego. 8. Synteza i właściwości diuretyczne pochodnych pirazolo [3,2-b] chinazoliny i 1-benzoilopirazolu
    • E. Pomarnacka, S. Angielski, and A. Hoppe Pochodne kwasu 4-chloro-5-sulfoamoilobenzoesowego. 8. Synteza i właściwoś ci diuretyczne pochodnych pirazolo [3,2-b] chinazoliny i 1-benzoilopirazolu Acta Pol. Pharm. 41 1984 141 151
    • (1984) Acta Pol. Pharm. , vol.41 , pp. 141-151
    • Pomarnacka, E.1    Angielski, S.2    Hoppe, A.3
  • 45
    • 84861349310 scopus 로고    scopus 로고
    • Synthesis and in vitro activity of novel 2-(benzylthio)-4-chloro-5-(1,3, 4-oxadiazol-2-yl)benzenesulfonamide derivatives
    • K. Brozewicz, and J. Sławiński Synthesis and in vitro activity of novel 2-(benzylthio)-4-chloro-5-(1,3,4-oxadiazol-2-yl) benzenesulfonamide derivatives Monatsh. Chem. 143 2012 975 984
    • (2012) Monatsh. Chem. , vol.143 , pp. 975-984
    • Brozewicz, K.1    Sławiński, J.2
  • 46
    • 0015239422 scopus 로고
    • The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C
    • R.G. Khalifah The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C J. Biol. Med. 246 1971 2561 2573
    • (1971) J. Biol. Med. , vol.246 , pp. 2561-2573
    • Khalifah, R.G.1
  • 47
    • 1842628633 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX
    • DOI 10.1021/jm031079w
    • J.R. Casey, P.E. Morgan, D. Vullo, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX J. Med. Chem. 47 2004 2337 2347 (Pubitemid 38478857)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.9 , 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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