{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,23]],"date-time":"2026-06-23T23:53:17Z","timestamp":1782258797707,"version":"3.54.5"},"reference-count":66,"publisher":"American Chemical Society (ACS)","issue":"2","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Med. Chem."],"published-print":{"date-parts":[[2000,1,1]]},"DOI":"10.1021\/jm990479+","type":"journal-article","created":{"date-parts":[[2002,7,26]],"date-time":"2002-07-26T06:06:54Z","timestamp":1027663614000},"page":"292-300","source":"Crossref","is-referenced-by-count":202,"title":["Carbonic Anhydrase Inhibitors:\u2009 Synthesis of Membrane-Impermeant Low Molecular Weight Sulfonamides Possessing in Vivo Selectivity for the Membrane-Bound versus Cytosolic Isozymes"],"prefix":"10.1021","volume":"43","author":[{"given":"Andrea","family":"Scozzafava","sequence":"first","affiliation":[{"name":"Laboratorio di Chimica Inorganica e Bioinorganica, Universit\u00e0 degli Studi, Via Gino Capponi 7, I-50121 Florence, Italy, and Department of Chemistry, Faculty of Biotechnologies, University of Agricultural Sciences and Veterinary Medicine, B-dul Marasti nr. 59, 71331 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fabrizio","family":"Briganti","sequence":"additional","affiliation":[{"name":"Laboratorio di Chimica Inorganica e Bioinorganica, Universit\u00e0 degli Studi, Via Gino Capponi 7, I-50121 Florence, Italy, and Department of Chemistry, Faculty of Biotechnologies, University of Agricultural Sciences and Veterinary Medicine, B-dul Marasti nr. 59, 71331 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marc A.","family":"Ilies","sequence":"additional","affiliation":[{"name":"Laboratorio di Chimica Inorganica e Bioinorganica, Universit\u00e0 degli Studi, Via Gino Capponi 7, I-50121 Florence, Italy, and Department of Chemistry, Faculty of Biotechnologies, University of Agricultural Sciences and Veterinary Medicine, B-dul Marasti nr. 59, 71331 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudiu T.","family":"Supuran","sequence":"additional","affiliation":[{"name":"Laboratorio di Chimica Inorganica e Bioinorganica, Universit\u00e0 degli Studi, Via Gino Capponi 7, I-50121 Florence, Italy, and Department of Chemistry, Faculty of Biotechnologies, University of Agricultural Sciences and Veterinary Medicine, B-dul Marasti nr. 59, 71331 Bucharest, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[1999,12,29]]},"reference":[{"key":"jm9904791b00001\/jm9904791b00001_1","unstructured":"This paper is part 83 of the series. Preceding part:\u2009 Renzi, G.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Part 82. Topical sulfonamide antiglaucoma agents incorporating secondary amine moieties.Bioorg.Med. Chem. Lett.1999, in press."},{"key":"jm9904791b00002\/jm9904791b00002_1","volume-title":"Carbonic Anhydrase \u2212 New Horizons","author":"Hewett-Emmett D.","year":"1999"},{"key":"jm9904791b00002\/jm9904791b00002_2","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1006\/mpev.1996.0006","volume":"5","author":"Hewett-Emmett D.","year":"1996","journal-title":"Mol. Phyl. Evol."},{"key":"jm9904791b00003\/jm9904791b00003_1","first-page":"111","volume-title":"Carbonic Anhydrase and Modulation of Physiologic and Pathologic Processes in the Organism","author":"Supuran C. T.","year":"1994"},{"key":"jm9904791b00004\/jm9904791b00004_1","doi-asserted-by":"crossref","first-page":"276","DOI":"10.1002\/ddr.430100407","volume":"10","author":"Maren T. H.","year":"1987","journal-title":"Drug Dev. Res."},{"key":"jm9904791b00004\/jm9904791b00004_2","doi-asserted-by":"crossref","first-page":"782","DOI":"10.1152\/physrev.1967.47.4.595","volume":"47","author":"Maren T. H.","year":"1967","journal-title":"Physiol. Rev."},{"key":"jm9904791b00005\/jm9904791b00005_1","volume-title":"Carbonic Anhydrase \u2212 New Horizons","author":"Chegwidden W. R.","year":"1999"},{"key":"jm9904791b00006\/jm9904791b00006_1","first-page":"1734","volume-title":"Aparelho Digestivo","author":"Puscas I.","year":"1996"},{"key":"jm9904791b00007\/jm9904791b00007_1","first-page":"562","volume":"13","author":"Beyer K. H.","year":"1961","journal-title":"Pharmacol. Rev."},{"key":"jm9904791b00008\/jm9904791b00008_1","doi-asserted-by":"crossref","first-page":"14747","DOI":"10.1074\/jbc.270.24.14742","volume":"270","author":"Cabiscol E.","year":"1995","journal-title":"J. Biol. Chem."},{"key":"jm9904791b00009\/jm9904791b00009_1","doi-asserted-by":"crossref","first-page":"24623","DOI":"10.1074\/jbc.273.38.24620","volume":"273","author":"Parkkila A. K.","year":"1998","journal-title":"J. Biol. Chem."},{"key":"jm9904791b00010\/jm9904791b00010_1","first-page":"2888","volume":"9","author":"Pastorek J.","year":"1994","journal-title":"Oncogene"},{"key":"jm9904791b00010\/jm9904791b00010_2","doi-asserted-by":"crossref","first-page":"408","DOI":"10.1053\/gast.1997.v112.pm9024293","volume":"112","author":"Pastorekova S.","year":"1997","journal-title":"Gastroenterology"},{"key":"jm9904791b00011\/jm9904791b00011_1","volume-title":"\u201cacatalytic","author":"Lovejoy D. A.","year":"1998"},{"key":"jm9904791b00012\/jm9904791b00012_1","first-page":"298","volume":"1384","author":"Bergenhem N. C. H.","year":"1998","journal-title":"Biochim. Biophys. Acta"},{"key":"jm9904791b00013\/jm9904791b00013_1","first-page":"7613","volume":"95","author":"Tureci O.","year":"1998","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"jm9904791b00014\/jm9904791b00014_1","first-page":"15705","volume":"274","author":"Mori K.","year":"1999","journal-title":"J. Biol. Chem."},{"key":"jm9904791b00015\/jm9904791b00015_1","doi-asserted-by":"crossref","first-page":"2678","DOI":"10.1021\/bi962663s","volume":"36","author":"Baird T. T.","year":"1997","journal-title":"Biochemistry"},{"key":"jm9904791b00016\/jm9904791b00016_1","doi-asserted-by":"crossref","first-page":"12601","DOI":"10.1073\/pnas.95.21.12596","volume":"95","author":"Ivanov S. V.","year":"1998","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"jm9904791b00017\/jm9904791b00017_1","first-page":"2650","volume":"42","author":"Scozzafava A.","year":"1999","journal-title":"J. Med. Chem."},{"key":"jm9904791b00018\/jm9904791b00018_1","doi-asserted-by":"crossref","first-page":"2406","DOI":"10.1016\/S0968-0896(99)00190-X","volume":"7","author":"Borras J.","year":"1999","journal-title":"Bioorg. Med. Chem."},{"key":"jm9904791b00019\/jm9904791b00019_1","first-page":"3700","volume":"42","author":"Scozzafava A.","year":"1999","journal-title":"J. Med. Chem."},{"key":"jm9904791b00020\/jm9904791b00020_1","doi-asserted-by":"crossref","first-page":"328","DOI":"10.1016\/S0928-0987(99)00022-6","volume":"8","author":"Supuran C. T.","year":"1999","journal-title":"Eur. J. Pharm. Sci."},{"key":"jm9904791b00021\/jm9904791b00021_1","doi-asserted-by":"crossref","first-page":"595","DOI":"10.1016\/S0223-5234(98)80018-4","volume":"33","author":"Supuran C. T.","year":"1998","journal-title":"Eur. J. Med. Chem."},{"key":"jm9904791b00022\/jm9904791b00022_1","first-page":"846","volume":"31","author":"Supuran C. T.","year":"1996","journal-title":"Eur. J. Med. Chem."},{"key":"jm9904791b00023\/jm9904791b00023_1","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1002\/jps.2600810726","volume":"81","author":"Supuran C. T.","year":"1992","journal-title":"J. Pharm. Sci."},{"key":"jm9904791b00024\/jm9904791b00024_1","first-page":"360","volume-title":"Advances in Heterocyclic Chemistry","author":"Balaban A. T.","year":"1982"},{"key":"jm9904791b00024\/jm9904791b00024_2","first-page":"1528","volume":"25","author":"Dinculescu A.","year":"1980","journal-title":"Rev. Roum. Chim."},{"key":"jm9904791b00024\/jm9904791b00024_3","first-page":"34","author":"Toma C.","year":"1966","journal-title":"Tetrahedron"},{"key":"jm9904791b00025\/jm9904791b00025_1","first-page":"671","volume":"37","author":"Supuran C. T.","year":"1994","journal-title":"Heterocycles"},{"key":"jm9904791b00026\/jm9904791b00026_1","first-page":"2105","volume":"37","author":"Jain A.","year":"1994","journal-title":"J. Med. Chem."},{"key":"jm9904791b00027\/jm9904791b00027_1","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1021\/jm00053a016","volume":"36","author":"Avila L. Z.","year":"1993","journal-title":"J. Med. Chem."},{"key":"jm9904791b00028\/jm9904791b00028_1","first-page":"448","volume":"31","author":"Supuran C. T.","year":"1996","journal-title":"Eur. J. Med. Chem."},{"key":"jm9904791b00029\/jm9904791b00029_1","first-page":"190","volume":"12","author":"Supuran C. T.","year":"1997","journal-title":"J. Enzyme Inhib."},{"key":"jm9904791b00030\/jm9904791b00030_1","first-page":"104","volume":"280","author":"Maren T. H.","year":"1997","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"jm9904791b00030\/jm9904791b00030_2","first-page":"F147","volume":"274","author":"Tsuruoka S.","year":"1998","journal-title":"Am. J. Physiol."},{"key":"jm9904791b00031\/jm9904791b00031_1","doi-asserted-by":"crossref","first-page":"F449","DOI":"10.1152\/ajpcell.1983.245.5.C449","volume":"245","author":"Lucci M. S.","year":"1983","journal-title":"Am. J. Physiol."},{"key":"jm9904791b00031\/jm9904791b00031_2","first-page":"607","volume":"218","author":"Tinker J. P.","year":"1981","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"jm9904791b00032\/jm9904791b00032_1","doi-asserted-by":"crossref","first-page":"1856","DOI":"10.1152\/jappl.1986.61.5.1849","volume":"61","author":"Heming T. A.","year":"1986","journal-title":"J. Appl. Physiol."},{"key":"jm9904791b00033\/jm9904791b00033_1","doi-asserted-by":"crossref","first-page":"538","DOI":"10.1146\/annurev.ph.58.030196.002515","volume":"58","author":"Henry R. P","year":"1996","journal-title":"Annu. Rev. Physiol."},{"key":"jm9904791b00033\/jm9904791b00033_2","first-page":"R1761","volume":"272","author":"Henry R. P.","year":"1997","journal-title":"Am. J. Physiol."},{"key":"jm9904791b00034\/jm9904791b00034_1","doi-asserted-by":"crossref","first-page":"696","DOI":"10.1016\/0223-5234(96)88286-9","volume":"30","author":"Supuran C. T.","year":"1995","journal-title":"Eur. J. Med. Chem."},{"key":"jm9904791b00035\/jm9904791b00035_1","first-page":"378","volume-title":"Carbonic Anhydrase \u2212 From Biochemistry and Genetics to Physiology and Clinical Medicine","author":"Wistrand P. J.","year":"1991"},{"key":"jm9904791b00036\/jm9904791b00036_1","first-page":"115","volume-title":"Orphan Drugs","author":"Maren T. H.","year":"1982"},{"key":"jm9904791b00037\/jm9904791b00037_1","first-page":"231","volume-title":"Carbonic Anhydrase \u2212 From Biochemistry and Genetics to Physiology and Clinical Medicine","author":"Sly W. S.","year":"1991"},{"key":"jm9904791b00038\/jm9904791b00038_1","first-page":"149","volume-title":"The Pharmacological Basis of Therapeutics","author":"Taylor P.","year":"1990","edition":"8"},{"key":"jm9904791b00039\/jm9904791b00039_1","first-page":"166","volume-title":"The Pharmacological Basis of Therapeutics","author":"Brown J. H.","year":"1990","edition":"8"},{"key":"jm9904791b00040\/jm9904791b00040_1","first-page":"186","volume-title":"The Pharmacological Basis of Therapeutics","author":"Taylor P.","year":"1990","edition":"8"},{"key":"jm9904791b00041\/jm9904791b00041_1","first-page":"99","volume":"71","author":"Crippa G. B.","year":"1941","journal-title":"Gazz. Chim. Ital."},{"key":"jm9904791b00042\/jm9904791b00042_1","first-page":"282","volume":"78","author":"Cingolani E","year":"1948","journal-title":"Gazz. Chim. Ital."},{"key":"jm9904791b00043\/jm9904791b00043_1","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1515\/MGMC.1997.20.3.151","volume":"20","author":"Jitianu A.","year":"1997","journal-title":"Main Group Met. Chem."},{"key":"jm9904791b00044\/jm9904791b00044_1","volume":"14","author":"Barboiu M.","year":"1999","journal-title":"J. Enzyme Inhib."},{"key":"jm9904791b00045\/jm9904791b00045_1","first-page":"751","volume":"33","author":"Supuran C. T.","year":"1998","journal-title":"Eur. J. Med. Chem."},{"key":"jm9904791b00046\/jm9904791b00046_1","first-page":"160","volume":"74","author":"Eller M. G.","year":"1985","journal-title":"J. Pharm. Sci."},{"key":"jm9904791b00047\/jm9904791b00047_1","first-page":"13","volume-title":"Carbonic anhydrase \u2212 From biochemistry and genetics to physiology and clinical medicine","author":"Lindskog S.","year":"1991"},{"key":"jm9904791b00048\/jm9904791b00048_1","doi-asserted-by":"crossref","first-page":"357","DOI":"10.1111\/j.1432-1033.1990.tb15582.x","volume":"190","author":"Behravan G.","year":"1990","journal-title":"Eur. J. Biochem."},{"key":"jm9904791b00049\/jm9904791b00049_1","first-page":"2247","volume":"16","author":"Khalifah R. G.","year":"1977","journal-title":"Biochemistry"},{"key":"jm9904791b00050\/jm9904791b00050_1","first-page":"2508","volume":"70","author":"Lindskog S.","year":"1964","journal-title":"Proc. Natl. Acad Sci. U.S.A."},{"key":"jm9904791b00051\/jm9904791b00051_1","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1111\/j.1432-1033.1975.tb02449.x","volume":"59","author":"Steiner H.","year":"1975","journal-title":"Eur. J. Biochem."},{"key":"jm9904791b00052\/jm9904791b00052_1","first-page":"906","volume":"44","author":"Maren T. H.","year":"1993","journal-title":"Mol. Pharmacol."},{"key":"jm9904791b00053\/jm9904791b00053_1","first-page":"678","volume":"6","author":"Pocker Y.","year":"1967","journal-title":"Biochemistry"},{"key":"jm9904791b00054\/jm9904791b00054_1","doi-asserted-by":"crossref","first-page":"731","DOI":"10.1002\/jps.2600660533","volume":"66","author":"Wallace S. M.","year":"1977","journal-title":"J. Pharm. Sci."},{"key":"jm9904791b00055\/jm9904791b00055_1","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1002\/bmc.1130070305","volume":"7","author":"Gomaa Z. S","year":"1993","journal-title":"Biomed. Chromatogr."},{"key":"jm9904791b00056\/jm9904791b00056_1","first-page":"1027","volume":"16","author":"Iyer G. R.","year":"1998","journal-title":"J. Pharm. Biomed. Anal."},{"key":"jm9904791b00057\/jm9904791b00057_1","first-page":"701","volume":"61","author":"Abdine H.","year":"1978","journal-title":"J. Assoc. Off. Anal. Chem."},{"key":"jm9904791b00058\/jm9904791b00058_1","first-page":"245","volume":"22","author":"Forrester R. L.","year":"1976","journal-title":"Clin. Chem."}],"container-title":["Journal of Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jm990479%2B","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,2,3]],"date-time":"2022-02-03T04:11:06Z","timestamp":1643861466000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jm990479%2B"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1999,12,29]]},"references-count":66,"aliases":["10.1021\/jm990479","10.1021\/jm990479","10.1021\/jm990479","10.1021\/jm990479"],"journal-issue":{"issue":"2","published-print":{"date-parts":[[2000,1,1]]}},"alternative-id":["10.1021\/jm990479+"],"URL":"https:\/\/doi.org\/10.1021\/jm990479+","relation":{},"ISSN":["0022-2623","1520-4804"],"issn-type":[{"value":"0022-2623","type":"print"},{"value":"1520-4804","type":"electronic"}],"subject":[],"published":{"date-parts":[[1999,12,29]]}}}