{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,14]],"date-time":"2026-01-14T04:30:58Z","timestamp":1768365058836,"version":"3.49.0"},"reference-count":92,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2016,11,18]],"date-time":"2016-11-18T00:00:00Z","timestamp":1479427200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2016,12]]},"abstract":"<jats:sec><jats:label\/><jats:p>Carbonic anhydrase (CA, EC 4.2.1.1) is a member of the metalloenzyme family. It catalyzes the rapid conversion of carbon dioxide (CO<jats:sub>2<\/jats:sub>) and water to bicarbonate (HCO<jats:sub>3<\/jats:sub><jats:sup>\u2212<\/jats:sup>) and protons (H<jats:sup>+<\/jats:sup>) and also plays an important role in biochemical and physiological processes. In this study, a number of novel 2\u2010(4\u2010(aryl)thiazole\u20102\u2010yl)\u20103a,4,7,7a\u2010tetrahydro\u20101<jats:italic>H<\/jats:italic>\u20104,7\u2010methanoisoindole\u20101,3(2<jats:italic>H<\/jats:italic>)\u2010dione derivatives were synthesized and evaluated for their inhibitory characteristics against the human CA isoenzymes I and II (hCA I and hCA II). The structures of the new molecules <jats:bold>8a\u2013i<\/jats:bold> were confirmed by means of IR, <jats:sup>1<\/jats:sup>H NMR, <jats:sup>13<\/jats:sup>C NMR, and elemental analysis. These compounds exhibited excellent inhibitory effects, in the low nanomolar range, with <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values in the range of 27.07\u201337.80\u2009nM against hCA I and in the range of 11.80\u201325.81\u2009nM against hCA II. Our findings suggest that the new isoindolylthiazole derivatives have superior inhibitory effect over acetazolamide (AZA), which is used as clinical CA inhibitor with <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values of 34.50 and 28.93\u2009nM against the hCA I and hCA II isoenzymes, respectively.<\/jats:p><\/jats:sec>","DOI":"10.1002\/ardp.201600092","type":"journal-article","created":{"date-parts":[[2016,11,18]],"date-time":"2016-11-18T13:12:44Z","timestamp":1479474764000},"page":"955-963","source":"Crossref","is-referenced-by-count":44,"title":["Synthesis and Carbonic Anhydrase Inhibition of Novel 2\u2010(4\u2010(Aryl)thiazole\u20102\u2010yl)\u20103a,4,7,7a\u2010tetrahydro\u20101<i>H<\/i>\u20104,7\u2010methanoisoindole\u20101,3(2<i>H<\/i>)\u2010dione Derivatives"],"prefix":"10.1002","volume":"349","author":[{"given":"Umit M.","family":"Kocyigit","sequence":"first","affiliation":[{"name":"Vocational School of Health Services Cumhuriyet University Sivas Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Osman Nuri","family":"Aslan","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Arts and Sciences Gaziosmanpasa University Tokat Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ilhami","family":"Gulcin","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Science Atat\u00fcrk University Erzurum Turkey"},{"name":"Department of Zoology College of Science King Saud University Riyadh Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yusuf","family":"Temel","sequence":"additional","affiliation":[{"name":"Department of Solhan School of Health Services Bingol University Bingol Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mustafa","family":"Ceylan","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Arts and Sciences Gaziosmanpasa University Tokat Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2016,11,18]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1590\/S0100-40422003000200016"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02980121"},{"key":"e_1_2_7_4_1","doi-asserted-by":"crossref","first-page":"1660","DOI":"10.24297\/jac.v8i2.5570","volume":"8","author":"Lamie P. F.","year":"2005","journal-title":"J. Adv. Chem"},{"key":"e_1_2_7_4_2","first-page":"98","volume":"5","author":"Amin K. M.","year":"2013","journal-title":"Pharm. Chem"},{"key":"e_1_2_7_4_3","first-page":"353","volume":"6","author":"Pawar S.","year":"2014","journal-title":"Int. J. Pharm. Sci"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)10116-2"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm9905817"},{"key":"e_1_2_7_7_1","first-page":"3067","volume":"20","author":"Wang J. J.","year":"2000","journal-title":"Anticancer Res"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0223-5234(01)01254-5"},{"key":"e_1_2_7_9_1","first-page":"35","volume":"2","author":"Hassanzadeh F.","year":"2007","journal-title":"Res. Pharm. Sci"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.109.2841.588"},{"key":"e_1_2_7_11_1","first-page":"193","volume":"13","author":"Ali I. A. I.","year":"2009","journal-title":"Arkivoc"},{"key":"e_1_2_7_12_1","first-page":"315","volume":"12","author":"Kant P.","year":"2003","journal-title":"Ind. J. Heterocycl. Chem"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/0015-6264(75)90082-6"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00044-016-1580-4"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/js980172i"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00362a014"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00092a006"},{"key":"e_1_2_7_18_1","first-page":"134","volume":"6","author":"Nevagi R. J.","year":"2014","journal-title":"Pharm. Lett"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00163a051"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0223-5234(02)01447-2"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00025a010"},{"key":"e_1_2_7_22_1","first-page":"223","volume":"39","author":"Rasina L. N.","year":"1999","journal-title":"Radioekologiya"},{"key":"e_1_2_7_23_1","first-page":"162","volume":"30","author":"Rasina L. N.","year":"1990","journal-title":"Radiobiologiya"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1093\/jac\/dki084"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2009.11.008"},{"key":"e_1_2_7_26_1","first-page":"61","volume":"1","author":"Supuran C. T.","year":"2001","journal-title":"Curr. Med. Chem"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm501573b"},{"key":"e_1_2_7_26_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.12.054"},{"key":"e_1_2_7_26_4","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201500035"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574-6976.2000.tb00546.x"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2015.04.019"},{"key":"e_1_2_7_27_3","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2014.999236"},{"key":"e_1_2_7_27_4","first-page":"408","volume":"13","author":"G\u00fcl\u00e7in \u0130.","year":"2013","journal-title":"Mini Rev. Med. Chem"},{"key":"e_1_2_7_28_1","first-page":"375","volume":"64","author":"Sly S. W.","year":"1995","journal-title":"Annu. Rev"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2014.956310"},{"key":"e_1_2_7_28_3","doi-asserted-by":"publisher","DOI":"10.3390\/molecules190710103"},{"key":"e_1_2_7_28_4","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2014.928704"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0050860"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2014.08.015"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.3390\/ijms17101736"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201400257"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2014.07.009"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature06636"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.3906\/kim-1403-5"},{"key":"e_1_2_7_32_3","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1135914"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbrc.2014.05.100"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2016.04.002"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.2174\/138161208783877947"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201300349"},{"key":"e_1_2_7_35_1","first-page":"343","author":"Chegwidden W. R.","year":"2000","journal-title":"New Horiz"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2012.750311"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.2174\/092986712799034824"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2012.763163"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2467"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201300273"},{"key":"e_1_2_7_37_3","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201600047"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2012.672983"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.etap.2016.04.011"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1517\/17460441.2013.795145"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2012.672983"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/hc.20182"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397910802691874"},{"key":"e_1_2_7_40_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2005.01.006"},{"key":"e_1_2_7_40_4","doi-asserted-by":"publisher","DOI":"10.1080\/10426500802715163"},{"key":"e_1_2_7_40_5","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2007.10.029"},{"key":"e_1_2_7_41_1","first-page":"102","volume":"6","author":"Ceylan M.","year":"2013","journal-title":"Org. Commun"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1747-0285.2010.00965.x"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201300228"},{"key":"e_1_2_7_42_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2012.08.072"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1747-0285.2011.01104.x"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2013.03.077"},{"key":"e_1_2_7_43_3","doi-asserted-by":"publisher","DOI":"10.1556\/AVet.52.2004.4.4"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756360310001656736"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2013.01.019"},{"key":"e_1_2_7_44_3","doi-asserted-by":"publisher","DOI":"10.1080\/1475636040001704461"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1248\/bpb.27.613"},{"key":"e_1_2_7_45_2","first-page":"841","volume":"29","author":"Hisar O.","year":"2005","journal-title":"Turk. J. Vet. Anim. Sci"},{"key":"e_1_2_7_45_3","doi-asserted-by":"publisher","DOI":"10.1248\/bpb.30.2257"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)95800-X"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1080\/14756360701474780"},{"key":"e_1_2_7_46_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2009.01.067"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01318a036"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2009.07.019"},{"key":"e_1_2_7_47_3","doi-asserted-by":"publisher","DOI":"10.1080\/10942912.2015.1012725"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/0003-2697(76)90527-3"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2012.670807"},{"key":"e_1_2_7_48_3","doi-asserted-by":"crossref","first-page":"1182","DOI":"10.1080\/10942912.2010.511924","volume":"15","author":"\u015ei\u015fecio\u011flu M.","year":"2012","journal-title":"Int. J. Food Propert"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1038\/227680a0"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1080\/1475636032000141890"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejphar.2011.07.032"},{"key":"e_1_2_7_50_3","first-page":"1351","volume":"5","author":"\u015ei\u015fecio\u011flu M.","year":"2010","journal-title":"Sci. Res. Essays"}],"container-title":["Archiv der Pharmazie"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fardp.201600092","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fardp.201600092","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ardp.201600092","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,5]],"date-time":"2023-10-05T23:36:30Z","timestamp":1696548990000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/ardp.201600092"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,11,18]]},"references-count":92,"journal-issue":{"issue":"12","published-print":{"date-parts":[[2016,12]]}},"alternative-id":["10.1002\/ardp.201600092"],"URL":"https:\/\/doi.org\/10.1002\/ardp.201600092","archive":["Portico"],"relation":{},"ISSN":["0365-6233","1521-4184"],"issn-type":[{"value":"0365-6233","type":"print"},{"value":"1521-4184","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,11,18]]}}}