{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,12]],"date-time":"2026-01-12T22:21:42Z","timestamp":1768256502571,"version":"3.49.0"},"reference-count":86,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2015,12,29]],"date-time":"2015-12-29T00:00:00Z","timestamp":1451347200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100004951","name":"Atat\u00fcrk \u00dcniversitesi","doi-asserted-by":"publisher","award":["2012\/154"],"award-info":[{"award-number":["2012\/154"]}],"id":[{"id":"10.13039\/501100004951","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002383","name":"King Saud University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100002383","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chem Biol Drug Des"],"published-print":{"date-parts":[[2016,4]]},"abstract":"<jats:p>Rearrangement of 1,6\u2010bis(3,4\u2010dimethoxyphenyl)hexane\u20101,6\u2010dione (<jats:bold>8<\/jats:bold>) gave two isomeric products having cyclopentene moiety. Starting from the major product (3,4\u2010dimethoxyphenyl)[2\u2010(3,4\u2010dimethoxyphenyl)cyclopent\u20101\u2010en\u20101\u2010yl]methanone (<jats:bold>11<\/jats:bold>), eight new compounds (<jats:bold>16\u201323)<\/jats:bold> were obtained by the reactions such as reduction (by catalytic hydrogenation and Na<jats:styled-content style=\"fixed-case\">BH<\/jats:styled-content><jats:sub>4<\/jats:sub>), nitration, 1,4\u2010addition, bromination, and esterification reactions. Carbonic anhydrases (<jats:styled-content style=\"fixed-case\">CA<\/jats:styled-content>, E.C.4.2.1.1) are ubiquitous metalloenzymes present in almost all living organism that catalyze a simple reaction, the conversion of carbon dioxide (<jats:styled-content style=\"fixed-case\">CO<\/jats:styled-content><jats:sub>2<\/jats:sub>) and water (H<jats:sub>2<\/jats:sub>O) to bicarbonate ion (<jats:styled-content style=\"fixed-case\">HCO<\/jats:styled-content><jats:sub>3<\/jats:sub><jats:sup>\u2212<\/jats:sup>) and a proton (H<jats:sup>+<\/jats:sup>). <jats:styled-content style=\"fixed-case\">CA<\/jats:styled-content> isoenzymes I and <jats:styled-content style=\"fixed-case\">II<\/jats:styled-content> (<jats:styled-content style=\"fixed-case\">hCA<\/jats:styled-content> I and <jats:styled-content style=\"fixed-case\">II<\/jats:styled-content>) inhibition effects of synthesized eleven new and four known compounds (<jats:bold>8\u201313<\/jats:bold> and <jats:bold>15\u201323<\/jats:bold>) were investigated. Inhibition studies of the <jats:styled-content style=\"fixed-case\">hCA<\/jats:styled-content> I and <jats:styled-content style=\"fixed-case\">II<\/jats:styled-content> with 4\u2010[2\u2010(3,4\u2010dimethoxybenzyl)cyclopentyl]\u20101,2\u2010dimethoxybenzene derivatives revealed that they possess effective inhibitory potency. Cytosolic <jats:styled-content style=\"fixed-case\">hCA<\/jats:styled-content> I and <jats:styled-content style=\"fixed-case\">II<\/jats:styled-content> isoenzymes were potently inhibited by new synthesized 4\u2010[2\u2010(3,4\u2010dimethoxybenzyl)cyclopentyl]\u20101,2\u2010dimethoxybenzene derivatives with K<jats:sub>i<\/jats:sub>s in the range of 313.16\u20131537.00 n<jats:sc>m<\/jats:sc> against <jats:styled-content style=\"fixed-case\">hCA<\/jats:styled-content> I and in the range of 228.31\u20131927.31 <jats:styled-content style=\"fixed-case\">n<\/jats:styled-content><jats:sc>m<\/jats:sc> against <jats:styled-content style=\"fixed-case\">hCA II<\/jats:styled-content>, respectively.<\/jats:p>","DOI":"10.1111\/cbdd.12695","type":"journal-article","created":{"date-parts":[[2015,12,9]],"date-time":"2015-12-09T05:36:39Z","timestamp":1449639399000},"page":"594-607","source":"Crossref","is-referenced-by-count":49,"title":["Synthesis of 4\u2010[2\u2010(3,4\u2010dimethoxybenzyl)cyclopentyl]\u20101,2\u2010dimethoxybenzene Derivatives and Evaluations of Their Carbonic Anhydrase Isoenzymes Inhibitory Effects"],"prefix":"10.1111","volume":"87","author":[{"given":"Tekin","family":"Artun\u00e7","sequence":"first","affiliation":[{"name":"Department of Chemistry Faculty of Science Atat\u00fcrk University Erzurum Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yasin","family":"\u00c7etinkaya","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Science Atat\u00fcrk University Erzurum Turkey"},{"name":"Department of Food Technology Oltu Vocational School Atat\u00fcrk University Oltu\u2010Erzurum Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"H\u00fclya","family":"G\u00f6\u00e7er","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Science Atat\u00fcrk University Erzurum Turkey"},{"name":"Faculty of Sciences and Letters A\u01e7ri Ibrahim Cecen University A\u01e7ri Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"\u0130lhami","family":"G\u00fcl\u00e7in","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":"Abdullah","family":"Menzek","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Science Atat\u00fcrk University Erzurum Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ertan","family":"\u015eahin","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Science Atat\u00fcrk University Erzurum Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Claudiu T.","family":"Supuran","sequence":"additional","affiliation":[{"name":"Dipartimento NEUROFARBA Sezione di Scienze Farmaceutiche Universit\u00e0 degli Studi di Firenze Via Ugo Schiff 6 Sesto Fiorentino (Firenze) I\u201050019 Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2015,12,29]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200101)2001:1<93::AID-EJOC93>3.0.CO;2-X"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2009.03.009"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo5006137"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2005.07.012"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm3004009"},{"key":"e_1_2_8_7_1","first-page":"75","article-title":"First and short syntheses of biologically active, naturally occurring brominated mono\u2010and dibenzyl phenols","author":"Balayd\u0131n H.T.","year":"2009","journal-title":"Arkivoc"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200900300"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.03.033"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756360903514164"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2012.05.025"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2011.12.069"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201100272"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/np040199j"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/np020528c"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201300054"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2012.670807"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2012.715287"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501573b"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1248\/bpb.27.613"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.4155\/fmc.11.69"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2013.03.077"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2012.672983"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1517\/13543776.10.5.575"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756360310001656736"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1080\/1475636040001704461"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2467"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2007.04.020"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.3389\/fphar.2011.00034"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2015.02.045"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr200176r"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1233692"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1042\/BJ20051102"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tips.2006.09.002"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1248\/bpb.30.2257"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.2174\/156802607780636753"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2011.645539"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2011.650168"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2011.649269"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm300529u"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2013.773994"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201310709"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.10.041"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756360701474780"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.04.007"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2010.01.076"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2012.05.037"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2013.787422"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2014.07.009"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules190710103"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.3906\/kim-1403-5"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501798g"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201300273"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2013.02.026"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2014.01.048"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1517\/13543776.2013.778246"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2004.07.087"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2005.04.056"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2011.04.005"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1517\/13543776.16.12.1627"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2012.763163"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2013.864652"},{"key":"e_1_2_8_63_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.01.031"},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2013.10.081"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2013.08.011"},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2014.03.023"},{"key":"e_1_2_8_67_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2014.02.023"},{"key":"e_1_2_8_68_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201300349"},{"key":"e_1_2_8_69_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2013.01.019"},{"key":"e_1_2_8_70_1","first-page":"408","article-title":"Phenolic compounds as antioxidants: carbonic anhydrase isoenzymes inhibitors","volume":"13","author":"G\u00fcl\u00e7in \u0130.","year":"2013","journal-title":"Mini Rev Med Chem"},{"key":"e_1_2_8_71_1","doi-asserted-by":"crossref","first-page":"1182","DOI":"10.1080\/10942912.2010.511924","article-title":"The inhibitory effects of L\u2010adrenaline on lactoperoxidase enzyme (LPO) purified from buffalo milk","volume":"15","author":"\u015ei\u015fecio\u011flu M.","year":"2012","journal-title":"Int J Food Properties"},{"key":"e_1_2_8_72_1","doi-asserted-by":"publisher","DOI":"10.1080\/10942912.2010.513216"},{"key":"e_1_2_8_73_1","doi-asserted-by":"publisher","DOI":"10.1080\/1475636032000141890"},{"key":"e_1_2_8_74_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2012.08.072"},{"key":"e_1_2_8_75_1","doi-asserted-by":"publisher","DOI":"10.1080\/09712119.2005.9706791"},{"key":"e_1_2_8_76_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2009.07.019"},{"key":"e_1_2_8_77_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)95800-X"},{"key":"e_1_2_8_78_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1747-0285.2011.01104.x"},{"key":"e_1_2_8_79_1","doi-asserted-by":"publisher","DOI":"10.1016\/0003-2697(76)90527-3"},{"key":"e_1_2_8_80_1","doi-asserted-by":"publisher","DOI":"10.1248\/bpb.31.2036"},{"key":"e_1_2_8_81_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01318a036"},{"key":"e_1_2_8_82_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2011.05.071"},{"key":"e_1_2_8_83_1","first-page":"1621","article-title":"Silver triflate catalyzed acetylation of alcohols, thiols, and amines","volume":"10","author":"Das R.","year":"2011","journal-title":"Synthesis"},{"key":"e_1_2_8_84_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00706-012-0820-7"},{"key":"e_1_2_8_85_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.01.056"},{"key":"e_1_2_8_86_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2004.01.095"},{"key":"e_1_2_8_87_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2011.05.006"}],"container-title":["Chemical Biology &amp; Drug Design"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1111%2Fcbdd.12695","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1111\/cbdd.12695","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,3]],"date-time":"2023-10-03T08:30:50Z","timestamp":1696321850000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1111\/cbdd.12695"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,12,29]]},"references-count":86,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2016,4]]}},"alternative-id":["10.1111\/cbdd.12695"],"URL":"https:\/\/doi.org\/10.1111\/cbdd.12695","archive":["Portico"],"relation":{},"ISSN":["1747-0277","1747-0285"],"issn-type":[{"value":"1747-0277","type":"print"},{"value":"1747-0285","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,12,29]]}}}