{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,27]],"date-time":"2026-08-27T03:31:06Z","timestamp":1787801466137,"version":"build-2784847793"},"reference-count":48,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2018,8,5]],"date-time":"2018-08-05T00:00:00Z","timestamp":1533427200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2018,9]]},"abstract":"<jats:sec><jats:label\/><jats:p>We report the synthesis of bromoindenoquinolines (<jats:bold>15a<\/jats:bold>\u2013<jats:bold>f<\/jats:bold>) by Friedlander reactions in low yields (13\u201350%) and the conversion of the corresponding phenyl\u2010substituted indenoquinoline derivatives <jats:bold>16<\/jats:bold>\u2013<jats:bold>21<\/jats:bold> in high yields (80\u201396%) by Suzuki coupling reactions. To explore the structure\u2013activity relationship (SAR), their inhibition potentials to inhibit acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase cyctosolic (hCA I and II) enzymes were determined. Monophenyl (<jats:bold>16<\/jats:bold>\u2013<jats:bold>18<\/jats:bold>) indenoquinolines significantly inhibited the AChE and BChE enzymes in ranges of IC<jats:sub>50<\/jats:sub> 37\u201357\u2009nM and 84\u201393\u2009nM, respectively, compared with their starting materials <jats:bold>15a\u2013c<\/jats:bold> and reference compounds (galanthamine and tacrine). On the other hand, these novel arylated indenoquinoline\u2010based derivatives were effective inhibitors of the BChE, hCA I and II, BChE and AChE enzymes with <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values in the range of 37\u2009\u00b1\u20092.04 to 88640\u2009\u00b1\u20091990\u2009nM for AChE, 120.94\u2009\u00b1\u200937.06 to 1150.95\u2009\u00b1\u2009304.48\u2009nM for hCA I, 267.58\u2009\u00b1\u200998.05 to 1568.16\u2009\u00b1\u2009438.67\u2009nM for hCA II, and 84\u2009\u00b1\u20093.86 to 144120\u2009\u00b1\u20092910\u2009nM for BChE. As a result, monophenyl indenoquinolines <jats:bold>16<\/jats:bold>\u2013<jats:bold>18<\/jats:bold> may have promising anti\u2010Alzheimer drug potential and 3,8\u2010dibromoindenoquinoline amine (<jats:bold>15f<\/jats:bold>) can be novel hCA I and hCA II enzyme inhibitors.<\/jats:p><\/jats:sec>","DOI":"10.1002\/ardp.201800167","type":"journal-article","created":{"date-parts":[[2018,8,7]],"date-time":"2018-08-07T07:48:10Z","timestamp":1533628090000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":30,"title":["Synthesis, characterization, and SAR of arylated indenoquinoline\u2010based cholinesterase and carbonic anhydrase inhibitors"],"prefix":"10.1002","volume":"351","author":[{"given":"Makbule","family":"Ekiz","sequence":"first","affiliation":[{"name":"Faculty of Art and Science, Department of Chemistry Sakarya University Serdivan Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ahmet","family":"Tutar","sequence":"additional","affiliation":[{"name":"Faculty of Art and Science, Department of Chemistry Sakarya University Serdivan Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9656-1803","authenticated-orcid":false,"given":"Salih","family":"\u00d6kten","sequence":"additional","affiliation":[{"name":"Faculty of Education, Department of Maths and Science Education K\u0131r\u0131kkale University Kirikkale Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Burcu","family":"B\u00fct\u00fcn","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Department of Pharmaceutical Chemistry Bezmialem Vakif University Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8710-2912","authenticated-orcid":false,"given":"\u00dcmit M.","family":"Ko\u00e7yi\u011fit","sequence":"additional","affiliation":[{"name":"Vocational School of Health Services Cumhuriyet University Sivas Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3171-0633","authenticated-orcid":false,"given":"Parham","family":"Taslimi","sequence":"additional","affiliation":[{"name":"Faculty of Science, Department of Chemistry Ataturk University Erzurum Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"G\u00fcla\u00e7t\u0131","family":"Top\u00e7u","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Department of Pharmacognosy\/Phytochemistry Bezmialem Vakif University Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,8,5]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2016.06.025"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0149-2918(04)90064-1"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2017.01.042"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.2165\/00002512-199710030-00007"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.2165\/00003495-200060050-00008"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1185\/03007990903209332"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11064-007-9490-y"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1017\/S1461145705005833"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/ml300058m"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phymed.2007.02.002"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.21973"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501573b"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.12.054"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201700198"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.21995"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1080\/13813455.2017.1360914"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.3906\/kim-1301-30"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jbiotec.2014.07.359"},{"key":"e_1_2_6_20_1","first-page":"152","volume":"8","author":"\u00d6kten S.","year":"2017","journal-title":"Turk. 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