{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T07:25:52Z","timestamp":1786951552962,"version":"build-2736575974"},"reference-count":64,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2026,7,25]],"date-time":"2026-07-25T00:00:00Z","timestamp":1784937600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,7,25]],"date-time":"2026-07-25T00:00:00Z","timestamp":1784937600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["J Biochem &amp;amp; Molecular Tox"],"published-print":{"date-parts":[[2026,8]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    <jats:italic>N<\/jats:italic>\n                    \u2010heterocyclic carbenes\u00a0(NHCs) are chemical structures called heterocyclic structures that contain one or more nitrogen atoms.\n                    <jats:italic>N<\/jats:italic>\n                    \u2010heterocyclic compounds are the basic building blocks of many drugs and biologically active molecules. One of these compounds is benzimidazolium salts. Herein, we present the synthesis of a series of phenylsulfonylethyl\u2010substituted benzimidazolium salts. These compounds were characterized using NMR (\n                    <jats:sup>1<\/jats:sup>\n                    H\u2010 and\n                    <jats:sup>13<\/jats:sup>\n                    C\u2010) and FTIR spectroscopic techniques. Compound\n                    <jats:bold>1b<\/jats:bold>\n                    exhibits a U\u2010shaped benzimidazolium cation paired with a chloride anion. A hierarchical supramolecular architecture arises from C\u2013H\u22efCl chains, C\u2013H\u22ef\u03c0 layers, and \u03c0\u22ef\u03c0 stacking, demonstrating cooperative non\u2010covalent stabilization of the crystal structure. The synthesized benzimidazolium derivatives exhibited notable inhibitory effect against human carbonic anhydrases (hCA I, hCA II)and acetylcholinesterase (AChE), with several compounds showing markedly lower K\n                    <jats:sub>i<\/jats:sub>\n                    values than the clinical standards. Molecular docking of the NHCs with different receptors showed excellent binding capability with the active site of the target receptors. Moreover, the physicochemical and ADME analysis of the compounds were performed with SwissADME software. Overall examined compounds were found with very good oral bioavailability determined by Lipinski and Verber's rule. The compounds showed Pgp susceptibility with reasonable blood brain barrier permeability.\n                  <\/jats:p>","DOI":"10.1002\/jbt.70893","type":"journal-article","created":{"date-parts":[[2026,7,26]],"date-time":"2026-07-26T06:15:13Z","timestamp":1785046513000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Phenylsulfonylethyl\u2010Substituted Benzimidazolium Salts: Synthesis, Characterization, Crystal Structure, Molecular Docking, and Inhibitory Properties Against Various Enzymes"],"prefix":"10.1002","volume":"40","author":[{"given":"Yetkin","family":"G\u00f6k","sequence":"first","affiliation":[{"name":"Department of Chemistry, Faculty of Arts and Science Inonu University Malatya T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ali","family":"Kazanc\u0131","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Arts and Science Inonu University Malatya T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3216-1098","authenticated-orcid":false,"given":"Yeliz","family":"Demir","sequence":"additional","affiliation":[{"name":"Nihat Delibalta G\u00f6le Vocational High School Ardahan University Ardahan T\u00fcrkiye"},{"name":"Department of Chemistry, Faculty of Science Atat\u00fcrk University Erzurum T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zaroon","family":"Sajid","sequence":"additional","affiliation":[{"name":"Department of Chemistry Mirpur University of Science and Technology (MUST) Mirpur Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Merve","family":"\u0130zmirli","sequence":"additional","affiliation":[{"name":"Department of Engineering Sciences, Faculty of Engineering and Architecture \u0130zmir K\u00e2tip \u00c7elebi University \u0130zmir T\u00fcrkiye"},{"name":"Central Research Laboratories Application and Research Center \u0130zmir K\u00e2tip \u00c7elebi University Izmir T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7386-5107","authenticated-orcid":false,"given":"Muhammad","family":"Haroon","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Miami University Oxford Ohio USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9670-9062","authenticated-orcid":false,"given":"Muhittin","family":"Ayg\u00fcn","sequence":"additional","affiliation":[{"name":"Department of Physics, Faculty of Science Dokuz Eyl\u00fcl University \u0130zmir T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8496-6782","authenticated-orcid":false,"given":"Ayd\u0131n","family":"Akta\u015f","sequence":"additional","affiliation":[{"name":"Vocational School of Health Service Inonu University Malatya T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"\u0130lhami","family":"G\u00fcl\u00e7in","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science Atat\u00fcrk University Erzurum T\u00fcrkiye"},{"name":"Rectorate of Agri Ibrahim Cecen University Agri T\u00fcrkiye"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,7,25]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2020.127802"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.202000422"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.3389\/fcimb.2025.1579916"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2024.140342"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202301362"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2019.127608"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2NJ02026B"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.9734\/IRJPAC\/2015\/17011"},{"key":"e_1_2_8_10_1","first-page":"27","article-title":"The Anticancer Profile of Benzimidazolium Salts and Their Metal Complexes","volume":"34","author":"Khan I. A.","year":"2022","journal-title":"Benzimidazole"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2010.01.067"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.3390\/metabo8020025"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.3389\/fmolb.2024.1338528"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202405876"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1080\/07391102.2023.2291163"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2016.1189422"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.4155\/fmc-2021-0222"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1042\/CS20210040"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201300228"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2013.03.077"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2019.03.010"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.4c05804"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202402893"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/fsn3.4531"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ica.2024.122190"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.poly.2024.117016"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1111\/cbdd.14482"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2023.106916"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2023.106513"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00044-023-03031-z"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.2174\/092986712801323225"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo991536"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.matlet.2025.139846"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2022.134320"},{"key":"e_1_2_8_35_1","volume-title":"CrysAlisPro Software System, Version 1.171.38.43","author":"Rigaku Corporation","year":"2015"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053273314026370"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889808042726"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053229614024218"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)95800-X"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1135914"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1094470"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2017.03.001"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2014.928704"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2012.670807"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(61)90145-9"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01318a036"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2022.133266"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2023.135640"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.23001"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2023.110094"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202200257"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10947-007-0108-7"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1080\/00958972.2018.1494269"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2017.11.079"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2018.05.077"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199515551"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1747-0285.2010.00965.x"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756360310001656736"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1080\/1475636040001704461"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.3906\/kim-1403-5"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcab.2019.101441"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2019.103096"},{"key":"e_1_2_8_63_1","doi-asserted-by":"publisher","DOI":"10.1006\/jmbi.1994.1655"},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0500908102"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0907444900010659"}],"container-title":["Journal of Biochemical and Molecular Toxicology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jbt.70893","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/jbt.70893","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jbt.70893","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T07:01:06Z","timestamp":1786950066000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/jbt.70893"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,25]]},"references-count":64,"journal-issue":{"issue":"8","published-print":{"date-parts":[[2026,8]]}},"alternative-id":["10.1002\/jbt.70893"],"URL":"https:\/\/doi.org\/10.1002\/jbt.70893","archive":["Portico"],"relation":{},"ISSN":["1095-6670","1099-0461"],"issn-type":[{"value":"1095-6670","type":"print"},{"value":"1099-0461","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,25]]},"assertion":[{"value":"2026-03-12","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-04-29","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-07-25","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e70893"}}