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In this study, a novel series of benzimidazolone\u2010based hybrids incorporating piperazine, coumarin, and triazole moieties was designed, synthesized, and evaluated for inhibitory activity against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and monoamine oxidase\u2010B (MAO\u2010B), as well as antioxidant potential via on\u2010line HPLC\u2010based assays. Structures were confirmed by\n                    <jats:sup>1<\/jats:sup>\n                    H\u2010NMR,\n                    <jats:sup>13<\/jats:sup>\n                    C\u2010NMR (APT), and elemental analysis. Several compounds showed notable, micromolar\u2010range inhibitory activity, though less potent than the reference drugs. Kinetic analysis showed that the leading compounds inhibited their respective enzymes via a mixed\u2010type mechanism. Compound\n                    <jats:bold>1<\/jats:bold>\n                    showed the strongest AChE inhibition (IC\n                    <jats:sub>50<\/jats:sub>\n                    \u2009=\u20090.777\u2009\u00b1\u20090.014\u2009\u00b5M), compound\n                    <jats:bold>9b<\/jats:bold>\n                    the highest BChE inhibition (IC\n                    <jats:sub>50<\/jats:sub>\n                    \u2009=\u20090.659\u2009\u00b1\u20090.005\u2009\u00b5M), and compound\n                    <jats:bold>9c<\/jats:bold>\n                    the most potent MAO\u2010B inhibition (IC\n                    <jats:sub>50<\/jats:sub>\n                    \u2009=\u20092.431\u2009\u00b1\u20090.003\u2009\u00b5M). Compound\n                    <jats:bold>8a<\/jats:bold>\n                    showed the highest CUPRAC copper\u2010reducing capacity, while\n                    <jats:bold>7c<\/jats:bold>\n                    displayed the strongest DPPH radical\u2010scavenging activity. Liposomal formulations of\n                    <jats:bold>4c<\/jats:bold>\n                    ,\n                    <jats:bold>7c<\/jats:bold>\n                    , and\n                    <jats:bold>8a<\/jats:bold>\n                    exhibited enhanced antioxidant responses relative to their free forms. In silico ADME predictions (SwissADME) indicated favorable drug\u2010likeness and blood\u2013brain barrier permeation for the compact scaffold (compound\n                    <jats:bold>1<\/jats:bold>\n                    ) and the piperazine\u2010based hybrids, whereas the larger bis\u2010conjugated derivatives were limited by high polarity and molecular weight. Overall, these benzimidazolone\u2010based hybrids represent promising multi\u2010target candidates for AD drug development.\n                  <\/jats:p>","DOI":"10.1002\/ddr.70369","type":"journal-article","created":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T15:08:09Z","timestamp":1787238489000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Design, Synthesis, and Biological Evaluation of Benzimidazol\u20102\u2010One Hybrids as Potential Anti\u2010Alzheimer's Disease Agents"],"prefix":"10.1002","volume":"87","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6666-3566","authenticated-orcid":false,"given":"Fatih","family":"Y\u0131lmaz","sequence":"first","affiliation":[{"name":"Department of Chemistry and Chemical Process Technology, Vocational School of Technical Sciences Recep Tayyip Erdogan University Rize Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3408-8202","authenticated-orcid":false,"given":"Emre","family":"Mente\u015fe","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Art and Sciences Recep Tayyip Erdogan University Rize Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4449-0537","authenticated-orcid":false,"given":"Ozan Emre","family":"Ey\u00fcpo\u011flu","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, School of Pharmacy Istanbul Medipol University Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bahittin","family":"Kahveci","sequence":"additional","affiliation":[{"name":"Department of Nutrition and Dietetics, Faculty of Health Sciences Karadeniz Technical University Trabzon Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9489-9093","authenticated-orcid":false,"given":"Mustafa","family":"Emirik","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Art and Sciences Recep Tayyip Erdogan University Rize Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,8,20]]},"reference":[{"key":"e_1_2_11_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc500509a"},{"key":"e_1_2_11_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.heliyon.2019.e01552"},{"key":"e_1_2_11_4_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules29030674"},{"key":"e_1_2_11_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf048741x"},{"issue":"1","key":"e_1_2_11_6_1","first-page":"S49","article-title":"Limit of Blank, Limit of Detection and Limit of Quantitation","volume":"29","author":"Armbruster D. 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