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All compounds were tested for their ability to inhibit the human carbonic anhydrase (<jats:italic>h<\/jats:italic>CA) isoforms I and II, and acetylcholinesterase (AChE). The halogen\u2010appended compounds, <jats:bold>7g<\/jats:bold>, <jats:bold>7o<\/jats:bold>, and <jats:bold>7i<\/jats:bold>, exhibited the highest <jats:italic>h<\/jats:italic>CA I\/II and AChE inhibition, with the <jats:italic>K<\/jats:italic><jats:sub>I<\/jats:sub> values in the low nanomolar range (<jats:italic>K<\/jats:italic><jats:sub>I<\/jats:sub>\u2009=\u20099.01\u2009\u00b1\u20090.08, 7.41\u2009\u00b1\u20090.03, and 7.37\u2009\u00b1\u20090.31\u2009nM, respectively), as compared with their corresponding parent 2\u2010[2,2\u2010dicyano\u20101\u2010(phenylamino)vinylthio]\u2010<jats:italic>N<\/jats:italic>\u2010(4\u2010sulfamoylphenyl)acetamide analogs <jats:bold>7a<\/jats:bold>\u2013<jats:bold>o<\/jats:bold>. Besides, derivatives <jats:bold>7c<\/jats:bold> and <jats:bold>7e<\/jats:bold> selectively inhibited the isoform <jats:italic>h<\/jats:italic>CA I, whereas compounds <jats:bold>7m<\/jats:bold> and <jats:bold>7n<\/jats:bold> selectively inhibited isoform <jats:italic>h<\/jats:italic>CA II. These findings indicated that all compounds can inhibit metabolic dysfunctions, such as edema, epilepsy, glaucoma, and Alzheimer's disease, by specifically targeting both the <jats:italic>h<\/jats:italic>CA isoforms and AChE expression. Herein, also the interactions between ligands and receptors were highlighted through in silico molecular docking studies. The molecular mechanics\u2013generalized Born surface area method was utilized to compute the binding free energy and the energy contribution of the critical residues in the active site was estimated. All these results would help us to perfectly understand the relationship between activity and structural characteristics of derivatives and to further improve newly and highly effective analogs targeting <jats:italic>h<\/jats:italic>CA and AChE.<\/jats:p>","DOI":"10.1002\/ardp.201900383","type":"journal-article","created":{"date-parts":[[2020,4,14]],"date-time":"2020-04-14T05:47:58Z","timestamp":1586843278000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":76,"title":["Sulfonamides incorporating ketene <i>N,S<\/i>\u2010acetal bioisosteres as potent carbonic anhydrase and acetylcholinesterase inhibitors"],"prefix":"10.1002","volume":"353","author":[{"given":"Q\u00ebndresa","family":"Istrefi","sequence":"first","affiliation":[{"name":"Department of Chemistry, Faculty of Mathematical and Natural Sciences University of Prishtina  Prishtina, Republic of Kosovo"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2932-2789","authenticated-orcid":false,"given":"C\u00fcneyt","family":"T\u00fcrke\u015f","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Faculty of Pharmacy Erzincan Binali Y\u0131ld\u0131r\u0131m University  Erzincan Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mustafa","family":"Arslan","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Arts and Sciences Sakarya University  Sakarya Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yeliz","family":"Demir","sequence":"additional","affiliation":[{"name":"Department of Pharmacy Services, Nihat Delibalta G\u00f6le Vocational High School Ardahan University  Ardahan Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arleta R.","family":"Nixha","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Mathematical and Natural Sciences University of Prishtina  Prishtina, Republic of Kosovo"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"\u015e\u00fckr\u00fc","family":"Beydemir","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Faculty of Pharmacy Anadolu University  Eski\u015fehir Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"\u00d6mer \u0130.","family":"K\u00fcfrevio\u011flu","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Sciences Atat\u00fcrk University  Erzurum Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,4,13]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00360"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1080\/01961779008048749"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1081\/SCC-100106218"},{"key":"e_1_2_8_5_1","doi-asserted-by":"crossref","first-page":"554","DOI":"10.16984\/saufenbilder.414310","volume":"23","author":"Berber N.","year":"2019","journal-title":"Sakarya University J. 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