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The <jats:italic>O<\/jats:italic>\u2010substituted tetrafluoronaphthalene derivatives were designed and also synthesized via a one\u2010pot nucleophilic substitution reaction in excellent yields, whereas the tetrafluorotetrahydroepoxynaphthalene derivate was synthesized via a reduction reaction in excellent yield. The chemical structures of all the synthesized molecules were characterized by nuclear magnetic resonance, infrared spectroscopy, and high\u2010resolution mass spectrometry techniques. In this study, a series of novel tetrafluoronaphthalene derivatives (<jats:bold>2<\/jats:bold>, <jats:bold>2a<\/jats:bold>, <jats:bold>4<\/jats:bold>\u2013<jats:bold>6<\/jats:bold>) was tested toward\u00a0several enzymes including \u03b1\u2010glucosidase, acetylcholinesterase (AChE), and human carbonic anhydrase I and II (hCA I\/II). The tetrafluoronaphthalene derivatives <jats:bold>2<\/jats:bold>, <jats:bold>2a<\/jats:bold>, and <jats:bold>4<\/jats:bold>\u2013<jats:bold>6<\/jats:bold> showed IC<jats:sub>50<\/jats:sub> and <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values in the range of 0.83\u20131.27 and 0.71\u20131.09\u2009nM against hCA I, 1.26\u20131.85 and 1.45\u20135.31\u2009nM against hCA II, 39.02\u201356.01 and 20.53\u201356.76\u2009nM against\u00a0AChE, and 15.27\u201334.12 and 22.58\u201330.45\u2009nM against \u03b1\u2010glucosidase, respectively. Molecular docking calculations were made to determine the biological activity values of the tetrafluoronaphthalene derivatives against the enzymes. After the calculations, ADME\/T analysis was performed to examine the effects on human metabolism. Finally, these compounds had antidiabetic and anticholinesterase potentials.<\/jats:p>","DOI":"10.1002\/ardp.202000409","type":"journal-article","created":{"date-parts":[[2021,3,5]],"date-time":"2021-03-05T10:50:30Z","timestamp":1614941430000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Synthesis and docking calculations of tetrafluoronaphthalene derivatives and their inhibition profiles against some metabolic enzymes"],"prefix":"10.1002","volume":"354","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6097-2862","authenticated-orcid":false,"given":"Musa","family":"Erdo\u011fan","sequence":"first","affiliation":[{"name":"Department of Food Engineering, Faculty of Engineering and Architecture Kafkas University  Kars Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3171-0633","authenticated-orcid":false,"given":"Parham","family":"Taslimi","sequence":"additional","affiliation":[{"name":"Department of Biotechnology, Faculty of Science Bartin University  Bartin Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0420-2043","authenticated-orcid":false,"given":"Burak","family":"Tuzun","sequence":"additional","affiliation":[{"name":"Chemistry Department, Science Faculty Sivas Cumhuriyet University  Sivas Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,3,5]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200301023"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.5b00258"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1131943"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2020.109718"},{"key":"e_1_2_8_6_1","first-page":"1980","volume-title":"J. 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