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Cytotoxic activities and carbonic anhydrase (CA) inhibitory effects of the compounds were studied to identify new possible drug candidate molecules. Cytotoxicity results pointed out that compound <jats:bold>2m<\/jats:bold>, 6\u2010[3\u2010(3\u2010bromophenyl)\u20102\u2010propenoyl]\u20102(3<jats:italic>H<\/jats:italic>)\u2010benzoxazolone, had the highest cytotoxicity (CC<jats:sub>50<\/jats:sub>) and potency selectivity expression (PSE) values. Thus, compound <jats:bold>2m<\/jats:bold> can be considered as a lead compound of the series in terms of cytotoxicity. When the CA inhibition results of the compounds were evaluated, it was found that the <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values of the compounds ranged from 30.5\u2009\u00b1\u200911.3 to 65.5\u2009\u00b1\u200925.6\u2009\u00b5M toward hCA I, and they ranged from 7.3\u2009\u00b1\u20091.8 to 58.8\u2009\u00b1\u200912.3\u2009\u00b5M toward hCA II. However, the <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values of the reference drug, acetazolamide (AZA), were 30.2\u2009\u00b1\u20097.8 and 4.4\u2009\u00b1\u20090.6\u2009\u03bcM toward hCA I and hCA II, respectively. According to the results obtained, compounds <jats:bold>2a<\/jats:bold>\u2013<jats:bold>n<\/jats:bold> had lower <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values than AZA, whereas compounds <jats:bold>2a<\/jats:bold>, <jats:bold>2b<\/jats:bold>, <jats:bold>2e<\/jats:bold>\u2013<jats:bold>g<\/jats:bold>, <jats:bold>2l<\/jats:bold>, and <jats:bold>2n<\/jats:bold> had similar <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values, compared with AZA. So, the compounds <jats:bold>2a<\/jats:bold>, <jats:bold>2b<\/jats:bold>, <jats:bold>2e<\/jats:bold>\u2013<jats:bold>g<\/jats:bold>, <jats:bold>2l<\/jats:bold>, and <jats:bold>2n<\/jats:bold> can be considered as lead molecules of this series for further considerations.<\/jats:p>","DOI":"10.1002\/ardp.201900384","type":"journal-article","created":{"date-parts":[[2020,4,14]],"date-time":"2020-04-14T07:44:03Z","timestamp":1586850243000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["New halogenated chalcones with cytotoxic and carbonic anhydrase inhibitory properties: 6\u2010(3\u2010Halogenated phenyl\u20102\u2010propen\u20101\u2010oyl)\u20102(3<i>H<\/i>)\u2010benzoxazolones"],"prefix":"10.1002","volume":"353","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5676-2045","authenticated-orcid":false,"given":"Sinan","family":"Bilginer","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy Ataturk University  Erzurum Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Halise I.","family":"Gul","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy Ataturk University  Erzurum Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Feyza S.","family":"Erdal","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy Ataturk University  Erzurum Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroshi","family":"Sakagami","sequence":"additional","affiliation":[{"name":"Meikai University School of Dentistry Meikai University Research Institute of Odontology (M\u2010RIO)  Sakado Saitama Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ilhami","family":"Gulcin","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science Ataturk University  Erzurum Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,4,14]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/ijc.31937"},{"key":"e_1_2_7_3_1","volume-title":"Anticancer Drugs, Pharmaceutical Chemistry","author":"Palaska E.","year":"2004"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2019.1670657"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2007.04.020"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2019.1626376"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1042\/BCJ20160115"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.2174\/138161208783877910"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1042\/BJ20051102"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2004.07.086"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.2174\/138161208783877884"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr200176r"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2018.02.015"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1517\/13543776.2013.790957"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1080\/17460441.2017.1253677"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2018.1428572"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756360802399126"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/jps.2600830420"},{"key":"e_1_2_7_19_1","first-page":"182","volume":"52","author":"Dimmock J.","year":"1997","journal-title":"Pharmazie"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.2174\/092986709788682218"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/0304-419X(85)90009-5"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.124.3235.1292-a"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/0223-5234(88)90182-1"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/0223-5234(93)90148-8"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.200900308"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2014.08.033"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0024-3205(99)00120-4"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11164-017-2977-5"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2016.1221825"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2006.09.019"},{"key":"e_1_2_7_31_1","first-page":"481","volume":"10","author":"De R. 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