{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,1]],"date-time":"2026-07-01T11:45:31Z","timestamp":1782906331793,"version":"3.54.5"},"reference-count":109,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2017,12,28]],"date-time":"2017-12-28T00:00:00Z","timestamp":1514419200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J Biochem &amp; Molecular Tox"],"published-print":{"date-parts":[[2018,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The conversion reactions of pyrimidine\u2010thiones with nucleophilic reagent were studied during this scientific research. For this purpose, new compounds were synthesized by the interaction between 1,2\u2010epoxy propane, 1,2\u2010epoxy butane, and 4\u2010chlor\u20101\u2010butanol and pyrimidine\u2010thiones. These pyrimidine\u2010thiones derivatives (<jats:bold>A\u2013K<\/jats:bold>) showed good inhibitory action against acetylcholinesterase (AChE), and human carbonic anhydrase (hCA) isoforms I and II. AChE inhibition was in the range of 93.1 \u00b1 33.7\u2013467.5 \u00b1 126.9\u00a0nM. The hCA I and II were effectively inhibited by these compounds, with<jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub>values in the range of 4.3 \u00b1 1.1\u20139.1 \u00b1 2.7\u00a0nM for hCA I and 4.2 \u00b1 1.1\u201314.1 \u00b1 4.4\u00a0nM for hCA II. On the other hand, acetazolamide clinically used as CA inhibitor showed<jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub>value of 13.9 \u00b1 5.1\u00a0nM against hCA I and 18.1 \u00b1 8.5\u00a0nM against hCA II. The antioxidant activity of the pyrimidine\u2010thiones derivatives (<jats:bold>A\u2013K<\/jats:bold>) was investigated by using different<jats:italic>in vitro<\/jats:italic>antioxidant assays, including Cu<jats:sup>2+<\/jats:sup>\u2009and Fe<jats:sup>3+<\/jats:sup>\u2009reducing, 1,1\u2010diphenyl\u20102\u2010picrylhydrazyl (DPPH<jats:sup>\u2022<\/jats:sup>) radical scavenging, and Fe<jats:sup>2+<\/jats:sup>\u2009chelating activities.<\/jats:p>","DOI":"10.1002\/jbt.22019","type":"journal-article","created":{"date-parts":[[2017,12,28]],"date-time":"2017-12-28T13:45:49Z","timestamp":1514468749000},"source":"Crossref","is-referenced-by-count":60,"title":["Synthesis and investigation of the conversion reactions of pyrimidine\u2010thiones with nucleophilic reagent and evaluation of their acetylcholinesterase, carbonic anhydrase inhibition, and antioxidant activities"],"prefix":"10.1002","volume":"32","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3171-0633","authenticated-orcid":false,"given":"Parham","family":"Taslimi","sequence":"first","affiliation":[{"name":"Department of Chemistry, Faculty of Sciences Ataturk University Erzurum 25240 Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Afsun","family":"Sujayev","sequence":"additional","affiliation":[{"name":"Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives Azerbaijan National Academy of Sciences Baku 1029 Azerbaijan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0538-3157","authenticated-orcid":false,"given":"Fikret","family":"Turkan","sequence":"additional","affiliation":[{"name":"Health Services Vocational School Igd\u0131r University Igd\u0131r 76000 Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emin","family":"Garibov","sequence":"additional","affiliation":[{"name":"Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives Azerbaijan National Academy of Sciences Baku 1029 Azerbaijan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7623-1492","authenticated-orcid":false,"given":"Z\u00fcbeyir","family":"Huyut","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Faculty of Medical Van Yuzuncu Yil University Van 65090 Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vagif","family":"Farzaliyev","sequence":"additional","affiliation":[{"name":"Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives Azerbaijan National Academy of Sciences Baku 1029 Azerbaijan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sevgi","family":"Mamedova","sequence":"additional","affiliation":[{"name":"Laboratory of Theoretical Bases of Synthesis and Action Mechanism of Additives, Institute of Chemistry of Additives Azerbaijan National Academy of Sciences Baku 1029 Azerbaijan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5993-1668","authenticated-orcid":false,"given":"\u0130lhami","family":"Gul\u00e7in","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Sciences Ataturk University Erzurum 25240 Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2017,12,28]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules17089868"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/cc0601377"},{"key":"e_1_2_7_4_1","doi-asserted-by":"crossref","first-page":"1957","DOI":"10.1021\/jo040281j","volume":"70","author":"Fu\u2010An K.","year":"2005","journal-title":"J. Org. Chem."},{"key":"e_1_2_7_5_1","doi-asserted-by":"crossref","first-page":"3797","DOI":"10.1021\/ol051458e","volume":"7","author":"Shenlin H.","year":"2005","journal-title":"Org. Lett."},{"issue":"2","key":"e_1_2_7_6_1","doi-asserted-by":"crossref","first-page":"130","DOI":"10.1002\/ptr.1821","volume":"20","author":"G\u00fcl\u00e7in \u0130.","year":"2006","journal-title":"Phytother. Res."},{"issue":"2","key":"e_1_2_7_7_1","first-page":"217","volume":"5","author":"K\u00f6ksal E.","year":"2011","journal-title":"J. Med. Plants Res."},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbi.2008.05.003"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2011.03.031"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2010.11.001"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2012.11.022"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201100272"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756360903514164"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201400257"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2015.04.019"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules190710103"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1556\/AVet.52.2004.4.4"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2012.10.024"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756360310001656736"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1248\/bpb.30.2257"},{"key":"e_1_2_7_21_1","first-page":"441","volume":"31","author":"Gocer H.","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem"},{"key":"e_1_2_7_22_1","first-page":"408","volume":"13","author":"G\u00fcl\u00e7in \u0130.","year":"2013","journal-title":"Mini. Rev. Med. Chem."},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2017.03.001"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2017.1368019"},{"key":"e_1_2_7_25_1","author":"Kocyigit U.M.","year":"2017","journal-title":"Arch. Physiol. Biochem"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.21938"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.21972"},{"key":"e_1_2_7_28_1","author":"Ko\u00e7yi\u011fit U. M.","year":"2017","journal-title":"J. Biochem. Mol. Toxicol"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2012.670807"},{"key":"e_1_2_7_30_1","doi-asserted-by":"crossref","first-page":"773","DOI":"10.3109\/14756366.2015.1064406","volume":"31","author":"Polat Kase L.","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.21973"},{"key":"e_1_2_7_32_1","author":"Taslimi P.","year":"2017","journal-title":"J. Biochem. Mol. Toxicol"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.12.054"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.3906\/kim-1403-5"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)95800-X"},{"key":"e_1_2_7_36_1","doi-asserted-by":"crossref","first-page":"2313","DOI":"10.1080\/00397911.2017.1373406","author":"Budak Y.","year":"2017","journal-title":"Synth. Commun"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.21971"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01318a036"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/0003-2697(76)90527-3"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.21931"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501573b"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(61)90145-9"},{"key":"e_1_2_7_43_1","author":"Yamali C.","year":"2017","journal-title":"Chem. Biol. Drug Des."},{"key":"e_1_2_7_44_1","doi-asserted-by":"crossref","first-page":"817","DOI":"10.1016\/S0022-3565(25)12939-X","volume":"277","author":"McKinzie S.","year":"1996","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201700045"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2017.07.010"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201300273"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2015.04.019"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.2174\/138620706777698544"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf980496s"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201500035"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.3109\/09637486.2011.585963"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tox.2005.09.011"},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.1006\/abbi.1994.1485"},{"key":"e_1_2_7_55_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.lfs.2005.05.103"},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1038\/1811199a0"},{"key":"e_1_2_7_57_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00726-006-0379-x"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0891-5849(98)00315-3"},{"key":"e_1_2_7_59_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756360701626223"},{"key":"e_1_2_7_60_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbi.2008.09.023"},{"key":"e_1_2_7_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201700198"},{"key":"e_1_2_7_62_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.etap.2016.04.011"},{"key":"e_1_2_7_63_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2016.04.002"},{"key":"e_1_2_7_64_1","doi-asserted-by":"publisher","DOI":"10.1002\/med.10025"},{"key":"e_1_2_7_65_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature06636"},{"key":"e_1_2_7_66_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms17101736"},{"key":"e_1_2_7_67_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1094470"},{"key":"e_1_2_7_68_1","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.2558"},{"key":"e_1_2_7_69_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-0348-8446-4_9"},{"key":"e_1_2_7_70_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijbiomac.2016.10.096"},{"key":"e_1_2_7_71_1","doi-asserted-by":"publisher","DOI":"10.2174\/1389557043487402"},{"key":"e_1_2_7_72_1","doi-asserted-by":"publisher","DOI":"10.1517\/13543776.13.10.1545"},{"key":"e_1_2_7_73_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.arabjc.2014.08.005"},{"key":"e_1_2_7_74_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.indcrop.2015.05.034"},{"key":"e_1_2_7_75_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ifset.2009.07.002"},{"key":"e_1_2_7_76_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00204-011-0774-2"},{"key":"e_1_2_7_77_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fct.2010.05.053"},{"key":"e_1_2_7_78_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-8741(03)00036-9"},{"key":"e_1_2_7_79_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00217-006-0265-5"},{"key":"e_1_2_7_80_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00226-008-0234-1"},{"key":"e_1_2_7_81_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.arabjc.2010.09.016"},{"key":"e_1_2_7_82_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2011.604318"},{"key":"e_1_2_7_83_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.arabjc.2009.12.008"},{"key":"e_1_2_7_84_1","first-page":"175","volume":"34","author":"G\u00fcl\u00e7in \u0130.","year":"2010","journal-title":"Turk. J. Biol."},{"key":"e_1_2_7_85_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2003.09.028"},{"key":"e_1_2_7_86_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1054820"},{"key":"e_1_2_7_87_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1014476"},{"key":"e_1_2_7_88_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010119)40:2<389::AID-ANIE389>3.0.CO;2-#"},{"key":"e_1_2_7_89_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biopha.2017.01.003"},{"key":"e_1_2_7_90_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2015.04.006"},{"key":"e_1_2_7_91_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201600183"},{"key":"e_1_2_7_92_1","doi-asserted-by":"publisher","DOI":"10.1002\/jbt.21897"},{"key":"e_1_2_7_93_1","doi-asserted-by":"publisher","DOI":"10.2174\/1570180814666161128120612"},{"key":"e_1_2_7_94_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2016.1238367"},{"key":"e_1_2_7_95_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2016.1170014"},{"key":"e_1_2_7_96_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2016.1198901"},{"key":"e_1_2_7_97_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2016.1189422"},{"key":"e_1_2_7_98_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2016.1156104"},{"key":"e_1_2_7_99_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2016.1160077"},{"key":"e_1_2_7_100_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2010.01.076"},{"key":"e_1_2_7_101_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2014.07.009"},{"key":"e_1_2_7_102_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1135914"},{"key":"e_1_2_7_103_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.04.007"},{"key":"e_1_2_7_104_1","doi-asserted-by":"publisher","DOI":"10.1111\/cbdd.12695"},{"key":"e_1_2_7_105_1","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.201300228"},{"key":"e_1_2_7_106_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1132710"},{"key":"e_1_2_7_107_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2015.1014474"},{"key":"e_1_2_7_108_1","doi-asserted-by":"publisher","DOI":"10.1080\/14756366.2016.1244533"},{"key":"e_1_2_7_109_1","doi-asserted-by":"publisher","DOI":"10.1248\/bpb.27.613"},{"key":"e_1_2_7_110_1","doi-asserted-by":"publisher","DOI":"10.3109\/14756366.2014.999236"}],"container-title":["Journal of Biochemical and Molecular Toxicology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fjbt.22019","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jbt.22019","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,6,29]],"date-time":"2025-06-29T08:29:37Z","timestamp":1751185777000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/jbt.22019"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,12,28]]},"references-count":109,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2018,2]]}},"alternative-id":["10.1002\/jbt.22019"],"URL":"https:\/\/doi.org\/10.1002\/jbt.22019","archive":["Portico"],"relation":{},"ISSN":["1095-6670","1099-0461"],"issn-type":[{"value":"1095-6670","type":"print"},{"value":"1099-0461","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,12,28]]},"article-number":"e22019"}}