{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T14:07:28Z","timestamp":1790690848730,"version":"4.1.0"},"reference-count":50,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T00:00:00Z","timestamp":1790553600000},"content-version":"vor","delay-in-days":27,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2026,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Antioxidants neutralize free radicals to reduce oxidative stress and cellular damage, preventing various chronic diseases. In this study, the antioxidant activities of novel 5\u2010(trifluoromethyl)\u20103\n                    <jats:italic>H<\/jats:italic>\n                    \u2010spiro[1,3\u2010benzothiazole\u20102,3\u2032\u2010indol]\u20102\u2032(1\u2032\n                    <jats:italic>H<\/jats:italic>\n                    )\u2010ones (\n                    <jats:bold>4a\u2013h<\/jats:bold>\n                    ), along with the spirocyclic 2\u2010indolinones (\n                    <jats:bold>4i\u2013m<\/jats:bold>\n                    and\n                    <jats:bold>5a\u2013n<\/jats:bold>\n                    ) previously synthesized by our group, were investigated for the first time, to find a multi\u2010modal antioxidant and to understand the impact of the trifluoromethyl group located at the 5\u2010position of the benzothiazole on antioxidant activity. For this purpose, the 2,2\u2010diphenyl\u20101\u2010picrylhydrazyl (DPPH\u2022) free radical scavenging, superoxide anion scavenging, ABTS\n                    <jats:sup>\u2022+<\/jats:sup>\n                    radical cation scavenging, trolox equivalent antioxidant capacity, ferric ion reduction antioxidant potential (FRAP), and lipid peroxidation (TBARs) assays were carried out. The cytotoxic effects of compounds (\n                    <jats:bold>4g<\/jats:bold>\n                    ,\n                    <jats:bold>4h<\/jats:bold>\n                    ,\n                    <jats:bold>4i<\/jats:bold>\n                    ,\n                    <jats:bold>4j<\/jats:bold>\n                    ,\n                    <jats:bold>4l<\/jats:bold>\n                    ,\n                    <jats:bold>5a<\/jats:bold>\n                    ,\n                    <jats:bold>5b<\/jats:bold>\n                    , and\n                    <jats:bold>5h)<\/jats:bold>\n                    , which showed promising in vitro antioxidant activity in at least two in vitro tests, were investigated in healthy human fibroblast (HFF\u20101) cells. The effects of non\u2010toxic doses of these compounds on intracellular reactive oxygen species were also evaluated. As a result, it was determined that compound\n                    <jats:bold>4l<\/jats:bold>\n                    (R\n                    <jats:sub>1<\/jats:sub>\n                    \u2009=\u20095\u2010F and R\n                    <jats:sub>2<\/jats:sub>\n                    \u2009=\u2009H) exhibited greater radical scavenging activity than the other compounds tested. The IC\n                    <jats:sub>50<\/jats:sub>\n                    of compound\n                    <jats:bold>4l<\/jats:bold>\n                    was 74.13\u2009\u00b5M while compound\n                    <jats:bold>4g<\/jats:bold>\n                    (R\n                    <jats:sub>1<\/jats:sub>\n                    \u2009=\u20095\u2010Cl\u20107\u2010CH\n                    <jats:sub>3<\/jats:sub>\n                    and R\n                    <jats:sub>2<\/jats:sub>\n                    \u2009=\u2009H) was non\u2010toxic (IC\n                    <jats:sub>50<\/jats:sub>\n                    \u2009&gt;\u2009200 \u03bcM). Compounds\n                    <jats:bold>4e<\/jats:bold>\n                    (R\n                    <jats:sub>1<\/jats:sub>\n                    \u2009=\u20095\u2010Cl and R\n                    <jats:sub>2<\/jats:sub>\n                    \u2009=\u2009H) and\n                    <jats:bold>4f<\/jats:bold>\n                    (R\n                    <jats:sub>1<\/jats:sub>\n                    \u2009=\u20097\u2010Br and R\n                    <jats:sub>2<\/jats:sub>\n                    \u2009=\u2009H), exhibited higher lipid peroxidation inhibitory activity than \u03b1\u2010tocopherol in vitro; however, the difference was not statistically significant.\n                  <\/jats:p>","DOI":"10.1002\/ardp.70343","type":"journal-article","created":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T10:08:35Z","timestamp":1790590115000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Spirooxindole 5\u2010(Trifluoromethyl)benzothiazole Hybrids: Synthesis, Crystal Structure, and Antioxidant Activity"],"prefix":"10.1002","volume":"359","author":[{"given":"Nida","family":"Karabag","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy Istanbul University Istanbul Turkey"},{"name":"Department of Pharmaceutical Chemistry Institute of Health Sciences, Istanbul University Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1811-093X","authenticated-orcid":false,"given":"Asu Busra","family":"Temizer\u2010Keser","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry Institute of Health Sciences, Istanbul University Istanbul Turkey"},{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy Istanbul University\u2010Cerrahpa\u015fa Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6150-8372","authenticated-orcid":false,"given":"Murat","family":"Pekmez","sequence":"additional","affiliation":[{"name":"Department of Molecular Biology and Genetics, Faculty of Science Istanbul University Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3606-4722","authenticated-orcid":false,"given":"Elif","family":"Merto\u011flu\u2010Kamal\u0131","sequence":"additional","affiliation":[{"name":"Department of Molecular Biology and Genetics, Faculty of Science Istanbul University Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Filiz Bet\u00fcl","family":"Kaynak","sequence":"additional","affiliation":[{"name":"Department of Physical Engineering, Faculty of Engineering Hacettepe University Ankara Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nurten","family":"\u00d6zsoy","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Faculty of Pharmacy Istanbul University Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1043-5652","authenticated-orcid":false,"given":"Nazl\u0131","family":"Arda","sequence":"additional","affiliation":[{"name":"Department of Molecular Biology and Genetics, Faculty of Science Istanbul University Istanbul Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6916-122X","authenticated-orcid":false,"given":"Nilg\u00fcn","family":"Karal\u0131","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy Istanbul University Istanbul 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