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The synthetic route involved the formation of intermediate hydrazides, their condensation with carbon disulfide, and intramolecular cyclization to corresponding 5\u2010[(1\n                    <jats:italic>H<\/jats:italic>\n                    \u2010indol\u20103\u2010yl)methyl]\u20101,3,4\u2010oxadiazole\u20102(3\n                    <jats:italic>H<\/jats:italic>\n                    )\u2010thiones. The latter were then S\u2010alkylated, and in case of ester derivatives, they were further hydrolyzed into corresponding carboxylic acids. All 5\u2010[(1\n                    <jats:italic>H<\/jats:italic>\n                    \u2010indol\u20103\u2010yl)methyl]\u20101,3,4\u2010oxadiazole\u20102(3\n                    <jats:italic>H<\/jats:italic>\n                    )\u2010thiones and their S\u2010alkylated derivatives were then screened for their protective effects in vitro and in vivo. Methyl substitution on the indole ring and propyl, butyl, or benzyl substitution on sulfhydryl group\u2010possessing compounds were revealed to protect Friedreich's ataxia fibroblasts against the effects of glutathione depletion induced by the \u03b3\u2010glutamylcysteine synthetase inhibitor, buthionine sulfoximine. Two of the active compounds also reproducibly increased the survival of\n                    <jats:italic>Caenorhabditis elegans<\/jats:italic>\n                    exposed to juglone\u2010induced oxidative stress.\n                  <\/jats:p>","DOI":"10.1002\/ardp.202100001","type":"journal-article","created":{"date-parts":[[2021,3,18]],"date-time":"2021-03-18T03:22:37Z","timestamp":1616037757000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Synthesis of 5\u2010[(1\n                    <i>H<\/i>\n                    \u2010indol\u20103\u2010yl)methyl]\u20101,3,4\u2010oxadiazole\u20102(3\n                    <i>H<\/i>\n                    )\u2010thiones and their protective activity against oxidative stress"],"prefix":"10.1002","volume":"354","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7946-6780","authenticated-orcid":false,"given":"Monika","family":"I\u0161kauskien\u0117","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry Kaunas University of Technology  Kaunas Lithuania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2200-3977","authenticated-orcid":false,"given":"Alena","family":"Kadlecov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Experimental Biology, Faculty of Science Palack\u00fd University  Olomouc Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7378-8941","authenticated-orcid":false,"given":"Ji\u0159\u00ed","family":"Voller","sequence":"additional","affiliation":[{"name":"Department of Clinical and Molecular Pathology, Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry Palack\u00fd University  Olomouc Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6198-892X","authenticated-orcid":false,"given":"Lucie","family":"Janovsk\u00e1","sequence":"additional","affiliation":[{"name":"Department of Microbiology, Faculty of Medicine and Dentistry Palack\u00fd University  Olomouc Czech Republic"},{"name":"Laboratory of Growth Regulators, Institute of Experimental Botany of the Czech Academy of Sciences &amp; Faculty of Science Palack\u00fd University  Olomouc Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1342-9629","authenticated-orcid":false,"given":"Vida","family":"Malinauskien\u0117","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry Kaunas University of Technology  Kaunas Lithuania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6759-8789","authenticated-orcid":false,"given":"Asta","family":"\u017dukauskait\u0117","sequence":"additional","affiliation":[{"name":"Department of Chemical Biology, Faculty of Science Palack\u00fd University  Olomouc Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1514-4934","authenticated-orcid":false,"given":"Algirdas","family":"\u0160a\u010dkus","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry Kaunas University of Technology  Kaunas Lithuania"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,3,18]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm2013248"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.2174\/1389557518666181015152433"},{"key":"e_1_2_7_4_1","first-page":"435","volume":"29","author":"Pitasse\u2010Santos P.","year":"2018","journal-title":"J. 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