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In this study, a new series of 1,3,4\u2010oxadiazole derivatives was synthesized and evaluated for cytotoxic and multi\u2010target anticancer activities. Several compounds demonstrated potent antiproliferative effects against HepG2, MCF\u20107, and HCT\u2010116 cancer cell lines with reduced toxicity toward WI\u201038 normal fibroblasts. Among them, compounds\n                    <jats:bold>1<\/jats:bold>\n                    ,\n                    <jats:bold>9<\/jats:bold>\n                    ,\n                    <jats:bold>12<\/jats:bold>\n                    , and\n                    <jats:bold>13<\/jats:bold>\n                    emerged as the most promising candidates, showing strong cytotoxicity and favorable selectivity profiles. Enzyme inhibition assays confirmed their ability to target key oncogenic enzymes, including wild\u2010type and mutant (T790M) EGFR, telomerase, and thymidylate synthase. Mechanistic studies revealed that compound\n                    <jats:bold>12<\/jats:bold>\n                    induced G1 phase cell cycle arrest and promoted apoptosis in HepG2 cells with minimal necrosis. Molecular docking, molecular dynamics simulations, and MM\u2010GBSA analyses supported stable binding of the active compounds within the catalytic sites of the investigated enzymes. Overall, these findings identify compounds\n                    <jats:bold>1<\/jats:bold>\n                    ,\n                    <jats:bold>9<\/jats:bold>\n                    ,\n                    <jats:bold>12<\/jats:bold>\n                    , and\n                    <jats:bold>13<\/jats:bold>\n                    as promising multi\u2010target anticancer leads warranting further optimization and development.\n                  <\/jats:p>","DOI":"10.1002\/ddr.70268","type":"journal-article","created":{"date-parts":[[2026,3,29]],"date-time":"2026-03-29T16:34:11Z","timestamp":1774802051000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["PTC\u2010Assisted Chemoselective\n                    <i>S<\/i>\n                    \u2010Alkylation of 5\u2010Mercapto\u20101,3,4\u2010Oxadiazol Derivative: Multi\u2010Target Anticancer via EGFR, Telomerase, and Thymidylate Synthase Inhibition With Apoptosis Induction"],"prefix":"10.1002","volume":"87","author":[{"given":"Asmaa","family":"Zakaria","sequence":"first","affiliation":[{"name":"Chemistry Department, Faculty of Science Ain Shams University Cairo Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8173-6073","authenticated-orcid":false,"given":"Ahmed A.","family":"Al\u2010Karmalawy","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy The University of Mashreq Baghdad Iraq"},{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy Horus University\u2010Egypt New Damietta Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Samia S.","family":"Hawas","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy Horus University\u2010Egypt New Damietta Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ali Khalil","family":"Ali","sequence":"additional","affiliation":[{"name":"Chemistry Department, Faculty of Science Ain Shams University Cairo Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Galal A.","family":"Elsayed","sequence":"additional","affiliation":[{"name":"Chemistry Department, Faculty of Science Ain Shams University Cairo Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9445-3315","authenticated-orcid":false,"given":"Arwa Omar Al","family":"Khatib","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy Al\u2010Ahliyya Amman University Amman Jordan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3245-1653","authenticated-orcid":false,"given":"Eslam M.","family":"Abbass","sequence":"additional","affiliation":[{"name":"Chemistry Department, Faculty of Science Ain Shams University Cairo Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,3,29]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1080\/10406638.2023.2189736"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202301682"},{"key":"e_1_2_8_4_1","doi-asserted-by":"crossref","unstructured":"Ahmed M. 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