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Compounds <jats:bold>ABQ3<\/jats:bold>, <jats:bold>ABQ11<\/jats:bold>, and <jats:bold>ABQ12<\/jats:bold> demonstrated a pronounced antiproliferative effect against chronic myelogenous leukemia (CML) K562 cell line with IC<jats:sub>50<\/jats:sub> values of 0.82\u00a0\u00b1\u00a00.07, 0.28\u00a0\u00b1\u00a00.03, and 0.98\u00a0\u00b1\u00a00.22\u00a0\u03bcM, respectively. Among them, <jats:bold>ABQ11<\/jats:bold> showed approximately three times higher selectivity than imatinib on CML. <jats:bold>ABQ11<\/jats:bold>\u2010treated CML cells induced significant apoptosis at low concentration. Inhibitory effect of <jats:bold>ABQ11<\/jats:bold> against eight different tyrosine kinases, including ABL1, was investigated. <jats:bold>ABQ11<\/jats:bold> inhibited ABL1 with IC<jats:sub>50<\/jats:sub> value of 13.12\u00a0\u00b1\u00a01.71\u00a0\u03bcM, indicating that the moderate inhibition of ABL1 kinase is just an in\u2010part mechanism of its outstanding cellular activity. Molecular docking of <jats:bold>ABQ11<\/jats:bold> into ABL1 kinase ATP\u2010binding pocket revealed the formation of some key interactions. Furthermore, DNA cleavage assay showed that <jats:bold>ABQ11<\/jats:bold> strongly disintegrated DNA at 1\u00a0\u03bcM concentration in the presence of iron (II) complex system, assuming that the major mechanism for the anticancer effects of <jats:bold>ABQ11<\/jats:bold> is DNA cleavage. In silico ADMET prediction revealed that <jats:bold>ABQ11<\/jats:bold> is a drug\u2010like small molecule with a favorable safety profile. Taken together, <jats:bold>ABQ11<\/jats:bold> is a potential antiproliferative hit compound that exhibits unique cytotoxic activity distinct from imatinib.<\/jats:p>","DOI":"10.1111\/cbdd.13651","type":"journal-article","created":{"date-parts":[[2019,12,2]],"date-time":"2019-12-02T10:08:43Z","timestamp":1575281323000},"page":"343-354","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":27,"title":["A novel series of chlorinated plastoquinone analogs: Design, synthesis, and evaluation of anticancer activity"],"prefix":"10.1111","volume":"95","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0777-4012","authenticated-orcid":false,"given":"Nil\u00fcfer","family":"Bayrak","sequence":"first","affiliation":[{"name":"Chemistry Department Engineering Faculty Istanbul University\u2010Cerrahpasa Istanbul Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3988-6120","authenticated-orcid":false,"given":"Hatice","family":"Y\u0131ld\u0131r\u0131m","sequence":"additional","affiliation":[{"name":"Chemistry Department Engineering Faculty Istanbul University\u2010Cerrahpasa Istanbul Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6317-5738","authenticated-orcid":false,"given":"Mahmut","family":"Y\u0131ld\u0131z","sequence":"additional","affiliation":[{"name":"Chemistry Department Gebze Technical University Kocaeli Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9220-2659","authenticated-orcid":false,"given":"Mohamed O.","family":"Radwan","sequence":"additional","affiliation":[{"name":"Department of Drug Discovery Science Farm Ltd. 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