Identification of ortho-naphthoquinones as anti-AML agents by highly efficient oxidation of phenols

Emadi, 2014, The state of the union on treatment of acute myeloid leukemia, Leukemia Lymphoma, 55, 2423, 10.3109/10428194.2014.897705 Oran, 2012, Survival for older patients with acute myeloid leukemia: a population-based study, Haematologica, 97, 1916, 10.3324/haematol.2012.066100 Arber, 2016, The 2016 revision to the World Health Organization classification of myeloid neoplasms and acute leukemia, Blood, 127, 2391, 10.1182/blood-2016-03-643544 Dohner, 2010, Diagnosis and management of acute myeloid leukemia in adults: recommendations from an international expert panel, on behalf of the European LeukemiaNet, Blood, 115, 53, 10.1182/blood-2009-07-235358 Patel, 2012, Prognostic relevance of integrated genetic profiling in acute myeloid leukemia, N. Engl. J. Med., 366, 1079, 10.1056/NEJMoa1112304 Papaemmanuil, 2016, Genomic classification and prognosis in acute myeloid leukemia, N. Engl. J. Med., 374, 2209, 10.1056/NEJMoa1516192 Hole, 2011, Do reactive oxygen species play a role in myeloid leukemias?, Blood, 117, 5816, 10.1182/blood-2011-01-326025 Carter-Cooper, 2017, Synthesis, characterization and antineoplastic activity of bis-aziridinyl dimeric naphthoquinone – a novel class of compounds with potent activity against acute myeloid leukemia cells, Bioorg. Med. Chem. Lett., 27, 6, 10.1016/j.bmcl.2016.11.045 Gorrini, 2013, Modulation of oxidative stress as an anticancer strategy, Nat. Rev. Drug Discov., 12, 931, 10.1038/nrd4002 Solivio, 2012, Biologically relevant oxidants cause bound proteins to readily oxidatively cross-link at Guanine, Chem. Res. Toxicol., 25, 326, 10.1021/tx200376e Ohayon, 2015, Harnessing the oxidation susceptibility of deubiquitinases for inhibition with small molecules, Angew. Chem. Int. Ed., 54, 599 Zhang, 2017, 2-Substituted 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-diones as specific L-shaped NQO1-mediated redox modulators for the treatment of non-small cell lung cancer, Eur. J. Med. Chem., 138, 616, 10.1016/j.ejmech.2017.06.028 Bian, 2014, 2-Substituted 3-methylnaphtho[1,2-b]furan-4,5-diones as novel L-shaped ortho-quinone substrates for NAD(P)H:quinone oxidoreductase (NQO1), Eur. J. Med. Chem., 82, 56, 10.1016/j.ejmech.2014.05.041 Bian, 2015, Synthesis and evaluation of (±)-dunnione and its orthoquinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1), Bioorg. Med. Chem. Lett., 25, 1244, 10.1016/j.bmcl.2015.01.057 Bian, 2017, Discovery of quinonedirected antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile, Eur. J. Med. Chem., 129, 27, 10.1016/j.ejmech.2017.02.004 Manickam, 2018, Investigation of chemical reactivity of 2-alkoxy-1,4-naphthoquinones and their anticancer activity, Bioorg. Med. Chem. Lett., 28, 2023, 10.1016/j.bmcl.2018.04.060 Cardoso, 2014, Synthesis and evaluation of the cytotoxic activity of 1,2-furanonaphthoquinones tethered to 1,2,3–1H-triazoles in myeloid and lymphoid leukemia cell lines, Eur. J. Med. Chem., 84, 708, 10.1016/j.ejmech.2014.07.079 Liu, 2012, Antiandrogenic, maspin induction, and antiprostate cancer activities of tanshinone IIA and its novel derivatives with modification in ring A, J. Med. Chem., 55, 971, 10.1021/jm2015292 Shen, 2009, Natural tanshinone-like heterocyclic-fused ortho-quinones from regioselective Diels-Alder reaction: synthesis and cytotoxicity evaluation, Eur. J. Med. Chem., 44, 3915, 10.1016/j.ejmech.2009.04.016 Antczak, 2011, Identification of benzofuran-4,5-diones as novel and selective non-hydroxamic acid, non-peptidomimetic based inhibitors of human peptide deformylase, Bioorg. Med. Chem. Lett., 21, 4528, 10.1016/j.bmcl.2011.05.129 Cedeno, 2012, Catalytic oxidation of para-substituted phenols with cobalt–Schiff base complexes/O2—selective conversion of syringyl and guaiacyl lignin models to benzoquinones, Trtrahedron Lett., 53, 2380, 10.1016/j.tetlet.2012.02.093 Morin, 2008, The aza-analogues of 1,4-naphthoquinones are potent substrates and inhibitors of plasmodial thioredoxin and glutathione reductases and of human erythrocyte glutathione reductase, Org. Biomol. Chem., 6, 2731, 10.1039/b802649c Biannic, 2013, Efficient cobalt-catalyzed oxidative conversion of lignin models to benzoquinones, Org. Lett., 15, 2730, 10.1021/ol401065r Cozzi, 2004, Metal-Salen Schiff base complexes in catalysis: practical aspects, Chem. Soc. Rev., 33, 410, 10.1039/B307853C