Synthesis,Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone |
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| Authors: | Ryuta Inagaki Masayuki Ninomiya Prof. Kaori Tanaka Prof. Mamoru Koketsu |
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| Affiliation: | 1. Department of Materials Science and Technology, Faculty of Engineering, Gifu University, 1‐1 Yanagido, Gifu 501‐1193 (Japan);2. Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1‐1 Yanagido, Gifu 501‐1193 (Japan);3. Division of Anaerobe Research, Life Science Research Center, Gifu University, 1‐1 Yanagido, Gifu 501‐1194 (Japan);4. United Graduate School of Drug Discovery and Medicinal Information Sciences, Gifu University, 1‐1 Yanagido, Gifu 501‐1194 (Japan) |
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| Abstract: | Naphthoquinones are considered privileged structures for anticancer drug molecules. The Heck reaction of 2‐hydroxy‐1,4‐naphthoquinone (lawsone) with 1‐bromo‐3‐methyl‐2‐butene offered easy access to lapachol. Several naturally occurring linear and angular heterocyclic quinoids (α‐lapachone, β‐lapachone, dunnione, and related analogues) were prepared from lapachol. Furthermore, we demonstrated that the synthetic naphthoquinones inhibit cell proliferation in human leukemia HL‐60 cells. In particular, angular‐type derivatives were found to possess moderate cytotoxicity and to elevate the levels of intracellular glutathione disulfide (GSSG). Our work highlights the significant potential of naturally occurring angular‐series naphthoquinones as antileukemic agents. |
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| Keywords: | antileukemic activity glutathione lapachol natural products quinones |
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