64469-16-5Relevant academic research and scientific papers
Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone
Inagaki, Ryuta,Ninomiya, Masayuki,Tanaka, Kaori,Koketsu, Mamoru
, p. 1413 - 1423 (2015/08/03)
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.
Palladium-catalyzed allylation of 2-hydroxy-1,4-naphthoquinone: Application to the preparation of lapachol
Kazantzi, Georgia,Malamidou-Xenikaki, Elizabeth,Spyroudis, Spyros
, p. 427 - 430 (2008/01/03)
The Pd(PPh3)4-catalyzed reaction of 2-hydroxy-1,4-naphthoquinone (lawsone) with allyl alcohols and allyl esters offers an easy access to 3-allyl-2-hydroxy-1,4-naphthoquinones, compounds with interesting biological activity. The reaction finds application in the preparation of lapachol. Other 2-hydroxy-1,4-benzoquinones give allylation products in low yields. Georg Thieme Verlag Stuttgart.
