137493-02-8Relevant articles and documents
Conversion of lapachol to lomatiol: Synthesis of novel naphthoquinone derivatives
Eyong, Kenneth O.,Chinthapally, Kiran,Senthilkumar, Soundararasu,Lamsh?ft, Marc,Folefoc, Gabriel N.,Baskaran, Sundarababu
, p. 9611 - 9616 (2015)
Lapachol (1), a naphthoquinone isolated mostly from the plants of the bignoniaceae family has a broad spectrum of biological activities and as a consequence it has been the object of different chemical transformations. Lomatiol (3), another naturally occurring naphthoquinone having structural similarities to lapachol, has been obtained from chemical and microbial transformations of lapachol in very low yields. In the present study, an easy approach for the synthesis of lomatiol (3) from lapachol (1) has been developed using SeO2 oxidation in 90% yield. Lomatiol, under epoxidation conditions afforded novel furano- and pyrano-naphthoquinone derivatives, which are analogues of anticancer agents, 2-acetylfuronaphthoquinone and β-lapachone. Most of the structures were unambiguously confirmed by single crystal X-ray analysis.
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.
Chemistry of lapachol - Syntheses of some new biogenetically related naphthoquinones, naphthoquinone dimers, naphthaquinoxaline and naphtha-azaquinoxaline derivatives from lapachol
Singh, Pahup,Krishna, Vivek,Khandelwal, Poonam,Sharma, Kuldeep K.,Sharma
experimental part, p. 85 - 95 (2011/07/30)
The present short review focus on chemical transformations of lapachol to a large number of biogenetically related lapachol conegeners, dimers and heterocyclic analogues that have been achieved in our laboratory during more than two decades. Conversion of lapachol to stenocarpoquinone-B, rhinacanthin-A, β-(l-hydroxyisopropanyl)-dihydrofurano-1,2-naphthoquinone, stenocarpoquinone-A, dehydro-α-lapachone and dehydro-β-lapachone by the reaction with m-chloroperbenzoic acid; dehydroiso-α-lapachone, dehydroiso-β-lapachone, dehydro-α-lapachone, α-lapachone and β-lapachone by the reaction with aqueous NaNO2 and glacial AcOH; adenophyllone, quadrllone and dehydro-α-lapachone by the reaction with boiling pyridine; naphthaquinoxaline and naphtha-azaquinoxaline derivatives by the reaction with 1,2-diamines and dialkyltin dilapacholates by the reaction with dialkyltin diisopropoxides have been accomplished. Notably the syntheses of rhinacanthin-A, β-(1-hydroxyisopropanyl)-dihydrofurano-1,2-naphthoquinone, dehydroiso-α-lapachone, dehydroiso-β-lapachone, adenophyllone and quadrllone have been reported for the first time from our group starting from lapachol. The synthesis of novel naphthaquinoxaline and azaquinoxaline derivatives from lapachol has been additional interesting results of this investigation.
