15297-93-5

Basic information

• Product Name: 3,4-Dehydro-β-lapachone
• Synonyms: 2,2-Dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione;3,4-Dehydro-β-lapachone;Dehydro-β-lapachone
• CAS NO: 15297-93-5
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25398
• Mol File: 15297-93-5.mol

Chemical Properties

• Boiling Point: 404.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.28±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3,4-Dehydro-β-lapachone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dehydro-β-lapachone(15297-93-5)
• EPA Substance Registry System: 3,4-Dehydro-β-lapachone(15297-93-5)

Safety Data

• Hazardous Substances Data: 15297-93-5(Hazardous Substances Data)

Upstream product

• 84-79-7 Lapachol 
• 15297-92-4 2,2-dimethyl-2H-benzo[g]chromene-5,10-dione 
• 4707-32-8 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 

Relevant articles and documents

Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone

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

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.

PHARMACEUTICAL COMPOSITION FOR TREATMENT AND PREVENTION OF RESTENOSIS

Provided is a pharmaceutical composition for the treatment and/or prevention of restenosis including (a) a therapeutically effective amount of a particular compound represented by Formula 1 and 2, or a pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

PHARMACEUTICAL COMPOSITION FOR THE TREATMENT AND PREVENTION OF DISEASES INVOLVING IMPOTENCE

Disclosed is a pharmaceutical composition for the treatment and/or prevention of erectile dysfunction, comprising (a) a therapeutically effective amount of a compound represented by Formula 1 or 2, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

Conversion of lapachol to array of furano and pyranonaphthoquinone congeners

Chemical conversion of lapachol to α-lapachone, β-lapachone, dehydro-α-lapachone, dehydroiso-α-lapachone and dehydroiso-β- lapachone by reaction with aqueous NaNO2 and glacial AcOH; rhinacanthin-A, stenocarpoquinone-A, stenocarpoquinone-B and its isomer by reaction with meta-chloroperbenzoic acid at 0° for 30 min and dehydro-α-lapachone and dehydro-β-lapachone at 25° for 4 h respectively and di- and tribromo derivatives by reaction with Br2 in chloroform has been reviewed. In most of these reactions prenyl chain cyclises into an oxygen function to give a number of furano and pyrano-naphthoquinone derivatives. Some of these naphthoquinones co-occur with lapachol in the same plant species.

Conversion of Lapachol to Rhinacanthin-A and other Cyclized Products

A facile synthesis of rhinacanthin-A is achieved by the side chain cyclization of lapachol with meta-chloroperbenzoic acid long with stenocarpoquinone-A, stenocarpoquinone-B and its isomer.Keywords: Lapachol, Rhinacanthin-A, Stenocarpoquinone-A, Stenocarpoquinone-B, Dehydro-β-lapachone