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• 84-79-7 Lapachol 

Relevant academic research and scientific papers

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.

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.

Radermachera xylocarpa: The highly efficient source of lapachol and synthesis of its derivatives

Isolation and characterization of the major chemical constituents from the stem bark of Radermachera xylocarpa. Chloroform extract of the powdered stem bark contains mainly two components: one is lapachol (91.2%) and second is α-lapachone (5.0%), which are reported herewith first time from this plant, in good quantity and purity.

Bromination with N-Bromosuccinimide : Part III - Formation of 3'-Bromo-β-lapachone, Dehydro-iso-β-lapachone and 4'-Bromo-iso-β-lapachone from Lapachol

Lapachol (I), on bromination with N-bromosuccinimide, affords three ortho-naphthoquinone derivatives which have been characterized to be 3'-bromo-β-lapachone (IV), dehydro-iso-β-lapachone (V) and 4'-bromo-iso-β-lapachone (X) on the basis of spectral and chemical studies.