Synthesis of beta-lapachone and its intermediates

Details Synthesis of beta-lapachone and its intermediates Synthesis of beta-lapachone and its intermediates

C - Chemistry, Metallurgy

07

D

C07D 311/92 (2006.01)

Patent

CA 2436125

A novel process for synthesizing .beta.-lapachone (beta-lapachone), an agent that has demonstrated significant antineoplastic activity against human cancer lines. The process comprises the conversion of starting material, 2-hydroxy- 1,4-naphothoquinone into .beta.-lapachone intermediate, lapachol. The lapachol is then converted to .beta.-lapachone by treatment with sulfuric acid and purified by recrystallization from ethanol. This novel process is extremely simple and provides .beta.-lapachone in excellent quality and high yield.

La présente invention concerne un nouveau processus de synthèse de .beta.-lapachone (bêta-lapachone), agent ayant démontré une activité antinéoplastique importante contre des lignées de cancer humain. Ce processus consiste à transformer un matériau de départ, 2-hydroxy-1,4-naphotoquinone en intermédiaire de .beta.-lapachone, le lapachol. Ce lapachol est ensuite transformé en .beta.-lapachone par un traitement à l'acide sulfurique, puis il est purifié par une recristallisation à partir d'éthanol. Ce nouveau processus est extrêmement simple et permet d'obtenir du .beta.-lapachone d'excellente qualité à haut rendement.

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