alexa beta-Lapachone: synthesis of derivatives and activities in tumor models.
Pharmaceutical Sciences

Pharmaceutical Sciences

Medicinal & Aromatic Plants

Author(s): SchaffnerSabba K, SchmidtRuppin KH, Wehrli W, Schuerch AR, Wasley JW

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Abstract In order to find a 3,4-dihydro-2H-naphtho[1,2-b]pyran-5,6-dione more potent than the naturally occurring 2,2-dimethyl derivative [beta-lapachone (10a)], we synthesized a series of analogous compounds with modifications at position 2 of the pyran ring or at positions 8 and 9 of the benzene ring. Of the compounds tested in vitro for inhibition of RNA-dependent DNA polymerase and in mice infected with Rauscher leukemia, all retained good enzyme activity. Inhibition of the reverse transcriptase activity of the 2,2-substituted derivatives 10b-e was as strong as 10a. However, only the 2-methyl-2-phenyl derivative 10e proved to be about as potent as the 2,2-dimethyl reference compound 10a in prolonging the mean survival time of mice with Rauscher leukemia virus induced leukemia.
This article was published in J Med Chem and referenced in Medicinal & Aromatic Plants

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