Synthesis of Naphthoquinoles as Potential Antitumor Agents Related to Jacaranone

Abstract
Naphthoquinols 3a, 3b and 3c [methyl(1,4-dihydro-4-oxo-1-hydroxy-1-naphthalene)acetate, methyl(1,4-dihydro-4-oxo-3-methoxy-1-hydroxy-1-naphthalene)acetate and methyl(1,4-dihydro-4-oxo-3-methyl-l-hydroxy-l-naphthalene)acetate, respectively] were synthesized from the corresponding naphthoquinones by the series of reactions, protection of 1 carbonyl with trimethylsilycyanide, reaction with the enolate of methyl acetate and hydrolytic deprotection with aqueous silver fluoride. These naphthoquinols, which are related to the antitumor compound jacaranone [isolated from Jacaranda caucan], were tesed for cyctotoxicity [using the humor oral carcinosarcoma KB cell system], and found to be inactive.

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