Abstract
A synthetic method to obtain α- and β-pyran naphthoquinones 10 and 11 with a hydroxyl substituent on the aromatic ring was developed. Two series of α- and β-pyran naphthoquinones were obtained from the 8-hydroxy-lawsone, and their anticancer properties were evaluated against four tumor cell lines. In general, the new compounds displayed good activity, possibly indicating that these compounds have increased pro-oxidant capacity. The 9-hydroxy-α-lapachone and 7-hydroxy-β-lapachone analogues of the natural products α-lapachone and β-lapachone were successfully produced by this methodology.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology*
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Benzopyrans / chemical synthesis
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Benzopyrans / chemistry
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Benzopyrans / pharmacology*
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Crystallography, X-Ray
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Dose-Response Relationship, Drug
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Drug Screening Assays, Antitumor
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Humans
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Hydrophobic and Hydrophilic Interactions
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Models, Molecular
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Molecular Structure
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Naphthoquinones / chemical synthesis
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Naphthoquinones / chemistry
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Naphthoquinones / pharmacology*
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Antineoplastic Agents
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Benzopyrans
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Naphthoquinones