New cytotoxic diterpenylnaphthohydroquinone derivatives obtained from a natural diterpenoid

Diterpenylquinone/hydroquinone derivatives were prepared through Diels–Alder cycloaddition between natural myrcecommunic acid or its methyl ester and p-benzoquinone ( p-BQ), using BF 3·Et 2O as catalyst or under microwave (Mw) irradiation. Acetyl, methyl and benzyl derivatives of several diterpenyln...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2007-09, Vol.15 (17), p.5760-5774
Main Authors: Miguel del Corral, José M., Castro, M. Angeles, Lucena Rodrı´guez, M., Chamorro, Pablo, Cuevas, Carmen, San Feliciano, Arturo
Format: Article
Language:English
Subjects:
Acetylation
Allylic oxidation
Antineoplastic agents
Benzene - chemistry
Biological and medical sciences
Biological Products - chemistry
Cell Line, Tumor
Cell Proliferation - drug effects
Cytotoxicity
Diterpenes - chemistry
Drug Screening Assays, Antitumor
General aspects
Humans
Hydroquinones - chemical synthesis
Hydroquinones - chemistry
Hydroquinones - toxicity
Magnetic Resonance Spectroscopy
Medical sciences
Methylation
Molecular Structure
Myrcecommunic acid
Oxidation-Reduction
Pharmacology. Drug treatments
Structure-Activity Relationship
Terpenylquinones
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Summary:Diterpenylquinone/hydroquinone derivatives were prepared through Diels–Alder cycloaddition between natural myrcecommunic acid or its methyl ester and p-benzoquinone ( p-BQ), using BF 3·Et 2O as catalyst or under microwave (Mw) irradiation. Acetyl, methyl and benzyl derivatives of several diterpenylnaphthohydroquinone were prepared from cycloadducts following two basic synthetic strategies, either protection before aromatisation or viceversa. Some of them were further functionalised at the B-ring of the decaline core. Most of the new compounds were evaluated and some of them resulted cytotoxic against several tumour cell lines with IC 50 values under the μM level.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2007.06.005