New cytotoxic diterpenylnaphthohydroquinone derivatives obtained from a natural diterpenoid

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• 作者：José ; M. Miguel del Corral ; M. Angeles Castro ; M. Lucena Rodrı ; ´ ; guez ; Pablo Chamorro ; Carmen Cuevas ; Arturo San Feliciano
• 关键词：Terpenylquinones ; Myrcecommunic acid ; Allylic oxidation ; Cytotoxicity
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2007
• 出版时间：1 September 2007
• 年：2007
• 卷：15
• 期：17
• 页码：5760-5774
• 全文大小：314 K

文摘

Diterpenylquinone/hydroquinone derivatives were prepared through Diels–Alder cycloaddition between natural myrcecommunic acid or its methyl ester and p-benzoquinone (p-BQ), using BF₃·Et₂O 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 IC₅₀ values under the μM level.