25 junio 2007
New cytotoxic diterpenylnaphthohydroquinone derivatives obtained from a natural diterpenoid.
Junio 2007 .
New cytotoxic diterpenylnaphthohydroquinone derivatives obtained from a natural diterpenoid.
Miguel Del Corral JM, Castro MA, Lucena Rodrı Guez M, Chamorro P, Cuevas C, San Feliciano A
Departamento de Quı´mica Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, E-37007 Salamanca, Spain.
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(2)O 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 muM level.
New cytotoxic diterpenylnaphthohydroquinone derivatives obtained from a natural diterpenoid.
Miguel Del Corral JM, Castro MA, Lucena Rodrı Guez M, Chamorro P, Cuevas C, San Feliciano A
Departamento de Quı´mica Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, E-37007 Salamanca, Spain.
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(2)O 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 muM level.
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