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(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 microM level.
Miguel Del Corral
José M
JM
Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, Salamanca, Spain. jmmcs@usal.es
Castro
M Angeles
MA
Lucena Rodri Guez
M
M
Chamorro
Pablo
P
Cuevas
Carmen
C
San Feliciano
Arturo
A
D000107:Acetylation; D001554:Benzene / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004224:Diterpenes / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013329:Structure-Activity Relationship
D001688:Biological Products; D004224:Diterpenes; D006873:Hydroquinones; D001554:Benzene