title: Synthesis and antitumor activity of diterpenylhydroquinone derivatives of natural ent-labdanes.
abstract: Two new compounds 2β-acetoxy-15-phenyl-(22,25-acetoxy)-ent-labda-8(17), 13(E)-diene (9) and 2β-hydroxy-15-phenyl-(22,24,26-trimethoxy)-ent-labda-8(17),13(E)-diene (10) have been prepared by an Electrophilic Aromatic Substitution (EAS) reaction between diterpenyl allylic alcohols and 1,4-hydroquinone or 1,3,5-trimethoxybenzene using BF(3).Et(2)O as a catalyst. These compounds, along with a series of natural ent-labdanes 3-8, have been evaluated for their in vitro cytotoxic activities against cultured human cancer cells of PC-3 and DU-145 human prostate cancer, MCF-7 and MDA-MB-231 breast carcinoma and dermal human fibroblasts (DHF). Some compounds displayed inhibition at µM IC(50 )values.
authors.affiliation: Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso, Chile. luis.espinozac@usm.cl
authors.forename: Luis Espinoza
authors.initials: LE
authors.lastname: Catalán
authors.forename: Evelyn Baeza
authors.initials: EB
authors.lastname: Maturana
authors.forename: Karen Catalán
authors.initials: KC
authors.lastname: Marín
authors.forename: Mauricio Osorio
authors.initials: MO
authors.lastname: Olivares
authors.forename: Héctor Carrasco
authors.initials: HC
authors.lastname: Altamirano
authors.forename: Mauricio Cuellar
authors.initials: MC
authors.lastname: Fritis
authors.forename: Joan Villena
authors.initials: JV
authors.lastname: García
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001943:Breast Neoplasms / Q000188:drug therapy; D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D004224:Diterpenes / Q000737:chemistry*; D005260:Female; D005347:Fibroblasts / Q000187:drug effects; D006801:Humans; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D008297:Male; D011471:Prostatic Neoplasms / Q000188:drug therapy
chemical_list: D000970:Antineoplastic Agents; D004224:Diterpenes; D006873:Hydroquinones