Synthesis and antitumor activity of diterpenylhydroquinone derivatives of natural ent-labdanes.
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.
Catalán
Luis Espinoza
LE
Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso, Chile. luis.espinozac@usm.cl
Maturana
Evelyn Baeza
EB
Marín
Karen Catalán
KC
Olivares
Mauricio Osorio
MO
Altamirano
Héctor Carrasco
HC
Fritis
Mauricio Cuellar
MC
García
Joan Villena
JV
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
D000970:Antineoplastic Agents; D004224:Diterpenes; D006873:Hydroquinones