Synthesis and cytotoxicity of new heterocyclic terpenylnaphthoquinones

• Published in: Bioorganic & medicinal chemistry Vol. 14; no. 8; pp. 2816 - 2827
• Main Authors: Miguel del Corral, José M., Castro, M a Angeles, Gordaliza, Marina, Martín, M a Luz, Gamito, Ana M a, Cuevas, Carmen, Feliciano, Arturo San
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 15-04-2006
• Subjects: Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - pharmacology; Benzocarbazoles; Benzonaphthofuranediones; Cell Line, Tumor; Cytotoxicity; Diels–Alder cycloaddition; Drug Screening Assays, Antitumor; Humans; Magnetic Resonance Spectroscopy; Naphthoquinones - chemical synthesis; Naphthoquinones - pharmacology; Spectrometry, Mass, Fast Atom Bombardment; Terpenylquinones; Terpenylquinones; Cytotoxicity; Diels–Alder cycloaddition; Benzonaphthofuranediones; Benzocarbazoles
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2005.12.002

Several heterocyclic terpenylnaphthoquinones have been prepared by palladium (II)-catalyzed oxidative cyclization of the corresponding substituted naphthoquinones and evaluated as antineoplastics.
Several 2-arylamino-, 2-aryloxy- and 2-arylsulfanyl-6(7)-alkyl-1,4-naphthoquinones (NQ) have been prepared and further transformed into the corresponding heterocyclic-fused naphthoquinones by palladium (II)-catalyzed oxidative cyclization. The compounds synthesized have been evaluated against neoplastic cell lines. The extension of the polycyclic system clearly decreased the cytotoxic potency of the 2-substituted terpenylnaphthoquinones.