Synthesis and cytotoxicity of new heterocyclic terpenylnaphthoquinones

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 prepa...

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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
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Abstract	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.
AbstractList	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. 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.
Author	Gamito, Ana M a Castro, M a Angeles Martín, M a Luz Cuevas, Carmen Miguel del Corral, José M. Gordaliza, Marina Feliciano, Arturo San
Author_xml	– sequence: 1 givenname: José M. surname: Miguel del Corral fullname: Miguel del Corral, José M. email: jmmcs@usal.es organization: Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, E-37007-Salamanca, Spain – sequence: 2 givenname: M a Angeles surname: Castro fullname: Castro, M a Angeles organization: Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, E-37007-Salamanca, Spain – sequence: 3 givenname: Marina surname: Gordaliza fullname: Gordaliza, Marina organization: Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, E-37007-Salamanca, Spain – sequence: 4 givenname: M a Luz surname: Martín fullname: Martín, M a Luz organization: Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, E-37007-Salamanca, Spain – sequence: 5 givenname: Ana M a surname: Gamito fullname: Gamito, Ana M a organization: Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, E-37007-Salamanca, Spain – sequence: 6 givenname: Carmen surname: Cuevas fullname: Cuevas, Carmen organization: PharmaMar S.A. Avda. de los Reyes, 1. P.I. La Mina-Norte, 28770 Colmenar Viejo, Madrid, Spain – sequence: 7 givenname: Arturo San surname: Feliciano fullname: Feliciano, Arturo San organization: Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, E-37007-Salamanca, Spain
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Snippet	Several heterocyclic terpenylnaphthoquinones have been prepared by palladium (II)-catalyzed oxidative cyclization of the corresponding substituted... Several 2-arylamino-, 2-aryloxy- and 2-arylsulfanyl-6(7)-alkyl-1,4-naphthoquinones (NQ) have been prepared and further transformed into the corresponding... Several 2-arylamino-, 2-aryloxy- and 2-arylsulfanyl-6(7)-alkyl-1,4- naphthoquinones (NQ) have been prepared and further transformed into the corresponding...
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SubjectTerms	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
Title	Synthesis and cytotoxicity of new heterocyclic terpenylnaphthoquinones
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