Artículo
Di Chenna, P.H.; Benedetti-Doctorovich, V.; Baggio, R.F.; Garland, M.T.; Burton, G. "Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone" (2001) Journal of Medicinal Chemistry. 44(15):2486-2489
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Abstract:
A regio- and stereospecific synthesis of monoarylimino o-quinones derived from β-lapachone (1) was achieved by treatment of the quinone with a slight excess of an arylamine in the presence of an excess of triethylamine/titanium tetrachloride 4:1. Imine formation occurred exclusively at position 6, giving the Z diastereomer, as determined by single-crystal X-ray analysis. In vitro tests for cytotoxicity in 55 human cancer cell cultures showed a substantial loss in activity for the p-nitrophenylimine (5), whereas the phenylimine (2), p-methylphenylimine (3), and p-methoxyphenylimine (4) retained (or bettered) most of the cytotoxicity and selectivity of the parent quinone. Preliminary in vivo testing in hollow fiber assays against a standard panel of 12 human tumor cell lines showed that although β-lapachone failed, compounds 2 and 3 had good scores with net cell kills.
Registro:
| Documento: | Artículo |
| Título: | Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone |
| Autor: | Di Chenna, P.H.; Benedetti-Doctorovich, V.; Baggio, R.F.; Garland, M.T.; Burton, G. |
| Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, (1428) Buenos Aires, Argentina Departamento de Física, Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile, Avenida Blanco Encalada 2008, Casilla 487-3, Santiago, Chile Departamento de Física, Comisión Nacional de Energía Atómica, Avenida del Libertador 8250, (1429) Buenos Aires, Argentina |
| Palabras clave: | 2,2 dimethyl 6 (4 methylphenylimino) 3,4,5,6 tetrahydro 2h naphtho[1,2 b]oxin 5 one; 2,2 dimethyl 6 phenylimino 3,4,5,6 tetrahydro 2h naphtho[1,2 b]oxin 5 one; antineoplastic agent; beta lapachone derivative; unclassified drug; antineoplastic activity; article; cancer cell culture; cancer inhibition; controlled study; cytotoxicity; drug mechanism; drug structure; drug synthesis; human; human cell; Antineoplastic Agents; Crystallography, X-Ray; Drug Screening Assays, Antitumor; Humans; Imines; Magnetic Resonance Spectroscopy; Naphthalenes; Naphthoquinones; Pyrans; Stereoisomerism; Structure-Activity Relationship; Tumor Cells, Cultured |
| Año: | 2001 |
| Volumen: | 44 |
| Número: | 15 |
| Página de inicio: | 2486 |
| Página de fin: | 2489 |
| DOI: | http://dx.doi.org/10.1021/jm010050u |
| Título revista: | Journal of Medicinal Chemistry |
| Título revista abreviado: | J. Med. Chem. |
| ISSN: | 00222623 |
| CODEN: | JMCMA |
| CAS: | 2,2-dimethyl-6-(4-methylphenylimino)-3,4,5,6-tetrahydro-2H-naphtho(1,2-b)oxin-5-one; 2,2-dimethyl-6-phenylimino-3,4,5,6-tetrahydro-2H-naphtho(1,2-b)oxin-5-one, 0; Antineoplastic Agents; Imines; Naphthalenes; Naphthoquinones; Pyrans; beta-lapachone, 4707-32-8 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222623_v44_n15_p2486_DiChenna |
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Citas:
---------- APA ----------
Di Chenna, P.H., Benedetti-Doctorovich, V., Baggio, R.F., Garland, M.T. & Burton, G. (2001) . Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone. Journal of Medicinal Chemistry, 44(15), 2486-2489.http://dx.doi.org/10.1021/jm010050u
---------- CHICAGO ----------
Di Chenna, P.H., Benedetti-Doctorovich, V., Baggio, R.F., Garland, M.T., Burton, G. "Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone" . Journal of Medicinal Chemistry 44, no. 15 (2001) : 2486-2489.http://dx.doi.org/10.1021/jm010050u
---------- MLA ----------
Di Chenna, P.H., Benedetti-Doctorovich, V., Baggio, R.F., Garland, M.T., Burton, G. "Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone" . Journal of Medicinal Chemistry, vol. 44, no. 15, 2001, pp. 2486-2489.http://dx.doi.org/10.1021/jm010050u
---------- VANCOUVER ----------
Di Chenna, P.H., Benedetti-Doctorovich, V., Baggio, R.F., Garland, M.T., Burton, G. Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone. J. Med. Chem. 2001;44(15):2486-2489.http://dx.doi.org/10.1021/jm010050u
