Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone
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, g...
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2001
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 08918caa a22009737a 4500 | ||
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| 001 | PAPER-1996 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203119.0 | ||
| 008 | 190411s2001 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0035913050 | |
| 024 | 7 | |2 cas |a 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 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JMCMA | ||
| 100 | 1 | |a Di Chenna, P.H. | |
| 245 | 1 | 0 | |a Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone |
| 260 | |c 2001 | ||
| 270 | 1 | 0 | |m Burton, G.; Depto. de Quimica Orgánica, Facultad de Ciencias Exactas, Universidad de Buenos Aires, Pabellón 2, (1428) Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Burnett, A.R., Thomson, R.H., Naturally occurring quinones. Part X. The quinonoid constituents of tabebuia avellanedae (bignoniaceae) (1967) J. Chem. Soc. C, pp. 2100-2104 | ||
| 504 | |a Díaz, F., Medina, J.D., Furanonaphthoquinones from tabebuia ochracea ssp. neochrysanta (1996) J. Nat. Prod., 59, pp. 423-424 | ||
| 504 | |a Planchon, S.M., Wuerzberger, S., Frydman, B., Witiak, D.T., Hutson, P., Church, D.R., Wilding, G., Boothman, D.A., β-Lapachone-mediated apoptosis in human promyelocytic leukemia (HL-60) and human prostate cancer cells: A p53-independent response (1995) Cancer Res., 55, pp. 3706-3711 | ||
| 504 | |a Li, C.J., Wang, C., Pardee, A.B., Induction of apoptosis by β-lapachone in human prostate cancer cells (1995) Cancer Res., 55, pp. 3712-3715 | ||
| 504 | |a Boothman, D.A., Greer, S., Pardee, A.B., Potentiation of halogenated pyrimidine radiosensitizers in human carcinoma cells by β-lapachone (3,4-dihydro-2,2-dimethyl-2h-naphthol-[1,2-b]pyran-5,6-dione) a novel DNA repair inhibitor (1987) Cancer Res., 47, pp. 5361-5366 | ||
| 504 | |a Li, C.J., Averboukh, L., Pardee, A.B., β-lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin (1993) J. Biol. Chem., 268, pp. 22463-22468 | ||
| 504 | |a Frydman, B., Marton, L.J., Sun, J.S., Neder, K., Witiak, D.T., Liu, A.A., Wang, H.-M., Liu, L.F., Induction of DNA topoisomerase II-mediated DNA cleavage by β-lapachone and related naphthoquinones (1997) Cancer Res., 57, pp. 620-627 | ||
| 504 | |a Li, C.J., Li, Y.-Z., Ventura Pinto, A., Pardee, A.B., Potent inhibition of tumor survival in vivo by β-lapachone plus taxol: Combining drugs imposes different artificial checkpoints (1999) Proc. Natl. Acad. Sci. U.S.A., 96, pp. 13369-13374 | ||
| 504 | |a Pink, J.J., Planchon, S.M., Tagliarino, C., Varnes, M.E., Siegel, D., Boothman, D.A., NAD(P)H:Quinone oxidoreductase activity is the principal determinant of β-lapachone cytotoxicity (2000) J. Biol. Chem., 275, pp. 5416-5424 | ||
| 504 | |a Schaffner-Sabba, K., Schmidt-Ruppin, K.H., Wehrli, W., Schuerch, A.R., Wasley, J.W.F., β-Lapachone: Synthesis of derivatives and activities in tumor models (1984) J. Med. Chem., 27, pp. 990-994 | ||
| 504 | |a Dolan, M.E., Frydman, B., Thompson, C.B., Diamond, A.M., Garbiras, B.J., Safa, A.R., Beck, W.T., Marton, L.J., Effects of 1,2-naphthoquinones on human tumor cell growth and lack of cross-resistance with other anticancer agents (1998) Anticancer Drugs, 9, pp. 437-448 | ||
| 504 | |a Muller, K., Sellmer, A., Wiergrebe, W., Potential antipsoriatic agents: Lapacho compounds as potent inhibitors of HaCaT cell growth (1999) J. Nat. Prod., 62, pp. 1134-1136 | ||
| 504 | |a Lown, J.W., Chen, H.-H., Plambeck, J.A., Acton, E.M., Diminished superoxide anion generation by reduced 5-iminodaunorubicin relative to daunorubicin and the relationship to cardiotoxicity of the anthracycline antitumor agents (1979) Biochem. Pharmacol., 28, pp. 2563-2568 | ||
| 504 | |a Benedetti-Doctorovich, V., Burgess, E.M., Lambropoulos, J., Lednicer, D., Van Derveer, D., Zalkow, L., Synthesis of 2-methyl-(z)-4-(phenylimino)naphth[2,3,d]oxazol-9-one, a monoimine quinone with selective toxicity toward cancer cells (1994) J. Med. Chem., 37, pp. 710-712 | ||
| 504 | |a Benedetti-Doctorovich, V., Escola, N., Burton, G., Preparation and NMR characterization of new substituted benzo[a]phenazines (1998) Magn. Reson. Chem., 36, pp. 529-532 | ||
| 504 | |a Boyd, M.R., Paull, K.D., Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen (1995) Drug Dev. Res., 34, pp. 91-109 | ||
| 504 | |a http://dtp.nci.nih.gov; Hollingshead, M.G., Alley, M.C., Camalier, R.F., Abbott, B.J., Mayo, J.G., Malspeis, L., Grever, M.R., In vivo cultivation of tumor cells in hollow fibers (1995) Life Sci., 57, pp. 131-141 | ||
| 504 | |a note; Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Pople, J.A., (1998) Gaussian 98, revision A.7, , Gaussian, Inc.: Pittsburgh, PA | ||
| 504 | |a Sheldrick, G.M., (1997) SHELXS-97. Program for Structure Resolution, , University of Göttingen, Germany | ||
| 504 | |a Sheldrick, G.M., (1997) SHELXL-97. Program for Structure Refinement, , University of Göttingen, Germany | ||
| 504 | |a Sheldrick, G.M., SHELXTL-PC, version 5.0, p. 1994. , Siemens Analytical X-ray Instruments, Inc.: Madison, WI | ||
| 504 | |a Hooker, S.C., The Constitution of Lapachic Acid (Lapachol) and Synthesis of β-Lapachone (1892) J. Chem. Soc., pp. 611-650 | ||
| 520 | 3 | |a 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. |l eng | |
| 593 | |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, (1428) Buenos Aires, Argentina | ||
| 593 | |a Departamento de Física, Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile, Avenida Blanco Encalada 2008, Casilla 487-3, Santiago, Chile | ||
| 593 | |a Departamento de Física, Comisión Nacional de Energía Atómica, Avenida del Libertador 8250, (1429) Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a 2,2 DIMETHYL 6 (4 METHYLPHENYLIMINO) 3,4,5,6 TETRAHYDRO 2H NAPHTHO[1,2 B]OXIN 5 ONE |
| 690 | 1 | 0 | |a 2,2 DIMETHYL 6 PHENYLIMINO 3,4,5,6 TETRAHYDRO 2H NAPHTHO[1,2 B]OXIN 5 ONE |
| 690 | 1 | 0 | |a ANTINEOPLASTIC AGENT |
| 690 | 1 | 0 | |a BETA LAPACHONE DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ANTINEOPLASTIC ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CANCER CELL CULTURE |
| 690 | 1 | 0 | |a CANCER INHIBITION |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a CYTOTOXICITY |
| 690 | 1 | 0 | |a DRUG MECHANISM |
| 690 | 1 | 0 | |a DRUG STRUCTURE |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a HUMAN |
| 690 | 1 | 0 | |a HUMAN CELL |
| 690 | 1 | 0 | |a ANTINEOPLASTIC AGENTS |
| 690 | 1 | 0 | |a CRYSTALLOGRAPHY, X-RAY |
| 690 | 1 | 0 | |a DRUG SCREENING ASSAYS, ANTITUMOR |
| 690 | 1 | 0 | |a HUMANS |
| 690 | 1 | 0 | |a IMINES |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a NAPHTHALENES |
| 690 | 1 | 0 | |a NAPHTHOQUINONES |
| 690 | 1 | 0 | |a PYRANS |
| 690 | 1 | 0 | |a STEREOISOMERISM |
| 690 | 1 | 0 | |a STRUCTURE-ACTIVITY RELATIONSHIP |
| 690 | 1 | 0 | |a TUMOR CELLS, CULTURED |
| 700 | 1 | |a Benedetti-Doctorovich, V. | |
| 700 | 1 | |a Baggio, R.F. | |
| 700 | 1 | |a Garland, M.T. | |
| 700 | 1 | |a Burton, G. | |
| 773 | 0 | |d 2001 |g v. 44 |h pp. 2486-2489 |k n. 15 |p J. Med. Chem. |x 00222623 |w (AR-BaUEN)CENRE-686 |t Journal of Medicinal Chemistry | |
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| 856 | 4 | 0 | |u https://doi.org/10.1021/jm010050u |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00222623_v44_n15_p2486_DiChenna |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222623_v44_n15_p2486_DiChenna |y Registro en la Biblioteca Digital |
| 961 | |a paper_00222623_v44_n15_p2486_DiChenna |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 999 | |c 62949 | ||