Synthesis and isolation of nitro-β-carbolines obtained by nitration of commercial β-carboline alkaloids

Mostrar otras versiones (1)

Nitration of commercial full aromatic β-carboline alkaloids nor-harmane (1), harmane (2), harmine (3), harmol (4), and the 7-acetylated derivative of harmol (5) is described. Advantages and disadvantages of different nitration reagents which involve acidic conditions (HNO3/H+) and neutral conditions...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autor principal: Ponce, M.A
Otros Autores: Erra-Balsells, R.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: HeteroCorporation 2001
Acceso en línea:Registro en Scopus
DOI
Handle
Registro en la Biblioteca Digital
Aporte de:Registro referencial: Solicitar el recurso aquí
Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
LEADER 09782caa a22013217a 4500
001 PAPER-2109
003 AR-BaUEN
005 20230518203130.0
008 190411s2001 xx ||||fo|||| 00| 0 eng|d
024 7 |2 scopus  |a 2-s2.0-0034748379 
024 7 |2 cas  |a ammonium nitrate, 6484-52-2; beta carboline, 244-63-3; carbon 13, 14762-74-4; harman, 486-84-0; harmine, 343-27-1, 442-51-3; harmol, 487-03-6 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a JHTCA 
100 1 |a Ponce, M.A. 
245 1 0 |a Synthesis and isolation of nitro-β-carbolines obtained by nitration of commercial β-carboline alkaloids 
260 |b HeteroCorporation  |c 2001 
270 1 0 |m Erra-Balsells, R.; Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 3 Ciudad Universitaria, 1428 Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
504 |a Marion, L., (1952) The Alkaloids, 2. , eds. R. H. Manske and H. L. Holmes, Academic Press, New York 
504 |a Allen, J.R.F., Holmstedt, B.R., (1980) Phytochemistry, 19, p. 1573 
504 |a Towers, G.H.N., (1984) Can. J. Bot., 62, p. 2900 
504 |a Sen, A.C., Ueno, N., Chakrabarti, B., (1992) Photochem. Photobiol., 55, p. 753 
504 |a Poindexter, E.H., Carpenter, R.D., (1962) Phytochemistry, 1, p. 215 
504 |a Schultes, R.E., (1969) Science, 163, p. 245 
504 |a Ho, B.T., McIsaac, W.M., Walker, K.E., Estevez, V., (1968) J. Pharm. Sci., 57, p. 269 
504 |a Müller, W.E., Fehske, K.J., Borbe, H.O., Wollert, U., Nanz, C., Rommelspacher, H., (1981) Pharm. Biochem. Behav., 14, p. 693 
504 |a Larson, R.A., Marley, K.A., Tuveson, R.W., Berenbaum, M.R., (1988) Photochem. Photobiol., 48, p. 665 
504 |a Hudson, J.B., Graham, E.A., Towers, G.H.H.N., (1986) Photobiol. Photochem., 43, p. 21 
504 |a Chae, K.H., Ham, H.S., (1986) Soc. Bull. Korean Chem., 7, p. 478 
504 |a Erra-Balsells, R., Frasca, A.R., (1983) Tetrahedron, 39, p. 33 
504 |a Muñoz, M.A., Carmona, C., Hidalgo, J., Guardo, P., Balon, M., (1995) Bioorg. Med. Chem., 3, p. 41 
504 |a Duportail, G., (1981) Int. J. Macromol., 3, p. 188 
504 |a Ghiggino, K.P., Skilton, P.F., Thistlethwaite, P.J., (1985) Pohtochem. J., 31, p. 113 
504 |a Pardo, A., Reyman, D., Poyato, J.M.L., Medina, F., (1982) J. Lumin., 42, p. 113 
504 |a Wolfbeis, O.S., Fuerlinger, E., Winstersteiger, R., (1982) Monatsh. Chem., 113, p. 509 
504 |a Wolfbeis, O.S., Fuerlinger, E., (1982) Z. Phys. Chem. N.F., 129, p. 171 
504 |a Tomas Vert, F., Zabala Sanchez, I., Olba Torrent, A., (1983) J. Photochem., 23, p. 355 
504 |a Tomas Vert, F., Zabala Sanchez, I., Olba Torrent, A., (1984) J. Photochem., 26, p. 285 
504 |a Tomas, F., Zabala, I., Olba, A., (1985) J. Photochem., 31, p. 253 
504 |a Biondic, M.C., Erra Balsells, R., (1990) J. Photochem. Photobiol., A: Chemistry, 51, p. 341 
504 |a Biondic, M.C., Erra Balsells, R., (1992) J. Chem. Soc., Perkin Trans. 2, p. 1049 
504 |a Biondic, M.C., Erra Balsells, R., (1993) J. Chem. Soc., Perkin Trans. 2, p. 887 
504 |a Biondic, M.C., Erra Balsells, R., (1994) Photochem. Photobiol., A: Chemistry, 77, p. 149 
504 |a Biondic, M.C., Erra Balsells, R., (1997) J. Chem. Soc., Perkin Trans. 2, p. 1323 
504 |a Biondic, M.C., Erra Balsells, R., (1998) J. Chem. Research (S), 27, p. 114 
504 |a Sakurovs, R., Ghiggino, K.P., (1982) J. Phytochem., 18, p. 1 
504 |a Dias, A.A., Varela, A.P., Miguel, M.D.G., Macanita, A.L., Becker, R.S., (1992) J. Phys. Chem., 96, p. 10290 
504 |a Draxler, S., Lippitsch, M.E., (1993) J. Phys. Chem., 97, p. 11493 
504 |a Balón, M., Hidalgo, J., Guardo, P., Muñoz, M.A., Carmona, C., (1993) J. Chem. Soc., Perkin Trans. 2, p. 99 
504 |a Nonami, H., Fukui, S., Erra-Balsells, R., (1997) J. Mass Spectrom., 32, p. 287 
504 |a Nonami, H., Tanaka, K., Fukuyama, Y., Erra-Balsells, R., (1998) Rapid Commun. Mass Spectrom., 12, p. 285 
504 |a Nonami, H., Orcoyen, M., Fukuyama, Y., Biondic, M.C., Erra-Balsells, R., (1998) An. Asoc. Quim. Argentina, 86, p. 81 
504 |a Iglesias, L.F., Fukuyama, Y., Baldessari, A., Erra-Balsells, R., Nonami, H., (1999) Biotech. Tech., 13, p. 923 
504 |a Eisenberg, P., Erra-Balsells, R., Ishikawa, Y., Lucas, J.C., Mauri, A.N., Nonami, H., Riccardi, C.C., Williams, R.J.J., (2000) Macromolecules, 33, p. 1940 
504 |a Williams, R.J.J., Erra-Balsells, R., Ishikawa, Y., Nonami, H., Adriana, N.M., Riccardi, C.C., (2001) Macrom. Phys. Chem., , in press 
504 |a Orgueira, H.A., Erra-Balsells, R., Nonami, H., Varela, O., (2001) Macromolecules, 34, p. 687 
504 |a Erra-Balsells, R., Kolender, A., Matulewicz, M.C., Nonami, H., Cerezo, A.S., (2000) Carb. Res., 329, p. 157 
504 |a Fritzsche, J., (1848) Justus Liebigs Ann. Chem., 68, p. 355 
504 |a Fritzsche, J., (1853) Justus Liebigs Ann. Chem., 88, p. 329 
504 |a Konovalova, R., Orekhov, A., (1935) Arch. Pharm., 273, p. 156 
504 |a Siddiqui, S., Ahmad, V.U., Khan, M.A., Ismail, S., (1973) Z. Naturforsh. B, 28, p. 486 
504 |a Snyder, H.R., Parmerter, S.M., Katz, L., (1948) J. Am. Chem. Soc., 70, p. 222 
504 |a Lomakin, A.N., Terent'eva, I.V., (1968) Khim. Geterotsikl. Soedin., p. 1041 
504 |a Shirshova, T.I., Terent'eva, I.V., Vember, P.A., Lazur'evskii, G.V., (1972) Chem. Heterocyclic Compound., 8, p. 898 
504 |a Muñoz, M., Balón, M., Hidalgo, J., Carmona, C., Pappalardo, R.R., Marcos, E.S., (1991) J. Chem. Soc., Perkin Trans. 2, p. 1729 
504 |a Sung, Y.-I., Koike, K., Nikaido, T., Ohmoto, T., Sankawa, U., (1984) Chem. Pharm. Bull., 32, p. 1872 
504 |a Saxena, J.P., (1966) Indian J. Chem., 4, p. 148 
504 |a Saxena, J.P., (1968) J. Indian Chem. Soc., 45, p. 628 
504 |a Carmona, C., Muñoz, M.A., Guardo, P., Balón, M., (1995) J. Phys. Org. Chem., 8, p. 559 
504 |a Ho, B.T., Li, K.-C., Walker, K.E., Wayne Tansey, L., Kralik, P.M., Mclsaac, W.M., (1970) J. Pharm. Sci., 59, p. 1445 
504 |a Hagen, T.J., Skolnick, P., Cook, J.M., (1987) J. Med. Chem., 30, p. 750 
504 |a March, J., (1992) Advanced Organic Chemistry, Reactions, Mechanisms, and Structures, 4th ed., 54, p. 4. , John Wiley and Sons, New York 
504 |a Smith, M.B., (1994) Organic Synthesis, , McGraw-Hill, Inc., New York 
504 |a Giziewicz, J., Wnuk, S.F., Robins, J.M., (1999) J. Org. Chem., 64, p. 2149 
504 |a Eckert, F., Rauhut, G., Katritzky, A.R., Steel, P.J., (1999) J. Am. Chem. Soc., 121, p. 6700 
504 |a Chakrabarty, M., Batabyal, A., (1994) Synthetic Communications, 24, p. 1 
504 |a Grossi, L., Strazzari, S., (2000) J. Org. Chem., 65, p. 2748 
504 |a Aulló, J.M., Tomas Vert, F., (1979) An. Quím., 75, p. 11 
504 |a Kyziol, J.B., Daskiewicz, Z., Hetper, J., (1987) Org. Mass Spectrom., 22, p. 39 
504 |a Coutts, R.T., Locock, R.A., Slywka, W.A., (1970) Org. Mass Spectrom., 3, p. 879 
504 |a (1998) HyperChem., , Suite, Autodesk, Inc., Ontario 
504 |a Frisch, J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Pope, J.A., (1998) Gaussian 98W, Revision A.3., Gaussian 98, A.3, , Gaussian Inc., Pittsburgh PA 
520 3 |a Nitration of commercial full aromatic β-carboline alkaloids nor-harmane (1), harmane (2), harmine (3), harmol (4), and the 7-acetylated derivative of harmol (5) is described. Advantages and disadvantages of different nitration reagents which involve acidic conditions (HNO3/H+) and neutral conditions (Cu(NO3)2; ceric ammonium nitrate) are discussed. A complete 1H and 13C-nmr characterization including ms and also uv absorption spectra in neutral and acid media is presented. A detailed ei-ms and ld-tof-ms study is enclosed because the nitro-β-carbolines constitute a new family of β-carboline-like chromophores with potential use as matrix in uv-maldi-tof-ms.  |l eng 
593 |a Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 3 Ciudad Universitaria, 1428 Buenos Aires, Argentina 
690 1 0 |a AMMONIUM NITRATE 
690 1 0 |a BETA CARBOLINE 
690 1 0 |a CARBOLINE DERIVATIVE 
690 1 0 |a CARBON 13 
690 1 0 |a COPPER DERIVATIVE 
690 1 0 |a HARMAN 
690 1 0 |a HARMINE 
690 1 0 |a HARMOL 
690 1 0 |a HARMOL DERIVATIVE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a ARTICLE 
690 1 0 |a DRUG ISOLATION 
690 1 0 |a DRUG SYNTHESIS 
690 1 0 |a LIGHT ABSORPTION 
690 1 0 |a NITRATION 
690 1 0 |a NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY 
690 1 0 |a PROTON NUCLEAR MAGNETIC RESONANCE 
690 1 0 |a REACTION ANALYSIS 
690 1 0 |a ULTRAVIOLET SPECTROSCOPY 
700 1 |a Erra-Balsells, R. 
773 0 |d HeteroCorporation, 2001  |g v. 38  |h pp. 1071-1082  |k n. 5  |p J. Heterocycl. Chem.  |x 0022152X  |w (AR-BaUEN)CENRE-780  |t Journal of Heterocyclic Chemistry 
856 4 1 |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-0034748379&doi=10.1002%2fjhet.5570380510&partnerID=40&md5=d34fcfd137bb5a04fca40471d8cfe19b  |y Registro en Scopus 
856 4 0 |u https://doi.org/10.1002/jhet.5570380510  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_0022152X_v38_n5_p1071_Ponce  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v38_n5_p1071_Ponce  |y Registro en la Biblioteca Digital 
961 |a paper_0022152X_v38_n5_p1071_Ponce  |b paper  |c PE 
962 |a info:eu-repo/semantics/article  |a info:ar-repo/semantics/artículo  |b info:eu-repo/semantics/publishedVersion 
963 |a VARI 
999 |c 63062 

Ejemplares similares