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Abstract:

Five new 28-homobrassinosteroids have been synthesized, namely, (22R,23R)-5-fluoro-3α,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-3β,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-2α,3α,22,23-tetrahydroxy-5α-stigmastan-6-one, (22R,23R)-3α,5,22,23-tetrahydroxy-5α-stigmastan-6-one and (22R,23R)-3β,5,22,23-tetrahydroxy-5α-stigmastan-6-one. Their bioactivities were evaluated by the rice lamina inclination test. C-5α Fluorinated analogs showed excellent in vitro bioactivity, also revealed at low doses, while C-5α hydroxylated analogs resulted in an important decrease in bioactivity. Previously given explanations to justify the decreasing effect due to C-5α electronegative groups should be revised. (C) 2000 Elsevier Science Ltd.

Registro:

Documento: Artículo
Título:Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs
Autor:Ramírez, J.A.; Gros, E.G.; Galagovsky, L.R.
Filiación:Departamento De Química Orgánica, Facultad De Ciencias Exactas Y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Bioactivity; Brassinosteroids; C-5 fluorinated analogs; C-5 hydroxylated analogs; brassinolide; brassinosteroid; phytohormone; article; chemical structure; hydrogen bond; molecular model; nonhuman; nuclear magnetic resonance; priority journal; reaction analysis; structure activity relation; structure analysis; synthesis
Año:2000
Volumen:56
Número:34
Página de inicio:6171
Página de fin:6180
DOI: http://dx.doi.org/10.1016/S0040-4020(00)00582-2
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v56_n34_p6171_Ramirez

Referencias:

  • Grove, M.D., Spencer, G.F., Rohwedder, W.K., Mandava, N., Worley, J.F., Warthen J.D., Jr., Steffens, G.L., Cook J.C., Jr., (1979) Nature, 281, p. 216
  • (1991), Brassinosteroids: Chemistry, Bioactivity and Applications, Cutler, H. G., Yokota, T., Adam, G., Eds.; American Chemical Society: Washington DC; Back, T.G., (1995), 16, pp. 231-264. , Studies in Natural Products Chemistry, Atta-ur-Rahman, Ed.; Elsevier: Amsterdam; Adam, G., Porzel, A., Schmidt, J., Schneider, B., Voigt, B., (1996), 18, pp. 495-549. , Studies in Natural Products Chemistry, Atta-ur-Rahman, Ed.; Elsevier: Amsterdam; Adam, G., Marquardt, V., (1986) Phytochemistry, 25, p. 1787
  • Arteca, R.N., (1995), pp. 206-213. , Plant Hormones; Davis P.J., Ed.; Kluwer: New York; Mandava, N.B., (1998) Ann. Rev. Plant Physiol. Mol. Biol., 39, pp. 23-53
  • Fujioka, S., (1993) Plant Growth Regul, 13, p. 147
  • Li, J., Nagpal, P., Vitart, V., McMorris, T.C., Chory, J., (1996) Science, 272, pp. 398-401
  • Clouse, S.D., (1996) Plant J, 10, p. 1
  • Clouse, S.D., Langford, M., McMorris, T.C., (1996) Plant Physiol, 111, p. 671
  • Kauschmann, A., Jessop, A., Koncz, C., Szekeres, M., Willmitzer, L., Altmann, T., (1996) Plant J, 9, p. 701
  • Brosa, C., Capdevila, J.M., Zamora, I., (1996) Tetrahedron, 52, p. 2435
  • Takatsuto, S., Yazawa, N., Ikekawa, N., Takematsu, T., Takeuchi, Y., Koguchi, M., (1983) Phytochemistry, 22, p. 2437
  • Thompson, M.J., Meudt, W.J., Mandava, N.V., Dutky, S.R., Lusby, W.R., Spaulding, D.W., (1982) Steroids, 39, p. 89
  • Mori, K., (1992), pp. 317-340. , Molecular structure and Biological Activity os Steroids; Bohl, M., Daux, W. L., Eds.; CRC: Boca Raton, FL; Baron, D.L., Luo, W., Janzen, L., Pharis, R.P., Back, T.G., (1998) Phytochemistry, 49, p. 637
  • Yokota, T., Ogino, Y., Takahashi, N., Saimoto, H., Fujioka, S., Sakurai, A., (1990) Agric. Biol. Chem., 54, p. 1107
  • Seto, H., Fujioka, S., Koshino, H., Yoshida, S., (1999) Tetrahedron, 55, pp. 8341-8352
  • Brosa, C., Soca, L., Terricabras, E., Ferrer, J.C., Alsina, A., (1998) Tetrahedron, 54, pp. 12337-12348
  • Brosa, C., Zamora, I., Terricabras, E., Soca, L., Peracaula, R., Rodriguez-Santamarta, C., (1997) Lipids, 32 (12), pp. 1341-1347
  • Welch, J.T., (1987) Tetrahedron, 33, pp. 3123-3197
  • Takeno, K., Pharis, R.P., (1982) Plant Cell Physiol, 23, pp. 1275-1281
  • Ramirez, J.A., Teme Centurion, O.M., Gros, E.G., Galagovsky, L.R., (2000) Steroids, 65 (6), pp. 329-337
  • Kolb, H., VanNieuwenhze, S., Sharpless, K., (1994) Chem. Rev., 94, pp. 2483-2547
  • Joseph-Nathan, P., Espineira, J., Santillan, R., (1984) Spectrochimica Acta, 40 A, pp. 347-349
  • (1997), JAGUAR 3.0, Schrodinger, Inc.: Portland, Oregon; Howard, J., Hoy, V., O'Hagan, D., Smith, G., (1996) Tetrahedron, 38, pp. 12613-12622
  • O'Hagan, D., Rzepa, H., (1997) Chem. Commun., pp. 645-652
  • Dunitz, J., Taylor, R., (1997) Chem. Eur. J., 3, p. 89

Citas:

---------- APA ----------
Ramírez, J.A., Gros, E.G. & Galagovsky, L.R. (2000) . Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs. Tetrahedron, 56(34), 6171-6180.
http://dx.doi.org/10.1016/S0040-4020(00)00582-2
---------- CHICAGO ----------
Ramírez, J.A., Gros, E.G., Galagovsky, L.R. "Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs" . Tetrahedron 56, no. 34 (2000) : 6171-6180.
http://dx.doi.org/10.1016/S0040-4020(00)00582-2
---------- MLA ----------
Ramírez, J.A., Gros, E.G., Galagovsky, L.R. "Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs" . Tetrahedron, vol. 56, no. 34, 2000, pp. 6171-6180.
http://dx.doi.org/10.1016/S0040-4020(00)00582-2
---------- VANCOUVER ----------
Ramírez, J.A., Gros, E.G., Galagovsky, L.R. Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs. Tetrahedron. 2000;56(34):6171-6180.
http://dx.doi.org/10.1016/S0040-4020(00)00582-2